guided walking tours tuscany italy

Tuscany Walking

Small Group Walking Tours in Tuscany

Welcome to Tuscany Walking.

Small Group Guided Walking Holidays in Tuscany.

We have been guiding walking tour holidays and hiking vacations here in northern Tuscany, Italy, since 2005.

We have a wealth of experience and knowledge of this spectacularly beautiful area of Northern Tuscany, from Lucca, to Castelnuovo di Garfagnana, the Garfagnana National Park and beyond. We have put together a series of inspiring and beautiful walking tours tailor made for all levels of experience and abilities and we would like to them share with you.

Walking with us here at Tuscany Walking, you will experience a taste of the real Italy on your vacation. You will walk through ancient hilltop hamlets, hike in spectacular mountains with stunning views, discover refreshing streams and rivers and experience a natural peace. You will be surrounded by the most stunning scenery, in what is an undiscovered and unspoiled part of Italy.

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Tuscany & the Cinque Terre Culture + Walking

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Drinking in the sunset and the Chianti at our friend Marco's farmhouse, we decided that a Tuscany walking tour couldn't be improved upon. Since he's a staunch Tuscan, he surprised us by saying, "Then you've never been to the Cinque Terre." So we went. They're not far, these five once almost unreachable villages that grow out of rock along the Ligurian Sea. For centuries, a connecting footpath was their lifeline, but for us it's the scenic route into a remote and vibrant coastal culture. Beforehand, we spend three nights in the parts of Tuscany we love best…complete with hilltowns that rise out of silver-green olive groves, homemade prosciutto and potato ravioli and the sunny vineyards of Chianti. Throughout, we'll explore the art history, and savor the food and wine. But in the end, will you prefer walking tours in Tuscany or the Cinque Terre? The good news is that because this trip gives you both, you don't have to decide.

• Gather in Florence, where a short journey into Chianti leads to a private visit and tasting at one of the famed wineries, followed by a scenic walk to our hotel, a historic villa that dates to the 16th century and is owned by a count and countess.

• Walk past silvery olive groves to visit a shepherd who shows how he makes sheep's-milk cheeses…and a chance to sample some of the traditional specialties.

• Follow a footpath in the lovely Chianti hills, to a vineyard walk that ends with a home-cooked lunch and wine-tasting in the private cellars of Castello della Paneretta.

• Spot San Gimignano, fortified with more than a dozen medieval towers, shimmering in the near distance as we approach along a rural footpath.

• Journey along the Apuane mountains to Santa Margherita, where our hotel overlooks the Ligurian Sea.

• Walk to the colorful, isolated villages of the Cinque Terre — Monterosso, Vernazza, Corniglia, Manarola and Rio Maggiore — with time out for shopping or a picnic. (Or skip the walking, and take a little coastal train that runs between the villages.)

• Explore the tiny monastery of San Fruttuoso reachable only by foot or boat after visiting iconic Portofino.

• Cap off an evening in Florence with a memorable dinner at our favorite trattoria, where in one meal we enjoy the whole tapestry of Tuscan cuisine.

• Skip the lines to see Michelangelo's David as part of a guided walk in Florence that provides an insider's view of the famed Renaissance city.

• Wandering the ancient streets to see and learn about Brunelleschi's incredible dome, the Ponte Vecchio, and Piazza della Signoria.

• Graze through San Lorenzo, the Florentine's main market, with its pyramids of produce, olives, breads, meats and more.

Starting Point:

Ending point:.

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Dates & Prices

The earlier you book, the more choice you’ll have and the lower your price. And you can always change your mind — you won’t be charged to transfer to a different trip before your final payment is due. Talk with one of our travel experts at 800-200-3887 .

Select our “Family Departure” to travel with other families.

Why Choose Classic Journeys

• Experience the world on foot and at eye level. Each day, join your guide on the most cinematic footpaths in Tuscany and along the coastal towns of Cinque Terre.
• Exceptional full-time local guides who become your well-connected friend. Our amazing guides are with you throughout each day of the tour, sharing their lifelong connections as well as engaging anecdotes about Italian history and culture.
• Small groups that provide you unrivaled access. An average of fewer than 10 guests per departure means we can offer you special access to sites like skipping the lines to see Michelangelo’s David in Florence, visiting with a shepherd and tasting his sheep’s-milk cheeses and strolling through a vineyard with the owners in Tuscany.
• Award-winning hotels are waiting for you at the end of every day. Luxuriate in the finest and most distinctive accommodations in the region you’re exploring, including a historic villa that dates to the 16th century and is owned by a count and countess.
• Eat like (and with) the locals. Food is a foolproof way into the hearts, homes and history of the places you visit with us. From gourmet picnics to coveted local restaurants, our meals offer you opportunities to explore native food traditions and fine dining.
• Handcrafted itineraries with all activities included. With our long-term friendships, we know our walking tour regions more personally than anyone else. So you get thoughtfully curated itineraries that combine explorations of the villages, organic farms, archeological sites and the people who know them best.
• Sustainable travel that supports the places you’re visiting. We put our local currency into the pockets of the people who live where we travel. It’s your guarantee that you’ll have authentic, up-close experiences on your trip. Best of all, our person-to-person approach helps sustain their ways of life.

Accommodations

We spend years cultivating personal relationships with our hoteliers to provide you thoughtfully selected accommodations that reveal the true character of the region. Here is a sampling of our favorite hotels on this tour. 

Grand Hotel Miramare

One of the first grand hotels in the region, this property is a Leading Hotel of the World. It offers all of the luxurious comfort you expect…plus a pool that overlooks the scenic promenade to Portofino.

Antica Torre Di Via Tornabuoni

Originally a palace of the Guelf family, this historic hotel in the heart of Florence is known for its attentive service. The rooftop terraces offer remarkable views of the entire city. Rooms are decorated in elegantly understated Florentine style.

Villa Le Barone

This historic home dates to the 16th century, and your hosts are a count and countess. Its rooms have wood-beamed ceilings and antiques. The property boasts lovely gardens, a new saltwater infinity pool, and a terrace for sunning and Chianti sipping.

What’s Included

• Award-winning boutique hotels that provide you unlimited access to the people and places, culture and history you came to experience
• All breakfasts, 1 lunch and 5 dinners
• Full-time experienced guide(s) who are with you throughout the trip, handle behind-the-scenes logistics 
• Admissions to sites and other scheduled events as noted in the detailed daily itinerary
• Gratuities for hotels, meals and baggage
• All land transportation during the trip

Above & Beyond Benefits

Perfect pairings dinners.

• A special dinner prepared by one of our favorite chefs with a procession of wines tailored to each course.

Invisible Check-In

• When your group arrives, we whisk you and your bags to your room immediately. No waiting – no tipping.

Privileged Access Events

• One-of-a-kind access to remarkable people, places and activities arranged just for you.
• In many regions, we uncork wonderful local wines at every dinner, compliments of Classic Journeys.

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Tuscany Walking Holidays

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Montepulciano to Siena Walking Holidays

Chianti Walking Holidays

Via Francigena Highlights

Walking Holidays in Tuscany and Umbria

Luxury Walking Holidays Tuscany

About Tuscany Walking Holidays

Step into the world of Tuscany Walking Holidays, where the  rolling hills  whisper tales of the past and the  cypress trees  sway in rhythm with the wind.

Our walking holidays are tailored to suit every pace and preference —  from demanding to easy  walking holidays in Tuscany. Whether you’re seeking a leisurely stroll through the vineyards of  Chianti  or a more challenging hike up the rugged hills of the  Apuan Alps , we’ve got you covered.

So, stop and think for a minute: isn’t it about time that you experience the authentic tastes of Tuscany, from the famous Pecorino cheese of  Pienza  to the exquisite wines of  Montepulciano ?

We’ll handle all the logistics, from booking comfortable  accommodations  to arranging  transfers  for you and your luggage. As such, you can immerse yourself in the local culture without a worry in the world.

On our self-guided walking tours in Tuscany, we equip you with a  personalised booklet  containing a detailed itinerary,  GPS navigation  for your hikes, and recommendations for the best local experiences.

Or, we can  provide a guide  upon request. With Tuscany Walking Holidays, stress-free travel isn’t just a promise — it’s a guarantee.

Tuscany’s Must-Visit Towns

1. florence.

The cradle of the Renaissance, Florence is a treasure trove of art and architecture.

Known for its mediaeval brick buildings and the famous Palio horse race, Siena is a step back in time.

3. Montepulciano

Nestled among rolling hills, Montepulciano is renowned for its Renaissance architecture and exquisite wine.

A UNESCO World Heritage site, Pienza is a jewel of Renaissance architecture with stunning views of the Val d’Orcia and the best Pecorino cheese in the entire Italy.

5. San Gimignano

Known as the Manhattan of the Middle Ages, San Gimignano’s skyline is punctuated by towering mediaeval skyscrapers.

The Allure of Walking in Tuscany

Tuscany, a region steeped in history and culture, is a tapestry of  ancient towns ,  vineyard-laden hills , and  sun-drenched fields . Picture yourself wandering through the cobblestone streets of  Florence , the heart of the Renaissance, or exploring the mediaeval charm of  Siena , where every street is a journey back in time.

This is the land of the  Renaissance , Chianti wine, and landscapes that have inspired artists for centuries — from  Leonardo da Vinci to Michelangelo .

As you pass through the ancient villages, you’ll be captivated by the  rich tapestry of history  unfolding before your eyes. Each stone, each path, and each building tells a story of a time long past yet still very much alive in the hearts and minds of the locals. Just imagine stepping into the world of Tuscany, a world where history whispers in the wind and beauty blooms in every corner.

HASSLE-FREE

Trusted by many, tried & tested adventures, unbeatable support, things to know.

Our walking holidays in Tuscany are primarily focused on leisurely exploration, offering a delightful experience without significant elevation gain. However, it’s important to note that certain stages of the Via Francigena can be quite long. In addition, we also offer other holiday options that include more demanding hikes. Regardless of the holiday you choose, we aim to provide a high-quality experience catering to different fitness levels. So, whether you prefer leisurely strolls through the picturesque Tuscan countryside or more demanding hikes to push your limits, we have options to suit your preferences and ensure a fulfilling journey.

Absolutely! Our hiking holidays are designed to be inclusive and can be enjoyed by people of various age groups, including children. Most of our tours do not include technically demanding terrain. We believe in the importance of providing opportunities for children to embrace the outdoors and experience the joys of hiking. While a minimum age of eight is recommended to ensure safety and engagement, our tours are generally suitable for individuals who possess basic physical capabilities and can comfortably walk for a few hours daily.

For our walking tours, we highly recommend wearing sturdier hiking shoes that provide ample support, particularly during long hiking days and on uneven terrain. Hiking shoes are designed specifically for outdoor activities, offering features such as sturdy soles, enhanced traction, and ankle support. They are well-suited to handle various terrains, including gravel paths, rocky trails, and uneven surfaces commonly encountered during our walking tours. Opting for appropriate footwear ensures comfort and stability and minimises the risk of foot fatigue or potential injuries.

We highly recommend making an advance booking to ensure accommodation availability. Securing your reservation early increases the likelihood of obtaining your preferred options. If you wait until the start of the season or during the season, availability in hotels and apartments may be limited, and we may not be able to guarantee your desired arrangements.

It’s important to be aware that accommodations at the destinations are in high demand, especially during the summer season. To secure your preferred type of housing, we strongly recommend booking early. By doing so, you increase the likelihood of obtaining the accommodation that best suits your preferences. While the availability of specific lodging options may vary, we assure you that we will make every effort to provide you with the most suitable accommodations based on your preferences. Our team is dedicated to ensuring your stay is comfortable and enjoyable, and we strive to meet your specific requirements to the best of our ability.

Our tours are meticulously planned and designed to be easily navigated by independent travelers. The destinations are well-marked and accessible, allowing you to explore at your own pace. As such, it is unlikely that you will require a guide during your tour.

To ensure you have all the necessary information and guidance, we provide a comprehensive handout that covers essential details about the routes, points of interest, and practical tips. This enables you to enjoy the freedom and flexibility of a self-guided holiday, where you can fully immerse yourself in the experience and discover the beauty of each destination at your leisure.

However, if you prefer to have a guide accompany you during the tours, we are more than happy to accommodate your request. Simply let us know in advance, and we will make the necessary arrangements to provide you with a knowledgeable guide who can enhance your journey with insightful commentary and assistance.

The best time to go on a walking holiday in Tuscany is during the early spring and fall seasons. During these periods, the weather is pleasant, and the crowds are fewer, allowing for a more tranquil and enjoyable experience.

In the early spring, typically from March to May , you can witness the region come alive with vibrant blossoms and lush greenery. The temperatures are mild, making it perfect for exploring the picturesque landscapes of Tuscany on foot. Additionally, the tourist crowds are relatively smaller during this time, providing you with a more intimate and serene setting to immerse yourself in the beauty of the surroundings.

Similarly, the fall season, from September to November , offers a delightful time to visit. The weather remains pleasant, with comfortable temperatures ideal for walking and exploring. The autumn colours add a captivating charm to the landscapes, creating a picturesque backdrop for your walking tour. With fewer visitors compared to the peak summer months, you can fully appreciate the tranquillity and authenticity of the region.

It’s worth noting that the summer months in Tuscany, particularly July, and August, can be quite hot and crowded . While the region maintains its allure during this time, the higher temperatures and increased tourist influx may impact your overall experience. However, if you plan accordingly and take precautions against the heat and the crowds, summer can still offer enjoyable walking opportunities in Tuscany.

In cases of light rain or mild weather disturbances, hiking can often still be safely managed as long as it does not pose any significant risks. The stunning landscapes of Tuscany can take on a unique charm under a drizzle, offering a different perspective and an enchanting experience.

However, in situations where the weather becomes more severe, such as heavy rainstorms or thunderstorms, our team will assess the situation and make appropriate adjustments to ensure your safety. This may involve modifying the planned routes, seeking shelter, or postponing the activity until the weather improves.

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Overview    Inclusions    Itinerary    Price    Reviews

Scheduled tours

• May 1-7 – only upon request (a lady from Namibia seeks room share…interested?)
• May 22-28 – (sold out)
• June 5-11 – places available (a lady from South Africa seeks room share…interested?)
• Sept 11-17 – places available
• Sept 25-Oct 1 (2 places available)
• Oct 2-8 (sold out)
• Oct 12-18 – places available

Private tours

price p/p: varies according to group size. Check Price below here

Departures: anytime

  [email protected]

Book 2025 tours before wed april 24 and save 100 euro.

PRIVATE GROUP SIZE: min 1 – no limit DURATION: 7 Days & 6 Nights

  WALK RATING: 2+

⇑ CLOSEST AIRPORTS: Florence (FLR) and Rome (FCO)

Overview on Tuscany Walking Tour

Embark on a Journey Through Tuscany

Explore Tuscany’s medieval towns and countryside with our guided walking tour. Discover Siena, Chianti, and San Gimignano. Enjoy leisurely strolls, family-run hotels, culinary delights, and local interactions. Choose between small group or private excursions for an unforgettable adventure.

Discover the Timeless Charms

Unveil Tuscany’s hidden gems: Siena, Chianti, San Gimignano, Montalcino, Pienza, and Val d’Orcia. Embarking on the Tuscany walking tour, you will wander ancient streets, savor regional delicacies, and soak up vibrant culture.

A Leisurely Pace, Enriching Stops

Stroll for 2-3 hours daily, indulging in guide commentaries and local attractions. Experience personalized hospitality at family-run hotels.

Culinary Delights and Musical Notes

Savor lunches at family-run farms and dinners at cozy trattorias. It’s a gourmet tour! Enjoy occasional musical accompaniments.

A Tapestry of People and Memories

Engage with locals for authentic interactions and lasting connections.

Your Way to Explore

Choose small group or private excursions for a tailored experience.

  6 night stay at small hotels (3 and 4 stars). Book early and we will try to accommodate you in a room with a view.

  All breakfasts, 5 lunches, 4 dinners. Local wine is always included with lunches and dinners. Vegetarian? Vegan? No problem!

  Transportation along the tour

  We carry your luggage from hotel to hotel

1 local guide for groups smaller than 10. Groups larger than 10 people will be guided by 2 local guides.

Entrance tickets for all the special events

   Chianti wine tasting and winery visit: you will talk to the owner!

  Learn about saffron making or cheese making (according to availability) at a small farmhouse in Pienza

  Learn how to tell the quality of extra virgin olive oil along an olive oil tasting

Full cooking class in an ancient building. A lot of fun!

  All taxes

Itinerary of Tuscany Walking Tour

tuscany walking tour map

Gathering at the hotel’s lobby at 4:00 pm, we’ll commence our journey with an insightful tour introduction. Joined by an art guide, we’ll delve into Siena’s treasures – from the enchanting Piazza del Campo to winding alleys and the Palio horse race district’s museum. A delightful dining experience awaits at the family-owned Babazuf, where Marco and Chef Giovanni fuse traditional and modern Italian flavors. 6 km = 3,7 miles (town stroll) ***La Villa Hotel – Siena dinner

Day 2 – Chianti Unveiled: Walk and Winery (Overnight at La Villa Hotel, Siena)

Our adventure unfolds through Chianti’s renowned vineyards and olive groves. At the intimate Fattoria Tregole winery, hosted by Dario Castagno, NYTimes Bestselling author, you’ll explore this organic haven nestled in Chianti Classico’s heart. Dario’s vivacious accounts, steeped in history, enhance the experience. A delectable lunch at the winery’s restaurant precedes a transfer to Siena. Later, immerse yourself in a captivating cooking class at Dante Alighieri cooking school. 8 km = 5 miles ***La Villa Hotel – Siena breakfast – lunch – dinner

SHOW DAY 3, 4, 5, 6, 7

Venture to San Gimignano, a 45-minute transfer away. The town boasts 14 towering medieval marvels. Our countryside hike, enriched by olive groves and Vernaccia di Sangimginano vineyards, leads to Ganozzi family’s vegetable garden farmhouse. A delightful lunch sourced from their produce awaits. Returning to Siena, dinner is at your leisure.

11 km = 7 miles with shorter options ***La Villa Hotel – Siena breakfast – lunch

Day 4 – Montalcino and Brunello Experience (Corsignano Hotel in Pienza)

A 50-minute drive takes us to Montalcino, famed for its wines. Wander its charming streets before embarking on a woodland walk. The path, adorned with Monte Amiata views, leads to Giacomo’s Il Cocco farm. Delve into wine wisdom with Giacomo as you explore his vineyard, Brunello in hand. A farm-fresh lunch follows. Transition to Pienza’s Corsignano Hotel. Tonight, savor dinner at a delectable Pienza eatery.

9 km = 5.5 miles – optional afternoon walk of 4 Km = 2.5 miles Corsignano Hotel in Pienza breakfast – lunch, dinner

Day 5 – Bagno Vignoni to San Quirico (Corsignano Hotel in Pienza)

A short 15-minute transfer delivers us to Bagno Vignoni. After visiting, we embark on a 4-mile journey to the less-trodden San Quirico d’Orcia. Lunch at Osenna educates on quality olive oil and treats you to hand-made pici pasta with truffles. Explore San Quirico and its gardens before returning to Pienza. Dinner is yours to choose.

9 km = 5,5 miles Corsignano Hotel in Pienza breakfast – lunch, dinner

Day 6   Pienza walk to the farm – saffron farm or cheese making farm

Set forth on foot from the hotel to Monticchiello, walking through wheat fields. Arrive at Santa Maria Farmhouse, specializing in saffron. Savor a sumptuous lunch celebrating local flavors and produce. Choose to return by foot or enjoy a drive back. The grand farewell dinner unfolds at an elegant international/Tuscany fusion restaurant.

* during some tours we instead go to   Il Casale cheese farm, nearby Monticchiello, according to the availability. Sandra will show us how they make pecorino sheep cheese: from the 10 day aged cheese to 20 months old cheese. The sheep are raised in this farm from generations. A nice lunch based on pasta, pecorino (of course!) and local wine will follow. You can decide to be driven back to the hotel or join your guide and walk back to the hotel.

9 km = 5,5 miles – optional afternoon walk of 7 Km = 4,3 miles   ****Corsignano Hotel – Pienza breakfast, lunch, dinner

Day 7 – Farewell

At 9:00 am, a 45-minute drive takes you to Chiusi-Chianciano Terme train station. From here, a train journey of about two hours leads you to Florence or Rome.

note on the itinerary

FOOD OF TUSCANY WALKING TOUR

Here are some examples of what you’ll be eating and drinking, during the tour. It’s a gourmet experience!

Pici pasta is a type of traditional Italian pasta that originates from the Tuscany region. It’s characterized by its unique shape and rustic appearance.

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Pici pasta is hand-rolled and typically made from just two simple ingredients: flour and water. The dough is rolled into thick, long strands that resemble rustic spaghetti. What sets pici pasta apart is its slightly uneven and thick texture, which allows it to hold onto sauces quite effectively. The width of pici can vary, but it’s generally wider than standard spaghetti and has a chewy, hearty consistency when cooked. It’s often served with various sauces, such as tomato-based sauces, ragù, or simple garlic and olive oil, making it a versatile canvas for different flavor profiles.

Panzanella is a traditional Italian salad that originates from Tuscany. It is a delightful and rustic dish made primarily from simple ingredients like stale bread, ripe tomatoes, onions, fresh basil, cucumbers, and sometimes bell peppers. 

The bread is a key component, as it’s typically soaked or lightly toasted to bring out its flavors and textures. The bread absorbs the juices from the tomatoes and any dressing used, making it soft and flavorful. The tomatoes provide a burst of freshness and juiciness, while the onions add a mild bite. Fresh basil contributes a fragrant and aromatic element, enhancing the overall taste. Additional vegetables like cucumbers and bell peppers can be added for extra crunch and color.

Panzanella is often seasoned with olive oil, vinegar (typically red wine vinegar), salt, and pepper. The dressing complements the natural flavors of the ingredients and ties them together into a harmonious and satisfying dish. It’s a perfect example of Italian cuisine’s knack for turning simple, humble ingredients into a delicious and satisfying meal.

Bruschetta and cold cuts (affettati)

Bruschetta is an Italian appetizer or antipasto dish that consists of toasted slices of crusty bread, typically made from rustic or country-style bread.

The bread slices are often rubbed with garlic and drizzled with olive oil before being toasted or grilled until they become crispy and slightly charred. Once the bread is prepared, it’s commonly topped with a mixture of fresh ingredients, which can vary but typically includes diced tomatoes, fresh basil, garlic, and sometimes onions. The toppings are seasoned with salt, pepper, and additional olive oil to enhance the flavors. Bruschetta is known for its delightful combination of textures and flavors, offering a satisfying contrast between the crunchy bread and the fresh, aromatic toppings. It’s often served as an appetizer at Italian restaurants and is enjoyed for its simplicity, vibrant taste, and the use of high-quality, fresh ingredients.

Affettati is an Italian culinary term that refers to a variety of sliced, cured meats. These meats are typically thinly sliced and are often served as an appetizer or antipasto dish. Common types of affettati include prosciutto (cured ham), salami (cured sausage), bresaola (air-dried beef), and coppa (cured pork shoulder). The term “affettati” comes from the Italian word “affettare,” which means “to slice,” highlighting the importance of the thin slicing technique used to prepare these meats. These delicacies are enjoyed for their rich flavors and are often accompanied by cheeses, olives, and other accompaniments as part of a charcuterie board or platter.

Costoleccio e salsicce Arrosto

Brunello di Montalcino

Brunello di Montalcino is a type of red wine that comes from the Montalcino region in Tuscany, Italy. It’s known for its exceptional quality and is considered one of Italy’s finest and most renowned wines.

Other Details

The wine is made exclusively from Sangiovese grapes, a traditional Italian grape variety known for its rich flavors and ability to reflect the characteristics of the terroir (environmental factors that influence the wine’s taste). The name “Brunello” translates to “little dark one” in Italian, referring to the deep, dark color of the wine.

Brunello di Montalcino is highly regarded for its complex aromas and flavors. It often exhibits notes of red and black fruits, like cherry and plum, along with herbal and earthy undertones. The wine typically undergoes a lengthy aging process, spending several years in oak barrels and then additional time in the bottle. This aging contributes to the wine’s depth, maturity, and ability to age gracefully over many years.

Due to its premium quality and limited production, Brunello di Montalcino is often associated with special occasions and is considered a collector’s item by wine enthusiasts. It pairs well with a variety of Italian dishes, especially those featuring rich flavors like roasted meats, game, and aged cheeses.

Giacomo at the winery “il Cocco” will show his grounds and cellar. You will love tasting Brunello at Il Cocco!

Tiramisu is a popular Italian dessert that combines layers of rich flavors and textures to create a delectable treat.

It typically consists of several key components:

1. **Ladyfinger Biscuits:** These are soft, sponge-like biscuits, also known as Savoiardi, that are dipped in coffee or espresso. They form the base layer of the dessert.

2. **Coffee or Espresso:** Tiramisu gets its distinctive flavor from a soaking of coffee or espresso. The liquid is used to moisten the ladyfinger biscuits, infusing them with a deep coffee taste.

3. **Mascarpone Cream:** This is the creamy and indulgent layer that sits on top of the soaked ladyfingers. It’s made from mascarpone cheese, which is a rich and smooth Italian cheese, mixed with eggs, sugar, and sometimes a touch of liquor like Marsala wine or coffee liqueur. The mascarpone cream is spread over the soaked ladyfingers, creating a luscious layer.

4. **Cocoa Powder:** The dessert is often dusted with a layer of unsweetened cocoa powder, adding a touch of bitterness and balancing out the sweetness of the cream and coffee flavors.

The layers are usually assembled in a dish or serving container, and the dessert is chilled for a few hours to allow the flavors to meld together. The result is a delightful combination of soft and creamy textures with a harmonious interplay of coffee and sweetness. Tiramisu is often garnished with chocolate shavings or grated chocolate for an extra touch of elegance.

The name “tiramisu” actually translates to “pick me up” in Italian, likely referencing the espresso’s caffeine content. This beloved dessert has gained international popularity for its unique blend of flavors and its satisfying, indulgent qualities.

Accommodations with ensuite bathroom

LA VILLA HOTEL – SIENA: Your Tranquil Haven

Day 1, 2 and 3 of our Tuscany guided walking tour welcome you to this inviting haven. Nestled just beyond Siena’s ancient city walls, La Villa is an exquisite “art nouveau” abode from the early 20th century. A short stroll from Siena’s historic heart, it blends timeless elegance with modern convenience. Adorned with tasteful decor that honors its historical essence, this dwelling offers an ideal base to explore the medieval marvels of Siena. With a warm and welcoming staff, expect to feel right at home.

CORSIGNANO HOTEL – PIENZA: Where Beauty Meets Functionality

Discover the allure of Corsignano Hotel in Pienza. Merging beauty with functionality, this newly renovated 4-star gem graces the canvas of Tuscany’s most pristine landscape. Immerse yourself in a world of aesthetic charm and modern convenience. With an exceptional staff and a delectable breakfast spread, your experience here is destined to become a cherished memory of Tuscany’s essence.

2024 Scheduled group tour

• 640 EURO (single supplement only in case you need your double room for single use)

deposit 300 EURO

balance is due 95 days ahead of trip beginning date

you can pay in instalments

2024 Private tour

More guests? Please ask us a quote. We can also tailor the tour to your needs.

if you travel in July or August there is a seasonal surcharge of 400 euro per person

2025 Scheduled group tour

• Do you need your own double room for single use? 390 Euro ONLY!!! single supplement

2025 Private tour

Tuscany has my heart! This was a trip dreams are made of. I have always wanted to see Tuscany but I am not into touristy type trips. I was a little skeptical of this tour but booked it anyway. I was blown away….It exceeded my expectations. Our guides Daniele and Chiara were a JOY to be with. They shared their countryside with us and they shared themselves. Beautiful souls. For me the hiking was wonderful and I would have done more…but beware this is definitely more of a hiking than walking tour. The food was wonderful and the wine amazing! I highly recommend. I can’t wait to try another tour.

The Best Way to See Italy Forget Rick Steves and sign on with Gianni for a wonderful exploration of some of the best Italy has to offer–countryside, history, food, and people. Gianni’s deep knowledge of all these adds so much richness to the experience of walking through picturesque medieval towns and gorgeous rolling hillsides of vineyards, fields and orchards. The accommodations were comfortable and centralized, often with wonderful views. Some of the food will absolutely spoil you for ever eating “Italian” food at home again. And the people we met through farm, winery and other small business visits were perhaps the best of all–passionate about the food they grow and so willing to share their experience. Although this was a tour through the areas surrounding Siena, Montalcino and Pienza, Gianni offers tours in other areas and I would expect the same high level of engagement and effort to provide unique experiences. Truly exceeded my expectations!

Simply the Best! What an amazing and unforgettable experience! Our 8 day walk about Tuscany was like a walk through wonderland. Gianni somehow made each day better than the last. The scenery was magical, the food was incredible and the wine beyond words… Gianni’s vast knowledge and passion is undeniable. He is truly one of a kind as were the places we had the pleasure to visit (wineries, olive oil producer, cheese farm etc.). This is without a doubt the best way to see Italy. We had so much fun!

Walk about Tuscany Loved this tour and would highly encourage others to go. Our guides Gianni and Sara were great, everything ran smoothly from day one. Excellent choices of hotels, restaurants and walking trails. The perfect size group, lots of laughs and good memories. Looking forward to the next one. Grazie, Monica

Under the Tuscan Sun…and a big black cloud but only once I have just returned from 8 fabulous days with Walk About Tuscany hosted by Gianni and Rudy and helped by their hard working transportation crew who ensured we were picked up on time, we traveled safely and no luggage was lost. Congrats to them. I was in a group of 16, coming from many parts of the world and put together by chance. We were treated to a Tuscan experience which will, for me, remain a memory for years to come. We saw everything; from the hill top towns to the wheat fields, from the vineyards to the olive groves, from the churches to the abbeys to the quaint shops and cobblestone streets and each day was a different adventure. We got up close and personal with the Tuscan people, sharing their food, their wines, and learning about their way of life. This was also a walking tour and, boy, did we walk (so sturdy shoes are recommended). It is estimated we covered close to 100 miles, some easy trails, some more challenging climbs. If anyone in the group fell behind or needed time to catch a breath, there was always someone available for company. We were never rushed but there were times we had to be gently reminded that we have a date for lunch or for a wine tasting and we should try not to keep our hosts waiting. We learned so much during each walk; Gianni and Rudy switching back and forth to cover the plantlife and the wildlife not to mention the history of each place we visited. I often wondered…how do these guys know all this stuff!! And in case you think it was all serious business, nothing could be farther from the truth. We had many moments of fun and laughter and even a couple of flute recitals just for a change of pace!! In the end, I have Gianni to thank for this experience. His thoughtful organization and attention to detail were key in delivering a superb product, a memorable adventure and a trip of a lifetime. Walk About Tuscany is highly recommended! Grazie, Gianni

The unforgetable Tuscany I am so amazed with Gianni who operated our tour with his in-depth knowledge of every single steps and buildings around Tuscany. Not to mention his creativeness in every moments of our walks. You will have great lunches and dinners with lots of special-2-thumbs-up wines. We also visit Olive Oil producer and given sampler at which is the best (and fresh) olive oil that I had ever tasted ! The scenery view is very awesome, just like the post card. Highly recommended and wouldn’t mind to do this tour again.

Group Tour of Tuscany Hill Towns with Walk About Tuscany Tours I had a marvelous time on this trip. Our guide, Gianni, provided gorgeous walks and unique experiences with local organic producers of wine, produce, cheese, and olive oil. Definitely experiences I couldn’t have had without his guidance and that helped me to appreciate what makes this region unique. Gianni is knowledgeable and expended every effort to ensure that our trip was memorable and unique. We walked, ate very well, drank wonderful wines and learned a great deal about this region of Tuscany and why it is among the most delightful of all Italy.

Founder, trip organizer and guide at Walk About Italy (with a degree in Geology)

I am 51 years old.  Geology is my background (Ph.D.) but to me life is about more than an academic degree. Music and walking are my passions. I have been a certified guide for nature walks since 1999. After working many years as a guide and also in the back stage of the travel industry for foreign walking tour companies, I earned my Tour Organizer business license, valid in Italy and the rest of the world. Let me organize your vacation to Tuscany and other parts of Italy.

Tours he guides: Tuscany, Amalfi, Sicily, Umbria – Assisi & Le Marche

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A true passion for life (with a degree in ethnology)

Sara is a fully licensed guide, both for nature trails and for the city of Siena. Sara was born in a small village in Chianti area. When I first met her few years ago I was struck by her great personality, enthusiasm and kindness. Her background is in Anthropology.

Tours she guides: Tuscany

Photographing Tuscany (with a degree in yoga teaching)

Farming vegetables, olives, chickens, ducks and pigs (with a degree in natural sciences)

Chiara was  born  in Volterra, a charming  Etruscan town  nearby Pisa. After graduating in  Natural Sciences  in 2001 she has become a nature hiking guide, accompanying guests in Tuscany and pleasing them with lovely pic-nics. In 2015 she decided to start  her own farm  with a  vegetable garden, olive trees, aromatic plants, chickens, ducks and pigs . Now she is a tour leader and a farmer. She will take you around with dirty hands for a good reason!

Making pecorino sheep cheese an art (with a degree in natural sciences)

Daniele was  born and raised in a farmhouse in the Tuscan countryside . Ever since he helped his dad to make an amazing  pecorino  sheep cheese .

He’s got a  Master’s Degree in Natural Sciences  in 2009 and started working as a nature guide around the Indian Ocean and Africa, before coming back to his beloved homeland.

As a passionate  birdwatcher , he always keep an eye on the sky during his walks, sharing the pleasure of exploration and the discovery of new places.

Tours he guides: Tuscany

Walking changed my life!

Erica was born in  San Gimignano  from Italian dad and Scottish mum.

Her background is as Sales Executive in an export company but after 10 years she decided to leave the office, change her life and make a job out of her passions:  walking, nature, art, living outdoor and meeting new people and cultures . Now Erica is a licensed  hiking and city guide  and her aim is to let you love Tuscany as much as she does!

group meets here:

At what time, trip ends here:, useful information on the tour, how to prepare for this trip.

Walking or jogging for 60 minutes 3 times a week for 5 weeks ahead of trip will make your experience more enjoyable. In case you live in a flat area you might also incorporate some steps in your physical activity.

What to bring:

• Walking shoes with good traction (sometimes we might have mud on the trail)
• Hat, Swimming suit, sun cream, water bottle to refill with tap water
• Dinners at Italian restaurants do not require any special dress code. Wear shoes with good traction

An average day of the trip

On a typical day you hike/walk with your guide in the morning for 3 hours, then we stop at a restaurant or farmhouse for lunch (lunch can last 1hour and half). We serve local food and wines as we believe that food plays an important role in the enjoyment of Tuscany. In the afternoon there might be some more walking or town stroll. Around 4.30 or 5pm your guide will take you back to the hotel. Your guides are available from 9am to 5pm on each day. Before dinner you will be able to rest a couple of hours. Dinner will be served in a restaurant in town that you will be able to easily reach on foot. At dinner the guide will not be with you. This is why we planned to have most of the hotels in the town centers and pedestrian areas. And if the hotel is away from the town center we have set up transportation to take you to the next restaurant or activity. Local wine is always included for lunch or dinner. We serve vino della casa (house wine) as the quality of local house wines is very high. Not by chance this part of Tuscany is one of the most famous wine making area in Italy (Chianti Classico, Brunello, Vino Nobile di Montepulciano).

In general, the climate in Tuscany is very mild. Usually summers in Tuscany are hot with little or no rain. July and August are the hottest months (but still nice for walking as there is always a breeze blowing up on the hills). Spring (April and May) and Autumn (October and November) are milder. You can have some drops of rain but not too many. Winter is colder but you still can count on many sunny days.

Month   avg. High     avg. Low

Apr   66 °F (19 °C)    46 °F (8 °C) May  73 °F (23 °C)   54 °F (12 °C) Jun     81 °F (27 °C)   59 °F (15 °C) Sep    81 °F (27 °C)   59 °F (15 °C) Oct     72 °F (22 °C)  52 °F (11 °C) Nov    61 °F (16 °C)  45 °F (7 °C)

Tipping your guides

Single Guide Tour: If your tour is led by a single guide, it is customary to provide a minimum tip of 20 euros per day, per customer. Your guide will be your primary source of information and assistance throughout the tour, and this gesture will reflect your gratitude for their personalized service.

Dual Guide Tour: In cases where your tour is led by two guides, we recommend a minimum tip of 10 euros per day, per customer, for each guide. This ensures that both guides are acknowledged for their contributions to your tour experience.

Tipping your drivers

If you wish to tip your drivers each of you might want to tip them 5 euro per day per driver.

Extra expenses

Snapshots from the tour.

Chianti and pecorino sheep cheese

a good team

classic Tuscany

climbing a Tuscan hill

exploring San Gimginano

fresh cold cuts

fresh herbs from the garden

happy walker

relaxed walk

Relaxing with San Gimignano in the background

Sara explaining medieval art

Sara is very tempted by the bomboloni

Siena Cathedral

Poppies in the spring

truffle on pasta

Tuscan green fields

walking in Pienza

Walking in sunflowers

walking in vineyards

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#1 - Scheduled Group tour?

#2 - private tour, 2022 tours that can be combined with cinque terre off the beaten path experience, cinque terre + tuscan splendors.

TUSCANY Sept 4-11 - CINQUE TERRE Sept 17-23 (6 night gap)

CINQUE TERRE + AMALFI WANDERS

AMALFI COAST Oct 10-16 - CINQUE TERRE Oct 17-23 (1 night gap)

CINQUE TERRE + SICILIAN FLAVORS

CINQUE TERRE Sept 17-23 - SICILY Sept 25- Oct 1 (2 night gap) SICILY Oct 9-15 - 5 TERRE Oct 17-23 (2 night gap)

CINQUE TERRE + UMBRIA, ASSISI & LE MARCHE MARVELS

UMBRIA MARCHE Oct 10-16 - 5 TERRE Oct 17-23 (1 night gap)

2022 TOURS THAT CAN BE COMBINED BACK TO BACK 

COMBO DISCOUNT 150€

The nights of gap are not included. We will provide suggestions for places to visit and stay in between the two tours.

TUSCAN SPLENDORS + AMALFI COAST WONDERS

TUSCANY May 10-17 – AMALFI COAST May 18-24 (1 night gap) TUSCANY Sept 4-11 – AMALFI COAST Sept 12-18 (1 night gap) TUSCANY Oct 2-9 – AMALFI COAST Oct 10-16 (1 night gap) AMALFI COAST Oct 10-16 – TUSCANY Oct 16-23 (no night gap)

TUSCAN SPLENDORS + SICILIAN FLAVORS

TUSCANY Oct 2-9 – SICILY Oct 9-15 (no night gap) SICILY Sept 1-7 – TUSCANY Sept 11-18 (4 night gap) SICILY Sept 25-Oct 1 – TUSCANY Oct 2-9 (1 night gap) SICILY Oct 9-15 – TUSCANY Oct 16-23 (1 night gap)

TUSCAN SPLENDORS + UMBRIA, ASSISI & LE MARCHE MARVELS

UMBRIA MARCHE May 3-9 – TUSCANY May 10-17 (1 night gap) TUSCANY Sept 11-18 – UMBRIA MARCHE Sept 19-25 (1 night gap) TUSCANY Oct 2-9 – UMBRIA MARCHE Oct 10-16 (1 night gap) UMBRIA MARCHE Oct 10-16 – TUSCANY Oct 16-23 (no night gap)

TUSCAN SPLENDORS + CINQUE TERRE OFF THE BEATEN PATH EXPERIENCE

TUSCANY Sept 4-11 – CINQUE TERRE Sept 17-23 (6 night gap)

AMALFI COAST WONDERS + SICILIAN FLAVORS

AMALFI COAST May 18-24 – SICILY May 25-31 (1 night gap) SICILY Sept 1-7 – AMALFI COAST Sept 12-18 (5 night gap)

AMALFI COAST WONDERS + UMBRIA, ASSISI & LE MARCHE MARVELS

AMALFI COAST Sept 12-18 – UMBRIA MARCHE Sept 19-25 (1 night gap)

AMALFI COAST WONDERS + CINQUE TERRE OFF THE BEATEN PATH EXPERIENCE

AMALFI COAST Oct 10-16 – CINQUE TERRE Oct 17-23 (1 night gap)

UMBRIA, ASSISI & LE MARCHE MARVELS + SICILIAN FLAVORS

UMBRIA MARCHE Sept 19-25 – SICILY Sept 25-Oct 1 (no night gap)

CINQUE TERRE OFF THE BEATEN PATH EXPERIENCE + SICILIAN FLAVORS

CINQUE TERRE Sept 17-23 – SICILY Sept 25- Oct 1 (2 night gap)

SICILIAN FLAVORS + CINQUE TERRE OFF THE BEATEN PATH EXPERIENCE

SICILY Oct 9-15 – 5 TERRE Oct 17-23 (2 night gap)

UMBRIA, ASSISI & LE MARCHE MARVELS + CINQUE TERRE OFF THE BEATEN PATH EXPERIENCE

UMBRIA MARCHE Oct 10-16 – 5 TERRE Oct 17-23 (1 night gap)

WALK RATING

Activity level: 2+ (on a scale from 1 to 5) Daily Hours : Up to 3 Daily Distance : 3 to 10 km (2 to 7 miles) Walking Surfaces : Gentle with some uneven terrain Daily Elevation : Up to 200 mt. (650 feet) Personal Fitness: Light exercise weekly, active lifestyle

Activity level: 3 (on a scale from 1 to 5) Daily Hours : Up to 3 Daily Distance : 3 to 10 km (2 to 7 miles) Walking Surfaces : Gentle with some uneven terrain Daily Elevation : Up to 300 mt. (1000 ft.) - Average day 200 mt (650 ft.) Personal Fitness: Light exercise weekly, active lifestyle

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Bosnia and herzegovina, czech republic, liechtenstein, netherlands, north macedonia, switzerland, türkiye/turkey, united kingdom, bike & boat, multi-activity, vessels & boats, advanced search, tuscany walking tours, explore tuscany your way on a picturesque walking holiday.

One of Italy’s most appealing destinations, Tuscany offers visitors a staggering breadth of walking tour experiences. The exquisite landscapes here seem plucked from a master painting, and indeed, it’s in Tuscany that you’ll find some of the country’s finest collections of Renaissance art and architecture.

Explore charming medieval villages such as San Gimignano, discover the rich history and impeccable art heritage of Tuscany’s beautiful cities—Florence, Siena, Pisa and Lucca - then delve into the quieter countryside for ancient monasteries, rolling vineyards and olive groves, castles, villas and medieval walled towns. Fall in love with Tuscany’s rustic farmhouse cuisine, and head to the Chianti wine-growing region for gently rolling landscapes, historic wine cellars and, of course, plenty of the region’s eponymous drop. Ramble through the 'green heart' of Italy from Florence to Rome, or hike the historic Via Francigena, an ancient road and pilgrimage trail stretching more than a thousand kilometres from Canterbury (England) through France, Switzerland and Italy, finishing up in the Eternal City of Rome. Or simply wind your way along scenic back roads through gentle hills and valleys, discovering landscapes so idyllic you’ll immediately know why this region is so popular with painters. Join us as we explore beautiful Tuscany on an unforgettable walking holiday.

Find your trip

Via Degli Dei: Bologna to Florence

Moderate to Challenging

Via Francigena: Best of Tuscany

The Full Via Francigena

Via Francigena: Fidenza to Tuscany

Via Francigena: Pontremoli to Lucca

Via Francigena: Lucca to Siena

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Making Tuscany affordable

Walking trips in Tuscany only include what you need like accommodation, meals, bikes on cycle trips, luggage transfers, maps and route directions on self guided trips and an experienced local guide for group trips, as well as the peace of mind that comes with complete backup and support.

Explore Tuscany at your own pace

On self guided Tuscany walking trips you can expect to receive up-to-date and well researched route notes and maps, seamless luggage transfers and competitive pricing on all essential services. Many self guided trips also have daily departure dates, allowing you to enjoy the convenience and flexibility a self guided trip offers.

Enjoy flexibility and choices

Cycling or walking, 2 star or 4 star, small groups or self guided, land or sea - we can help you explore Tuscany exactly the way you want.

Charming local hotels

In Tuscany, we use a range of 2-3 star hotels, often family run. These charming hotels provide access to local living thanks to your hosts. The hospitality is generous and their local knowledge is invaluable. Where possible, we choose hotel locations that add to your experience.

Agriturismi

These ‘farm stay’ style accommodations are found on independently owned working farms. You can expect fantastic local flavours at meal time from your hosts.

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Tuscany Walking Tour

Pilgrims trail | small group tours italy.

Many of us have already visited well known Tuscan hotspots such as Florence or Pisa. But just as rewarding are the lesser known sights that we take you to on our Tuscany Tours – having lunch in a monastery founded 1000 years ago, walking through the evocative Tuscan countryside and coming across ancient Roman baths.

Being on foot, we have plenty of time to fully appreciate the Tuscan countryside on our Tuscany Walking Tour. A glass of Chianti at the end of the day sourced from the vineyard right outside your door is also not to be missed.

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Tuscany Tour Highlights

• Walk along the pilgrims trail called the Via Francigena , a route leading from Canterbury in England to Rome - developed in the 10th century
• Spend time in San Gimignano, Siena, and our favourite, Monteriggioni – a picturesque village still contained within the medieval walls
• As we walk, the Tuscan countryside begins to reveal countless interesting sights, whether it be an Etruscan tomb, the abundant wild flowers, or deer emerging at dusk
• Enjoy a range of local Italian food along the way - on this Tuscany walk you work up an appetite and we restore your energy Tuscan-style; the delicious panforte or ricciarelli at a range of carefully selected restaurants

Tuscany walking tour- Pilgrims Trail

• The Tuscany tour traverses the Tuscan countryside from Siena to Gambassi Terme - there are five days of walking
• The walks are fully guided (no need to spend frustrating hours looking for the path!) and we organise for your luggage to be transported to our next destination each day
• This walking tour is a balance between the more active side – the walks – along with enjoying the Italian cuisine, and visiting a range of interesting places
• We stay in a range of characteristic Tuscan accommodation, including a farmhouse established in the 12th century, and a hotel based in a medieval palazzo in San Gimignano
• Small Group Tours - maximum 14 people
• This is the Tuscany trip that you’d design for yourself. We are Italy... with pleasure
• Our 7 day Tuscany tour starts in Siena and finishes in Florence

What our customers say about Italy With Pleasure

Accommodation.

We have an interesting combination of accommodation as we move through the Tuscan countryside.

Starting in Siena we stay at the Hotel Duomo, very central with all the attractions of this wonderful city easily accessible on foot.

For our first night on the trail we stay at Borgo Galliano, a rural lodge, beautifully presented in amongst fields and oak trees.

Moving on, we stay at the Tenuta Mensanello, a collection of old stone buildings set amongst a working farm. You can enjoy their homegrown food and wine at their excellent restaurant.

Our next stop is the town of San Gimignano, where we stay at the Hotel Antico Pozzo. You’ll love the Tuscan style of this establishment, set right in the heart of San Gimignano.

For our final night we stay at the Tenuta Sant’Ilario, a boutique hotel where you can celebrate the finish of your walk with a swim, followed by some top cuisine in their restaurant.

Day 1:  Buongiorno Siena!

We meet in Siena in the afternoon, in our hotel that is right in amongst the historic centre of Siena.

Before any thoughts of walking we head to a café for some of Siena’s renowned foods such as ricciarelli and cantucci.

For those that haven’t seen Siena, we take a walk together to the cathedral, where you discover some interesting quirks of its construction and history. And looking around our part of town you’ll see how loyal the locals are to their zone – the area that they represent in the palio, the bareback horse race around the central piazza.

In the evening we walk through the centre of Siena – through the Piazza del Campo, tonight full of people enjoying their evening aperitivo rather than racing horses.

We have dinner together in a trattoria where we enjoy the local cuisine – this week, while primarily about walking – is also a chance for us to enjoy a progressive discovery of the local cuisine.

WALKING DETAILS:

This walk is fully guided, total distance: 11 miles / 18 km, meals included: dinner, accommodation: hotel duomo, day 2: into the tuscan countryside.

Today we set off on the first section of our walk (and we start to appreciate that our luggage is being transported for us; we only need to carry what we need for the day).

As we make our way out of Siena we come across many examples of how this city lived and fought in the centuries past. History is all around us, we explain to you what you are seeing and the significance of Siena to the region.

The trail that we are following this week, the Via Francigena passes right through Siena.

We reach the outskirts and the verdant countryside that will be our environs for the week. We follow the route and soon reach the first ‘strada bianca’ (‘white road’). These are the more peaceful rural trails that we will follow for the next few days, small white gravel roads and paths that are typical of the Via Francigena in Tuscany, many of these paths have been upgraded in recent years making for an excellent walking route.

Through the morning we find our rhythm as a walking group – we have planned the days to include time to stop and look at anything of interest along the way, our days aren’t a race to the finish but rather a gradual exploration of the territory.

We stop for lunch at a small rustic eatery right on the trail – here you’ll get your first feeling for the Tuscan hospitality.

As you adjust to the pace and rhythm of the walk you start to pick up on the smaller details and the more subtle changes through the day. The way people live here, with their family olive groves and well tended gardens. The small scale farms that are the foundation of this region. The beauty of the Tuscan countryside. The 16th century castle Chiocciola that we pass today.

This is the aim of our tour - to give you time to appreciate your environment, to fully explore the cuisine, as well as seeing the numerous historic sites every day on our trail.

Mid afternoon we reach our accommodation for the night, Borgo Galliano. This is an ‘agriturismo’, a country lodge.

We take a break for a few hours to put our feet up and reenergise before meeting for dinner. We enjoy a meal in the restaurant of our lodge.

Accommodation: Borgo Galliano

Day 3 - monteriggioni to colle di val d’elsa.

Departing from Borgo Galliano (and wishing we could stay more than just one night!), a short walk takes us to the town of Monteriggioni. This village has a medieval feel, and is still entirely contained within the 13th century walls, just as it was centuries ago when Siena and Florence were rival city states.

The small piazza and old stone buildings is simply charming. We allow an hour or two for you enjoy being in Monteriggioni, time to look around the central village. Monteriggioni is a rare example of a town still contained within the original medieval walls. You’ll notice numerous references to the Via Francigena here as Monteriggioni is a well known stop on the route – in fact it is unmissable. Mid morning we exit the town walls at the Porta di Ponente gate - the route of the Via Francigena.

We walk for just long enough for you to work off your morning gelato before coming to our lunch stop. The restaurant is contained within a 12th century monastery complex, the Monastery of San Salvatore. Originally this would house pilgrims en route to Rome. We dine in a courtyard that has seen many centuries of monks walk its paving stones.

We follow the trail in the afternoon over the gently rolling hills. The vineyards we pass through in this part of Tuscany are part of the Chianti wine zone, and they promise us a welcome reward at the end of the day just as they did for the pilgrim Sigeric in the year 990, when he documented the route that we follow this week. Sigeric was the Archbishop of Canterbury, travelling to Rome to meet the pope. His notes from that journey are an early reference to this pilgrim’s trail.

We stop in to look at some ancient Etruscan (and later Roman) baths at Caldone.

We reach the Tenuta di Mensanello, a boutique hotel based in a small hamlet. There’s time for a swim in their pool, a look around their gardens, before finding those rewards awaiting a weary pilgrim in the evening - they make their own wine and grow much of their own produce, this is farm to table at its best.

Total distance: 9 miles / 15 km

Meals included: breakfast, lunch accommodation: tenuta di mensanello, day 4 - colle di val d’elsa to san gimignano.

We set out from our destination today, continuing north towards the town of San Gimignano. En route we find a number of interesting features, such as the Romanesque church of Santa Maria a Coneo. We also have a special chance to see the site of an Etruscan necropolis (cemetery), the population that lived in Tuscany before the Romans.

Today you meet the locals for lunch, in a small inn. Soon we start to see the medieval towers of San Gimignano, erected by the noble families in a bid to out do each other.

San Gimignano is one of Italy’s most well-preserved medieval towns. Perched on a hilltop with numerous medieval towers, it is a commanding presence dominating the patchwork of olives and vineyards in the valley below. San Gimignano’s narrow streets boast many craftsmens’ workshops. And there’s a particularly good gelateria in the piazza.

We reach our hotel for the next two nights, the Hotel Antico Pozzo. This hotel is right in the historic centre of town, nestled in the evocative lanes. From here you can wander into the piazza and watch the world go by.

Total distance: 12 miles / 20 km

Meals included: breakfast, lunch accommodation: hotel antico pozzo, san gimignano, day 5: san gimignano wine country.

For today’s walk we do an excursion from San Gimignano, returning in the afternoon to our base. Our walk today, a diversion from the Via Francigena, is through the renowned vineyard area of San Gimignano.

This is a scenic walk following a route that gets us up close to the vines that form such a key element of the Tuscan landscape. The key wine made here is vernaccia, a white wine with a long history – it was first recorded here in 1276. It still tastes good in the present too, we enjoy some of the local product over lunch.

This excursion returns to our departure point in San Gimignano.

As we stay another night here in San Gimignano, anyone who wishes to rest their legs can skip the walk - simply stay put and soak up the atmosphere of the town. There is plenty to see here and your more relaxed day will allow you to enjoy our next walk tomorrow. Or simply find a good spot in the piazza with a glass of local vernaccia and watch the world go by.

Total distance: 10 miles / 15 km

Day 6: our final destination, gambassi terme.

Today you walk along one of the more scenic areas in Tuscany, and it is our last leg of our journey. We make our way thought the classic Tuscan countryside, stopping when there are interesting sights to see, such as the Sanctuary at Pancole with its fascinating back story.

Walking through this countryside you can see how some aspects of life here follow the seasonal cycles of planting and harvest, as they have done for many generations.

We reach our destination – the boutique hotel Tenuta di Sant’ Ilaria, which is actually on the intersection with another ancient route, the Salt Road.

Our accommodation is entwined with this history, the oldest part of the complex where we stay, was built in the 12th century.

Total distance: 8.5 miles / 14 km

Meals included: breakfast, lunch, dinner accommodation: tenuta sant’ ilario, day 7: arrivederci tuscany.

Today is our last day, we travel back to Florence and bid you “buon viaggio”. The tour finishes in Florence at 11:30 a.m.

Meals included: Breakfast

Tuscany Pilgrims Trail Walking Tour Dates:

This tour is run on request for groups of six or more.

Tour Price: €2500

* Prices listed are based on twin share * Single supplements of €300 for solo travellers

Tour Price Includes:

• All accommodation
• Meals as listed in the itinerary: breakfast every morning, plus a main meal each day
• All costs/entry fees for activities listed in the itinerary
• All transport during the tour. Travel is in our van/minibus with a professional driver
• Daily luggage transfers
• 'Italy With Pleasure' provides a tour manager for the duration of the trip

Tuscany Map

• Northern Territory
• New South Wales
• South Australia
• Western Australia
• Private Groups
• NEW FlexiWalk
• New Zealand
• United Kingdom
• Camino Walks Europe
• Tasmania Self Guided
• NSW Self Guided
• Victoria Self Guided
• South Australia Self Guided

Booking Terms and Conditions

• Eco Tourism
• Frequent Walker Program
• Equipment & Gear Hire
• Customer Testimonials
• Gift Vouchers
• Accessibility
• The Bloody Long Walk

7 day Walk Tuscany’s Via Francigena, Italy

A pack free guided 7-day highlights walk.

Embark on a truly spectacular walking journey along the historic ‘Camino to Rome,’ also known as the Via Francigena, and immerse yourself in a sensory feast for the senses. This remarkable adventure traces the footsteps of pilgrims who, for centuries, traversed the path from England to the sacred city of Rome. Our focus lies on the most breathtaking stretch through Tuscany, leading us from the captivating walled city of Lucca to the enchanting town of Viterbo near Siena, Italy.

But this journey is more than just a walking tour. It is a complete immersion into the flavours and traditions that make this region famous. Indulge in unforgettable culinary experiences, relishing in the delectable food and renowned wines that Tuscany has to offer. Luxuriate in superb accommodation including a castle, participate in a hands-on Tuscan cooking class, engage in the excitement of truffle hunting, and delight in wine tastings that will leave your palate craving for more. As you traverse the picturesque landscapes, you’ll be captivated by the rolling hills of vineyards, enchanting woodlands, and protected nature reserves that grace your path. Discover the allure of charming hilltop villages and explore the rich history of magnificent World Heritage towns such as Lucca, with its well-preserved walls, the iconic medieval towers of San Gimignano, and the splendid beauty of Siena. This is truly a journey of a lifetime, where every step reveals new wonders, every taste ignites your senses, and every moment leaves an indelible mark on your soul. Join us on this remarkable adventure along the Via Francigena through Tuscany and create memories that will forever resonate within you.

Each day is flexible allowing our guests to opt-out of any day’s walking and travel with our host guide to explore the local towns.

• Tour Itinerary
• Departure Dates

A Pack Free Walk

Carry as little as your water, camera and lunch

This walk is designed as a Pack Free walking allowing our guests to enjoy the landscapes they walk, without the burden of carrying a heavy pack. After all, walks should be enjoyed not endured. Each day our guests will walk with a small day pack big enough to carry your lunch, water and camera and your bags will be transported to your accommodation each day.

Wow-amazing Inclusions

Winery visits, cooking classes, truffle hunting and more

This tour offers more than just walking; it has been meticulously designed to enhance your journey through Italy. In addition to walks, you will have the opportunity to indulge in various enriching experiences. Guests will enjoy a visit to a charming local winery, engage in truffle hunting adventures, and savour the delights of an authentic Italian cooking class followed by a delectable dinner in a locals home.

Fabulous meals featuring local wines

and regional specialities

Dinner together will be a highlight of our tour. Indulge in the culinary delights of Italy as you savour fabulous Italian wine and delectable cuisine throughout your tour, immersing yourself in a gastronomic journey that showcases the country’s rich flavors and traditions. From exquisite Tuscan wines to mouthwatering pasta dishes and authentic regional specialties, every meal becomes a celebration of Italy’s vibrant food culture.

Flexible walking

Choose a shorter walk or take the day off and explore the towns

Our tours are thoughtfully crafted to provide flexibility in walking options. Each day, you have the choice to embark on the main walking itineary, a shorter walk or opt out of walking and enjoy extra time for a leisurely exploration of the charming local towns, allowing you to customize your experience based on your preferences and energy levels.

Tuscanian Hotel Lucca or similar

Nestled within the enchanting city of Lucca, we stay at the charming 4-star Tuscanian hotel which resides in the very heart of this historic destination. With a delightful blend of exceptional services, welcoming staff, and refined accommodations, we ensure a memorable stay for our guests. Situated in a serene locale, our elegant hotel occupies a historic 17th-century building. Spanning three floors, it gracefully overlooks a tranquil inner courtyard and one of Lucca’s bustling main streets.

Villa Petriolo or similar

Experience the epitome of luxury at Villa Petriolo, an enchanting Italian villa nestled in the rolling hills of Cerreto Guidi. Spanning over 160 hectares, this grand estate offers a breathtaking panorama that stretches as far as the eye can see. Indulge your senses in the culinary delights of Villa Petriolo’s remarkable restaurants, where skilled chefs meticulously craft exquisite dishes. After a day of exploration, unwind and rejuvenate by taking a refreshing dip in the inviting pool, perfectly situated amidst the stunning scenery.

Hotel La Collegiata, San Gimignano or similar

Hotel La Collegiata, originally a Franciscan convent constructed in 1587, is situated on the outskirts of San Gimignano. Immerse yourself in the ambiance of the Sienese Renaissance as you step into the rooms, adorned with furnishings that reflect the grandeur of the era’s palaces. Unwind and rejuvenate during a leisurely afternoon at the hotel’s expansive pool.  Hotel La Collegiata provides an enchanting experience where guests can bask in the beauty of the past while enjoying modern comforts and amenities.

Borgi San Luigi or similar

Borgo San Luigi offers a truly bespoke experience, perfectly tailored to your needs. This expansive oasis spans across 60,000 square meters, providing ample space and hidden nooks to nourish your soul. Indulge in the pleasure of sipping exquisite beverages by our semi-Olympic swimming pool, meander through the enchanting woods that envelop the estate, or enjoy a game of tennis on our private court.

Palazzo Borghesi Residenza d'Epoca or smiliar

Siena, Italy

Nestled in the heart of Siena’s historic center, Residenza d’Epoca Palazzo Borghesi is surrounded by a captivating tapestry of palaces, churches, museums, and remarkable monuments. This extraordinary location immerses guests in the rich heritage and cultural treasures of the city. Each of its six elegant rooms, exudes its own unique character and charm. Within these elegant spaces, the blend of sophistication and allure is enhanced by the magnificent 5-meter vaulted ceilings adorned with enchanting frescoes.

Feature Castle Stay at Castello di Velona Resort

Perched majestically atop a hill, Castello di Velona Resort, Thermal Spa & Winery is a captivating historical property. Originally a fortified fortress dating back to the 11th century, this magnificent structure has been meticulously renovated to offer a unique and luxurious experience. Nestled in the picturesque region of Tuscany, the castle commands panoramic views of the entire Val d’Orcia with endless rows of olive trees and vineyards.

Superb Local Guide and Australian Guide

Delivering a world-class tour

Guides are essential in delivering the ultimate walking experience. You’ll be accompanied by a local guide who has a passion and enthusiasm for the area and a second host guide, one of our experienced Senior Guides from Australia who will accompany you for the entire trip ensuring we deliver a world-class walk up to our high standards.

Personalised Tours

Our tours offer an intimate and personalized experience, ensuring small group sizes with a maximum of 12 people. If you have a larger group, please reach out to us for further information and arrangements tailored to your specific needs.

To find out more click on any of the below links:

Why choose us.

Your 7 day walking holiday includes:

• Pack Free fully supported walk with no heavy packs to carry
• 1 night accommodation at The Tuscanian Hotel, Lucca or similar
• 1 night accommodation at Villa Petriolo, Fucechio or similar
• 1 night accommodation at La Collegiata, San Gimignano or similar
• 1 night accommodation at Borgo San Luigi, Isola or similar
• 1 night accommodation at Palazzo Borghesi Residenza d’Epoca, Siena or similar
• 1 night accommodation at Castello di Velona Resort or similar
• Cooking Class in the home of a local
• Truffle Hunting and lunch
• Wine tasting
• 7 x delicious lunches
• 6 x superb dinners every evening featuring local produce
• Complimentary wines with evening meals
• 6 x breakfasts
• Professional and passionate guides (1 local and 1 from Australia)
• Transfer from Florence to the start of the walk
• Luggage transported to your accommodation each day
• Flexible walking options or sightseeing each day

• Walk 13kms. Hours 3.5 hours.  Ascent 200m. Descent 200m

Guests will need to organise their own flights to Italy the day prior to the tour. 

SUGGESTED PRE-TOUR ACCOMMODATION: Hotel Cerretani Florence- M Gallery Collection

• Walk 13kms. Hours 3.5 hours.  Ascent 200m. Descent 200m. Optional shorter walks available.

Meet our representative in Florence at 7.30am in the foyer of the Hotel Cerretani Florence- M Gallery Collection from here we transfer (35 mins drive) to Valpromaro where our walk to Lucca begins. Our journeys starts in the small village of Valpromaro in the foothills of the Apennine Mountains. Walk through quite woodlands towards the picturesque village of Piazzano. We eventually make our way along the banks of the river Serchio into Lucca, a well-preserved Renaissance walls that circle the city. It’s hard not to fall in love with Lucca with its medieval cityscape of impressive square and narrow charming cobblestone streets. This charming historic city is known as the the city of a hundred churches as well as the home of ceramics due to its many pottery shops. We make our way to our accommodation for the night at the Tuscanian Hotel or smilar a charming 4 star hotel built in the 17 th century in the heart of the city. Enjoy the afternoon to relax and wander around Lucca at your own pace, visit the city ramparts of explore the Piazza dell’Anfiteatro, the site of an ancient Roman amphitheatre. In the early evening immerse yourself in a charming cooking class in a local home, where the warm and inviting atmosphere sets the stage for a memorable experience. Donning an apron, you’ll engage in hands-on preparation of authentic Tuscan pasta, guided by the charming Silvia who will share her knowledge and techniques. Once the cooking is complete, sit down with your fellow passengers to savour the fruits of your labour. The laughter and joy that fill the table will create lasting memories of your Tuscan cooking class in Lucca.

• Walk 14kms. Hours 3.5 hours. Ascent 100m. Descent 100m

Walk 14kms. Hours 3.5 hours.   Ascent 100m. Descent 100m. Optional shorter walks available.

After breakfast we by-pass the walk’s surburban roads on a short 20 minute transfer to Altopascio. The walled village of Altopascio which looks like a fortress was founded in the 11th Century and was once the home of the Knights of Tau that offered refuge for weary travellers. It offers a charming place to start our adventure as we walk through the town admiring the architecture before venturing into open countryside. You’ll pass through quaint villages and hamlets, where time seems to stand still. Take the opportunity to greet friendly locals, who may be tending to their gardens or enjoying a leisurely chat in the shade. The path continues though the Cerbaie Woods walking though enchanting forests of Oaks, Firs and Alders. Arriving in Fucecchio, you’ll find a town steeped in history and culture. Take a moment to explore the narrow alleys, uncovering hidden corners and admiring the architectural wonders of the past. The atmosphere is filled with a sense of tranquility and authenticity, allowing you to fully appreciate the beauty of this Tuscan gem. Enjoy lunch at a local café in the town before transferring to our accommodation at the stunning Villa Petriolo or similar overlooking hills of scenic vineyards. Enjoy some downtime taking in the tranquil oasis of the villa before embarking on a captivating truffle hunting adventure in the enchanting woodland near San Minato, known for its hidden treasures. Accompanied by experienced truffle hunters traverse the forest trails, inhaling the earthy scents that waft through the air. Learn about the different types of truffles, their seasonality, and the techniques used to locate them. After a successful hunt, revel in the satisfaction of your discovery and enjoy a well-deserved tasting session, where you’ll savour the complex flavours and intoxicating aromas of these prized delicacies. We return to our accommodation where you can immerse yourself in the crystal-clear waters of the villa’s inviting pool. Indulge in a delectable dinner served with the finest local wines, perfectly complementing the flavours of Tuscany.

• Walk 13.4kms. Hours 3.5 hours. Medium. Ascent 350. Descent 350m

Walk 13.4kms. Hours 3.5 hours. Medium. Ascent 350. Descent 350m. Optional shorter walks available.

We enjoy breakfast before farewelling the charming Villa Petriolo, as we head to Gambassi to start our walk (45 mins). Today’s walk is rated as one of the most beautiful as it takes us from Gambassi Terme to the magnificent hilltop town of San Gimignano. Gambassi Terme is a town known for its thermal baths and picturesque surrounds. The approximately 13.4-kilometres journey takes you along peaceful country roads and winding paths, offering breathtaking views of vineyards, olive groves, and rolling hills. As you walk, take in the fragrant scents of the Tuscan landscape and listen to the harmonious sounds of nature. Approaching San Gimignano, you’ll be enchanted by the town’s distinctive skyline, dominated by its medieval towers. The UNESCO World Heritage Site boasts an impressive collection of ancient towers, providing a glimpse into its storied past. As you enter the town, you’ll pass through the old city walls and step into a world frozen in time. Wander through San Gimignano’s charming streets, lined with well-preserved medieval buildings, artisan workshops before stopping for lunch in the town. The remainder of the afternoon is yours to wander through the streets of San Gimingnano or head to the hotel for a swim and relaxation. Our accommodation this evening is a tthe magnficinet La Collegiata with sweeping views of the surround valley and of the towers of San Gimignano. Tonight we will dine in a local restaurant in the heart of San Gimignano enjoying a wonderful dinner served with local wines.

• Walk 16kms. Hours 4 hours. Medium. Ascent 100m. Descent 100m

Walk 16kms. Hours 4 hours. Medium. Ascent 100m. Descent 100m. Optional shorter walks available.

After bidding farewell to San Gimignano, we relish a delightful breakfast at our hotel before embarking on our journey to Badia A Coneo. This picturesque village welcomes us with its enchanting 12th Century Benedictine Abbey, nestled amidst rolling hills and vineyards. The trail beckons, guiding us through expansive stretches of woodland and open ridges adorned with olive groves. Along the way, we encounter charming hamlets, rustic farmhouses, and ancient stone walls. Pausing for a moment, we indulge in the breathtaking panoramic vistas of the Tuscan countryside, where fields and distant hilltop villages create a captivating patchwork. Continuing our walk, we gradually approach the hidden gem of Abbadia a Isola. Founded in the year 1000, this village flourished around the magnificent structure built on a strip of land rising from the lake. As we draw nearer, the architectural splendour and serene ambiance of Abbadia a Isola captivate our senses. We make our way to the impressive Monteriggioni Castle situated grandly on the top of a hill. Visiting Monteriggioni Castle in Italy is like stepping into a medieval masterpiece, you’ll be captivated by its well-preserved architectural marvels, including the impressive ramparts and battlements that offer breathtaking vistas of the surrounding Tuscan countryside. Afterwards we visit a local vineyard, our visit begins in the vineyards see the grapes up close, afterwards we savour a selction of wines accompanied with cured meats and cheeses. Later we head to our accommodation at the delightful Borgo San Luigi. Tonight savour a delectable dinner accompanied by exquisite Italian wines at our charming hotel.

• Walk 18.9kms or shorter 12km option available. Hours 5.5 hours. Medium. Ascent 300m. Descent 300m

Begin your day with a delightful breakfast at the hotel, preparing for an enchanting walk from Monteriggioni to the captivating town of Siena. As you set off, be prepared to be mesmerized by the breathtaking Sienese countryside, adorned with charming hamlets and majestic castles that dot the landscape. Immerse yourself in the serenity of wooded areas embellished with holly, oak, and olive trees, creating a tranquil ambiance. If you prefer a shorter walk, you have the option to walk with the group until lunchtime, and then you’ll be dropped off in Siena to explore this captivating city. For those opting for the longer walk, continue your journey directly into Siena, relishing the scenic route and embracing the charm of the charming villages and rural vistas along the way. Upon arrival in Siena, you’ll be greeted by the awe-inspiring Gothic architecture, narrow cobblestone streets, and vibrant piazzas that bring the city to life. Take advantage of the free time to explore the city’s hidden corners, visit iconic landmarks, and soak up the rich cultural heritage. Tonight we stay at Palazzo Borghesi Residenza d’Epoca or similar.

Later in the evening, indulge your taste buds with a delectable dinner, expertly paired with exquisite Italian wines, all within the warm and inviting ambiance of our charming hotel. Reflect on the day’s memorable journey, surrounded by the beauty and allure of Siena’s architectural wonders.

• Walk 10kms. 3.5 Hours. Medium. Ascent 50m. Descent 50m

After breakfast farewell Siena and embark on a scenic walk from Isola d’Arbia to Ponte d’Arbia, immersing yourself in the natural beauty of the Tuscan countryside. This section of the trail is very particular picturesque with lots of photo opportunities and unlimited views. As you begin your journey, the rolling hills and vineyards create a picturesque backdrop, offering a serene and peaceful atmosphere. The path leads you through charming rural landscapes, dotted with charming farmhouses and fields of golden wheat swaying in the gentle breeze. Along the way, you’ll cross quaint stone bridges over babbling streams, adding to the idyllic ambiance. As you approach Ponte d’Arbia, the charming village greets you with its rustic charm and historic character. Take a moment to explore the village, perhaps visiting the medieval bridge that gives it its name. Afterwards we travel to our accommodation for the night the superb Castello di Velona Resort . This spectacular castle hotel is set high on the hill with spectacular views over the valley of vineyards and groves below. Dine in the restaurant enjoy a gourmet dinner accompanied by wines grown on the grounds

• Walk 18.3kms. 5.5 Hours or shorter walk 12kms – 3 hours. Medium. Ascent 150m. Descent 460m

Following a satisfying breakfast, we bid farewell to the enchanting castle hotel and begin our journey towards Montefiascone. Embark on an exciting walk today that guides you across a vast plain, creating a natural divide between the serene Lake Bolsena and the majestic Cimini Mountains. As you traverse this captivating landscape, you’ll find yourself immersed in the beauty of flourishing vineyards, elegant cypress trees, and picturesque olive groves, each contributing to the enchanting scenery that accompanies your journey towards Viterbo. Along the way, take a well-deserved break at Bagnaccio, a historical site where pilgrims of old would pause to indulge in the rejuvenating ancient thermal baths. Don’t forget to pack your swimming suit, as you’ll have the opportunity to immerse yourself in the steamy thermal pools, formed by the natural volcanic hot spring. Remarkably, these thermal baths have retained their allure for over two millennia, offering a glimpse into the bathing rituals of the Romans. After a rejuvenating interlude, continue your exploration towards Viterbo, a walled city of great historical significance. Originally founded by the Etruscans and later embraced by the Romans, Viterbo is one of the prominent towns in Lazio. Take time to wander through the narrow streets of its captivating historic quarter, where every corner reveals traces of the city’s storied past including the ‘Palazzo dei Papi’, also known as the Papal Palace, an architectural gem that stands as a testament to Viterbo’s rich heritage.

Tour Availability

Each year we will run a few tours in the cooler months of late April and September  We will also consider opening up a new departure date if we have enough demand. Email us at [email protected]

2024 DATES ARE:

• 28 April 2024
• 21 September 2024

(Please note if you are booking 3 months or less before departure – we will need to confirm accommodation with our suppliers is still available and an alternative of similar standard may be offered instead).

PRIVATE GROUPS: Date of your choice is available for groups of 10 people or more. Subject to availability. Please contact us for more details on (02) 9975 4553 or email:  [email protected]

________________________________

INTERNATIONAL FLIGHTS: Please note your tour price does not include flights to / from the countries visited.  We are offering our clients a service to book their international flights and any other travel plans during their holiday. If you would like our Flights Specialist to organise these requirements, please email us at [email protected] with your requirements.

Tour Prices

HURRY OFFER ENDS UNTIL SOLD OUT - LIMITED SPOTS AVAILABLE! Spot Special saving of up to $500 per couple or $250 per person available on specific departures when you pay in full at time of booking. ________________________________

PRIVATE GROUPS Private groups of 10 - 12 people can choose the date of their choice. Subject to availability. ________________________________

INTERNATIONAL FLIGHTS Please note your tour price does not include flights to / from the countries visited.  We are offering our clients a service to book their international flights and any other travel plans during their holiday. If you would like our Flights Specialist to organise these requirements please email us at [email protected] with your requirements.

Discount Information

PAST PASSENGER DISCOUNT: Those who have travelled with Life’s An Adventure previously, receive a past passenger discount of $100. This discount will automatically be deducted from future bookings when you book online using the same email address used for past bookings.

EARLYBIRD CANCELLATIONS: Cancellations are not permitted for Earlybird Deals or Spot Specials, however, transfers to another date are permitted 12 weeks or more prior to departure. We advise taking out travel insurance, in case unexpected circumstances prior to the trip, prevent you from joining this tour. Early bird or Spot Special discounts cannot be used in conjunction with another offer. To receive these special discounts, full payment must be made at the time of initial booking.

• Travel Insurance

Travel Insurance is compulsory for overseas holidays and must be taken out. It will cover items such as cancellation of tour due to minimum numbers not met, or adverse weather conditions, injury, evacuation, delayed flights, illness, etc. We have organised through NIB Insurance for you to purchase travel insurance directly with them – please click here for details. Please note this insurance is only available for Australian Residents, other clients will need to source their own travel insurance.

Additional Information

• Prices are per person in Australian dollars and include GST.
• A deposit of $500 per person is required to secure your booking. (unless taking advantage of Earlybird or Spot Specials in which full payment is required at time of booking).
• Note: If you are booking within 90 days of your departure date – we will require full payment at the time of booking
• Prices are based on twin share of rooms. If you are travelling solo you may be required to share with someone of the same gender. If this is not suitable you can request to pay a single supplement, however, limited single rooms are available per trip so are on a request basis.
• Payments must be made online via our NAB (National Australia Bank) secure payment page via credit card (Visa or Mastercard) or over the phone.
• We advise taking our Travel Insurance to cover items such as cancellation of tour due to minimum numbers not met, or adverse weather conditions, injury, evacuation, delayed flights, illness, etc.

Before you book please read our Booking Terms and Conditions.  Click here

Cancellation Policy and Conditions of Travel

Click here to view Cancellation Policy and Conditions of Travel .

Book Online

• Guided Australian Walks
• Self-Guided Walks
• World Walks
• Booking Terms & Conditions
• Address: HEAD OFFICE: Shop 7, 1306 Pittwater Road Narrabeen NSW 2101. WALKING THE THREE CAPES : Guests can meet this tour at our Life’s An Adventure Premises: 29/6955 Arthur Highway, Port Arthur.
• Phone: (02) 9975 4553 After Hours: 0457 002 482
• Email: [email protected]
• Monday - Friday: 9:00 am - 5:00 pm Saturday - Sunday: Closed

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• Amalfi Coast
• One-Day Guided Tour of Pitigliano
• Five-Day Guided Tour of the Island of Elba

Six-Day Guided Tour of Southern Tuscany

• Your Guides

We are WalkItaly Tours

WalkItaly Tours offers guided walking tours of Italy for both mixed groups and private groups, as well as self-guided walking tours. Our tours of Campania (Amalfi Coast and Capri), Lazio, Tuscany and Sardinia combine walking on off-road paths, learning about local cultural heritage and tasting local foods.

Why these three ingredients? Italy has the highest biodiversity index and highest number of UNESCO cultural sites in the world, and – of course – it has an extraordinary variety of food and wine.

Our tour groups are kept small and are always led by WalkItalyTours staff and local guides, so you’ll be in expert hands while enjoying spectacular scenery, admiring cultural treasures or savouring local delicacies.

Memories of discovering Sagrantino wine, the frescoes at Orvieto, the Ogliastra Sea, and the mussels in Niedditas will come back to you long after your return!

WalkItaly Tours also offers rowing experiences in Rome.

WalkItaly Tours featured in The Guardian

read the article here >

Self-Guided Walking Tours

You don’t have to be a US Navy Seal to join our self-guided tours! Combining adventure with safety, WalkItalyTours provides four levels of support: a good old-fashioned face-to-face meeting before your departure; a road book with an original description and a brief history of the places to visit enroute; GPX files of the itineraries (despite the hi-tech name, these files are easy to use); a WalkItaly team member who can provide 24-hour on-the-spot assistance.

Find out more about our self-guided walking tours of Italy >

Guided walking tours in tuscany.

Our walking tours in Tuscany take inspiration from the guidebook The Cities and Cemeteries of Etruria written in 1842 by George Dennis. Dennis was a typical British explorer who took detailed notes and drawings, many of which are still used as reference in the study of Etruscan culture.

Six-Day tour of Tuscany: Following Etruscan Paths to Giglio Island

One-day guided tour: pitigliano and the etruscan paths >, off-peak trekking along the amalfi coast and capri.

The tour takes in stretches of coastline reaching from Positano to Vietri sul Mare along the Tyrrhenian coast of southern Italy, offering spectacular views of the Gulf of Salerno and Capri Island, one of the most sought-after destinations among travellers who participated in the Grand Tour .

Our walking tours of the Amalfi Coast and Capri >

Walking tours in sardinia.

This land resembles no other place. Sardinia is something else. Enchanting spaces and distances to travel – nothing finished, nothing definitive. It is like freedom itself. D. H. Lawrence Sea and Sardinia

Sardinia is the calmer alternative to a holiday in mainland Italy. You still have it all – sand and sea, restaurants and bars, passeggiate in historic towns – except the sand is very white, the sea very emerald and the small scale means everything is closer to hand and more relaxed. And because this is an island smack in the middle of the Mediterranean, its coastline offers plenty of sumptuous beaches, enticing coves and stretches of water where you can swim (or float) to your heart’s content.

Our walking tours in Sardinia >

Rowing in rome: single session or 5-day rowing experience.

Rowers visiting Rome should try the urban stretch of the river from Ponte Milvio up to the Isola Tiberina. You’ll see Rome from water level – rather than from the road. As well as single sessions we offer a 5-day Rowing training experience in downtown Rome with a certified coach of the Italian Rowing Federation, video review, yoga and biking tour.

Rowing in Rome >

Walkitaly tours, a partner in the off the beaten tracks: walking and biking tours in rome project, was awarded a european commission grant by the cosme programme..

Testimonials

Our Self-guided Tour of Southern Tuscany

Throughout the trip the drivers and luggage handlers were prompt and efficient. The service at all accommodations stops was excellent. The room in Pitigliano was particularly good as it was right in the middle of the town and close to the Jewish quarter. Both of our guides were knowledgeable and the tours they ran were fun and informative. The scenery and history throughout were unforgettable.

Roberto was helpful and efficient and made sure we were fully informed and safe throughout the walk.

This is a great adventure the whole family can enjoy. Roberto was very knowledgeable and my kids had a great time with the hike and all the caves. The experience was just as described in his website and exceeded expectations. I would highly recommend this tour when in Tuscany. It was nice to get away from the crowds as we were the only few on these paths.

(Review from Tripadvisor ).

Roberto led us to discover the islands of Capraia, Elba and recently Sardinia, each time far from clichés and traditional tourist approaches. His sense of organization and guidance always reassures, his taste for culture and his way of sharing have always motivated us. Walking with Roberto is entertaining, rewarding, never obvious and his sense of empathy makes it never tiring.

The first trip we made with Roberto was on the Via Francigena, a beautiful experience, discovering typical landscapes, walking along hills that open up under villages that still retain their medieval appearance. Everything has been organized with skill and professionalism, both the restaurants and the accommodation, always characteristic and welcoming. Since then we have always remained in contact and, to that, other treks followed, last in the Ogliastra, wild area of ​​Sardinia, where sea and coast surprise you at every corner with their enchanted views. An experience to be recommended … and to be repeated!

WalkItaly Tours founder, seasoned walker, multipurpose rower and hectic tour guide, Roberto Carpano may not have won any Olympic medals, but he can reveal the secrets of Tuscany’s ancient walking trails and explain how to adjust your scull to optimize your rowing experience on the Tiber. Roberto has a penchant for good food and wine, and for Negroni cocktails.

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A self-guided adventure from inn to inn

Self-guided walking in tuscany, 7 nights — from usd1460.

Our Self-Guided Tuscany walking tour is a more relaxed version of our  hiking tour  in the same region: the Val d’Orcia, famed for its hilltowns (like Pienza, Montalcino and Montepulciano) and for its breathtaking landscapes. You start the tour with a night in Siena and then walk in stages through the Val d’Orcia, with stops of two nights in Montalcino and San Quirico, and your final night in Montepulciano. You can also opt to do just a portion of the walk. Either way, we provide you with all the tools you need to help you put your spirit of adventure into action.

• Explore the hilltowns of Siena, Montalcino, Pienza and Montepulciano
• Take daily walks, from one hilltown to the next
• Explore the villages of San Quirico, Bagno Vignoni and Montichiello
• Enjoy great Tuscan cuisine and wines

Depart From: Siena

Finish In:  Chiusi

Starting Dates: Any day, all year long

Fitness Rating: 2-3 (Ratings Explained)

"...incredibly scenic..."

We loved Italy and wish we could have spent more time. Everyone at Girosole was extremely polite and helpful, you helped make our trip truly memorable. We have to really thank Paolo who was always on time, courteous, and willing to help us with restaurant or travel information. He always managed to transport our baggage without ever a problem, and there were never problems checking into our rooms. The walk thru the Val d’Orcia was incredibly scenic, and from Rocca d’Orcia you overlook it all. We managed to eat our way thru Siena, Montalcino, San Quirico, Pienza and Montepulciano and the great perk of it all was that the walking burned it all off. We had many enjoyable picnics like this one in our photo of the Cappella di Vitaleta, which your walking directions led us to one fine day outside Pienza. The scenery was so beautiful, and we have tons of pictures and video to remember our trip by. So thanks again and good luck with the coming season!

Get the full tour details

Itinerary outline, here is an outline of a suggested daily itinerary. you can shorten or lengthen this tour to fit your travel dates. for further information, please request a detailed itinerary..

• Day one : You start in with arrival in Siena, arguably one of Italy’s most beautiful hilltowns, where there is plenty to do and see. You’ll not want to miss seeing the Campo, Siena’s remarkable central square, and the Duomo, with its stunning facade.
• Day two : Your tour rep arrives mid-day to bring you to Montalcino, where you enjoy a warm-up walk in the surrounding countryside, famous for the production of Brunello wine. (Walk distance: 3.5 miles/6 km – climb total: 1070 ft/330 m)
• Day three : Your walk today takes you to the small village of Castelnuovo dell’Abate, near which sits the beautiful romanesque church of Sant’Antimo, built of alabaster and travertine. You return to Montalcino for a second night. (Walk distance: 7.5 miles/12km – Climb total: 450 ft/150 m)
• Day four : From Montalcino, you walk to San Quirico, a small agricultural village filled with gardens and charming streets. (Walk distance: 8 miles/13 km – climb total: 580 ft/180 m)
• Day five : Today you enjoy a ring walk in the area of San Quirico and Rocca d’Orcia, passing through Bagno Vignoni, which is built around thermal springs in use since Roman times. (Walk distance: 8 miles/13 km – climb total: 1490 ft/460 m)
• Day six : You set off for Pienza, the hometown of the 15th C. Pope Pius II, whose experiments with urban renovation gave an impressive new face to this little town. (Walk distance: 5 miles/8 km – climb total: 980 ft/300 m)
• Day seven : Your last day of walking brings you from Pienza to Montepulciano, home to the Sangiovese Vino Nobile di Montepulciano. (Walk distance: 8.5 miles/13.5 km – climb total: 1070 feet/330 m)
• Day eight : We help you on your way to your next destination with a transfer to Chiusi on the main Rome-Florence train line.

What’s Included

We suggest the following inclusions based on the proposed itinerary (above) and prices (below). keep in mind that you can modify these as per your own preferences..

• 7 nights accommodation with en-suite facilities
• 6 days of walking
• breakfast each day
• GPS app with walk coordinates and emergency contact
• detailed maps and route descriptions
• a descriptive guide of the various sites to see
• a Tour Rep to oversee your tour and move your luggage each day
• travel guidance for pre/post-tour activities

(Not included are airfare, wine and other beverages with alcohol, personal purchases such as laundry, phone calls, frigobar items etc., and anything not specifically included above.)

“...more than we ever dreamed of...”

When people ask how we liked our trip to Italy, we respond with…we enjoyed seeing Venice, Florence and Rome and all they had to offer but if we could only pick one place…it would be our walking tour through Tuscany! It was more than we ever dreamed of. We chose the “comfort level” for our accommodations and throughout the trip we wondered what the higher level of accommodations would be like because ours were fabulous!

It’s even hard to pick which hotel was our favorite because the views and food were incredible. We were very fortunate to have another couple from Canada doing the same hikes we were so we agreed to hike together and they were the perfect fit! They made our trip even better! As we sat together in a Tuscan valley eating Pannies for lunch made by an elderly Italian lady and sipping Brunello wine we felt like we were living in a dream. We have so many wonderful memories of our hike. It was the perfect vacation! We look forward to going back for another hike through Tuscany someday but how could it get any better than what we had?

Thanks for the best vacation of our lives!

We price this tour for the following categories of accommodation . You can keep your tour private to your own group or you can open your tour for other travelers to join. Single Supplements (sing. supp.) are charged on single occupancy rooms only.  All prices are quoted per person in USD.

You can schedule this tour to start on any day of the week, all year long. As with all our tours, you tell us the dates you would like to start your tour, allowing you the maximum in flexibility and convenience ( full explanation ).

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19 Best Walking Tours in Florence to Explore Tuscany’s Heart

• 5 Pinterest

Jamp-packed with monumental sites and centuries-old attractions, these best walking tours in Florence take you on an authentic adventure, from history-focused excursions to expeditions highlighting Florentine cuisine.

In the table below, you’ll find our top picks . Whether you prefer a comprehensive exploration of Florence’s highlights, a unique culinary experience with a cooking masterclass or an enchanting evening atmosphere with a night photo walking tour.

Want to dive straight in? Browse our catalog now!

• all Florence walking tours

1 – Skip-the-Line Florence Highlights and David Walking Tour

Rating: ⭐️ 5/5 ( 651 reviews )

“This was a fantastic way to get acquainted with Florence and get into see Michaelangelo’s David. Our guide, Giacomo, was very knowledgeable and just so pleasant to talk with. He was very good at handling the group and sharing his vast knowledge of the city and history.” Susan, Viator

Discover Florence’s iconic treasures, including Michelangelo’s ‘David,’ with Italian Vista Travel’s walking tour. Skip the lines at the Accademia Gallery for an exclusive viewing of this renowned sculpture. Explore other Renaissance marvels like the Ponte Vecchio and Pitti Palace. Stroll through vibrant landmarks like Piazza della Republica and Piazza della Signoria, where impressive sculptures await your admiration.

Summary of the tour:

• Explore iconic landmarks like Piazza della Republica, Piazza della Signoria, and the Ponte Vecchio bridge.
• Admire the opulent Pitti Palace and the legendary Duomo.
• Enjoy skip-the-line entrance to the Accademia museum to view Michelangelo’s world-famous David sculpture.
• check offer
• Professional local guide
• English, German, Chinese (traditional or simplified),  Russian, Portuguese, Italian,  French, Spanish
• Choose between a morning or afternoon excursion
• The tour includes skip-the-line access to the Accademia Gallery
• It does not include entrance fees to the Cathedral and Dome
• Headsets are available for groups larger than 10
• You can upgrade to a private tour instead of a shared group one

After exploring the famous art gallery, the important landmarks, the designer boutiques along Via Tornabuoni and a handful of artist workshops in the Oltrarno neighborhood, you’ll feel like a proper local! With group size limits capped at 15, you’re able to move swiftly and efficiently through the city!

2 – Cooking Masterclass & Food Walking Tour

Rating: ⭐️ 5/5 ( 48 reviews )

“Wonderful experience, chef Catarina was very knowledgeable and taught us how to make some incredible Italian dishes in addition to providing lots of detail about the region’s cuisine, history, and local shops. Truly an incredible way to experience and learn Tuscan cuisine.” Audrey, Viator

Indulge in Florence’s culinary delights with Florencetown/Towns of Italy’s food-focused walking tour. Led by an expert chef guide, explore the historic bottegas of Oltrarno, sampling Tuscany’s finest produce along the way. Gather fresh ingredients for a hands-on cooking session back in the kitchen, where you’ll whip up a classic Italian three-course meal while savoring local Tuscan wine.

• Experience a guided food tour of Florence’s historic food bottegas with a chef.
• Sample the wares at traditional Florentine bottegas.
• Learn to create dishes like gnocchi, cannelloni, and risotto under the guidance of an expert chef, followed by a delicious homemade lunch accompanied by Tuscan wines.
• Guided tour with chef
• Food tastings at the Bottegas are inclusive of tour costs
• Receive a free booklet with recipes to take home
• After your cooking class, you’re awarded a Graduation Certificate B
• Group/class sizes are limited to 10 pax
• Inform the tour operator of any food allergies/intolerances in advance
• In the case when the bottegas close, enjoy extra food tastings during your lesson

It doesn’t matter if you’re an amateur or a pro chef, this tour and cooking class is for anyone with a passion for food! There’s nothing more authentic than hearing locals tell you about regional ingredients and the lay of the land! In case you were wondering about the dishes, they vary from the likes of gnocchi to cannelloni fiorentini .

3 – Florence by Night Photo Walking Tour with a Professional Photographer

Rating: ⭐️ 4.5/5 ( 15 reviews )

“This was an amazing experience, we really enjoyed Eva’s creativity, knowledge and learnt so much about settings and we benefitted from her local knowledge of Florence too. We would definitely recommend as it was one of our highlights of visiting the city and a wonderful photography experience. ” Mike, Viator

Explore Florence’s enchanting nighttime charm with YourDreamPictures by Eva Perocsenyi. Led by a professional photographer, capture the city’s illuminated beauty as ancient alleys and grand buildings come to life under the moonlight. Discover the best angles and lighting techniques for night photography while immersing yourself in Florence’s captivating architecture.

• Explore the magical Renaissance capital of Florence after sunset on an evening photo tour.
• Receive photography tips and techniques from a local photographer guide, suitable for any skill level and camera type.
• Choose between 2-hour or 3-hour tour options for flexibility, with the option of a private tour for personalized attention and a customizable itinerary.
• Professional photographer tour guide
• English and Italian
• Depending on the day, itineraries may vary
• This is a private tour for your group only
• This is not a guided sightseeing tour with commentary; it aims to highlight the best spots for photo-taking
• Please bring your own equipment along; cameras, etc are not provided (you can use a digital camera or mobile phone)
• Start times vary slightly depending on the season, in winter they begin a little earlier

the city), and your guide will show you all sorts of techniques, for example, the best angles and most photogenic backdrops! Florence feels completely different in the evening, transforming after sunset.

4 – Guided Walking Tour

Rating: ⭐️ 4.5/5 ( 1126 reviews )

“Our tour guide, Ali, was great! He was knowledgeable and friendly, showing us many of the significant places including detailed history and anecdotes. Very enjoyable experience.” Robert, Getyourguide

Delve deeper into Florence’s iconic landmarks with My Green Tour srl’s informative sightseeing excursion. Explore the historic Santa Maria del Fiore Cathedral, the renowned Piazza del Duomo, and the captivating Piazza della Signoria. Discover the stories behind these marvels and learn about the city’s influential figures and powerful families.

• Live, expert tour guide
• English, Italian, French, German, Russian, Spanish
• A free luggage deposit is available if you need to store your bags
• Join an open tour or request a private tour

For a complete serving of history, architecture, art and beauty, you can’t go wrong with this walking tour. It’s the perfect option if you only have a few days in Florence as it’s only 1.5 hours, but you get to see the most noteworthy tourist attractions in the Tuscan capital .

• walking tours in Florence

5 – Mysteries of the Medici Guided Walking Tour

Rating: ⭐️ 4.4/5 ( 591 reviews )

“The story of the Medici in a very exciting and graphic way and makes you want to hear more about Florence and its history. We also appreciated the recommendations for aperitif visits with a view. Although my kids – young adults – are usually not that enthusiastic about history and culture, they really enjoyed the tour with Viktoria.” Carole, Getyourguide

Explore the legacy of Florence’s renowned Medici family, who shaped the city’s destiny during the Renaissance. Delve into their history and influence on an excursion by My Green Tour srl, visiting their former residences and the Medici Chapels. Discover commissioned artworks and intriguing facts about this influential dynasty.

• Live, expert multilingual tour guide
• English, Spanish, French, Portuguese, Italian, German, Russian
• You have two options: a shared group or private tour
• Admission to the Medici Chapel is included, but you must select this option when booking this expedition
• Please be there 10 to 15 minutes before the starting time

From stories about how a banking family rose to such power to tales of rivalry between the Medicis and other Italian families like the Strozzi and Pazzi, walk away from this experience having learned something new!

• see price and reviews

6 – Free Tour: Renaissance and Medici tales

“The story of the Medici in a very exciting and graphic way and makes you want to hear more about Florence and its history. We also appreciated the recommendations for aperitif visits with a view. Although my kids – young adults – are usually not that enthusiastic about history and culture, they really enjoyed the tour with Viktoria.” Carole, Guruwalk

Explore Florence’s highlights with GuruWalk’s knowledgeable guides, delving into the city’s rich history and Renaissance heritage linked to the Medici Family. Led by passionate locals, uncover hidden gems and secret spots not typically found on tourist routes. Experience the iconic Cathedral of Santa Maria del Fiore, the Riccardi Medici Palace, and the Baptistery of San Giovanni, immersing yourself in the city’s vibrant atmosphere. Although the tour only covers exterior views, numerous stops ensure a fulfilling experience.

• free walking tours in Florence
• Licensed tour guide
• English, Spanish, Italian
• Your tour guide will be holding a red flag at the departure point
• Florence is the hometown of your guide
• The excursion is free, but gratuities are always welcome/a nice gesture

This journey prides itself on directing participants away from the usual tourist routes! Some city explorations can become boring/stagnant, feeling more like a lecture. With this descriptive venture, time flies by as you’re fully immersed in the painted literary pictures. With free walking tours, gratuities are based on your experience, and if you’re unsatisfied with the tour, you won’t feel as if you’ve wasted a whole bunch of euros!

7 – Renaissance & Medieval Florence Guided Walking Tour plus mobile App

Rating: ⭐️ 4/5 ( 139 reviews )

“Helena was a great host and was very knowledgeable. We ticked all the main boxes with her. Highly recommended!” Katie, Viator

Discover Florence’s highlights on CAF Tour and Travel’s classic route, starting from the San Lorenzo neighborhood near Piazza del Duomo. Explore the historic center, Centro Storico, including the famous leather market and the Mercato Nuovo, where you can rub the nose of the bronze pig for good luck. Admire Giambologna’s ‘Rape of the Sabine Women’ sculpture, learn about Italian poet Dante at ‘Casa di Dante’ and Badia Fiorentina, and visit Bargello Palace, once a prison.

• Local expert guide
• The stops along your route may be reordered on the day
• This city exploration comes with an extra mobile app self-guided itinerary (download VOX CITY from the App or Play Store)
• Tour group size is capped at 20 pax

Differing slightly from the rest, this tour includes an extra audio Guided Tour app to download before the expedition begins for even more insights and details during the walk. Live commentary is included as well, highlighting the art of the Renaissance, antics of the Medici family and city politics spanning the last centuries.

8 – Private Florence Walking Tour

Rating: ⭐️ 4.5/5 ( 54 reviews )

“Our guide Andrea was amazing! He knows everything about Florence and could answer all our questions. Three hours were gone as a few minutes. Thanks a lot Andrea!” Stephan, Viator

If there’s a particular facet of Firenze that you’re utterly fascinated with, private tours in Florence are the way to go!

Discover Florence’s iconic landmarks with CAF Tour and Travel’s personalized experience, tailored to your interests in art, history, or architecture. Visit symbolic sites like the Florence Cathedral, San Lorenzo district, Piazza della Signoria, Piazza del Duomo, Uffizi Gallery, and Ponte Vecchio. With the flexibility to choose your focus, you can explore at your own pace, pausing for further investigation at any point along the way.

• Local professional guide
• English, German, Italian, French, Spanish
• The only participants are the ones in your private party
• Personalize the stops on your itinerary but let the tour operator know when booking (this means the above route may differ)
• A hotel pickup is included if your accommodation is centrally located
• There are two tour time options: 9.30 AM and 2.30 PM
• Earphones are available for groups larger than nine

Be amazed by just how much knowledge your guide is filled with, whether talking architecture or city sculptures! For a private tour, this one is very well-priced and is a wonderful option for couples or honeymooners. It feels like a pukka Italian experience more than a conventional group tour.

9 – Small-Group Food Walking Tour

Rating: ⭐️ 5/5 ( 346 reviews )

“Our family had a wonderful time on the food tour. Every spot was tastefully chosen and we would’ve never found such great food simply wandering around on our own. On top of that our guide, Veronica, was an excellent and lovely person who made us feel right at home in Florence! 10/10” Andre, Viator

Experience the essence of Florentine cuisine with Fat Tire Tours Holdings LLC – Italy’s food tour. Dive into traditional delicatessens, bakeries, markets, and cafes to savor the city’s specialties. At the San Lorenzo Market, mingle with locals and sample cheeses, cold cuts, olive oils, and balsamics. Indulge in authentic espresso and conclude your culinary journey with delectable gelato.

• Local Guide
• Food and wine tasting included (vino samplings are only for participants over 18 years old)
• Bring extra spending money if you wish to purchase anything at the market
• Tours are limited to 12 participants

Your spirited foodie guide makes you fall in love with Italian cuisine even more, and you get to see first-hand just how much food means to locals — ingrained into everyday life and a huge part of Italian culture!

You’re shown the hotspots frequented by Florentinians, from a local coffee bar to a delicatessen that’s been around since 1885! Here, melt into seventh heaven when taking a bite of its special truffle pâté sandwich ( panino tartufato )!

10 – Renaissance Secrets Walking Tour with Gelato

Rating: ⭐️ 5/5 ( 17 reviews )

“Five stars for Rocher! A great tour, superb knowledge and really friendly chap. Very accommodating of us and our slightly grumpy baby. Excellent (and I mean faultless!) English. Humoured my attempts at Italian. Strong strong recommend. If we had more time we would have done more of his tours – don’t hesitate to book. Highly professional and well worth it.” Mariia, Getyourguide

Embark on a captivating journey into the world of Florentine art with Florence with Elvis! Delve into the transformative era of the Renaissance, which reshaped art in Florence, moving beyond religious themes. Explore the impact of influential families like the Medicis on the city’s artistic landscape.

• Live tour guide
• Headsets are provided for during the tour
• No matter the weather the tour will take place
• No oversized bags or luggage on wheels is allowed on this tour

Accommodating travelers of all ages, this affordable walking tour is baby-friendly. Your tour guide speaks excellent English and the incredible service keeps travelers returning to this tour operator! Learn more about important figures like the artists Michelangelo, Leonardo and Raphael and explorers such as Amerigo Vespucci.

11 – Heart of Florence Guided Walking Tour

Rating: ⭐️ 5/5 ( 10 709 reviews )

“What an amazing experience… This is the perfect walking tour to know the history center of Florence and learn about it story. Deborah was an amazing guide and here enthusiasm was contagious. Worth it every minute!” Francisca, Guruwalk

Explore Florence like a seasoned resident with CAF Tour and Travel’s comprehensive walking excursion. Led by a knowledgeable guide, each site becomes a fascinating history lesson. Admire iconic landmarks like the Gates of Paradise and Loggia dei Lanzi’s sculptures. Stroll along Via dei Calzaiuoli, visit the Mercato della Paglia, and capture the beauty of the Fountain of Neptune along the way.

• Live local professional tour guide
• English and Spanish
• If there are any participants who speak different languages, the tour guide will provide commentary in both
• Headphones are available for groups larger than 10
• A pre-organized/downloaded app audio guide is also available
• Please dress accordingly for the sites included in your itinerary, specifically for religious institutes
• A lunch option is available but needs to be selected when booking this tour (drinks not included)

Creating a concise route, this tour covers not-to-miss highlights that lure in thousands of tourists daily. Visit all the famous squares, such as Piazza del Duomo and Piazza Signoria, prized palaces like Palazzo Vecchio and Palazzo Medici Riccardi, religious institutes including the Cathedral, the Baptistery of San Giovanni and Orsanmichele Church, and the most attractive streets in town.

12 – Sightseeing Walking Tour with a Local Guide

Rating: ⭐️ 5/5 ( 84 reviews )

“Our guide Aurora was very knowledgeable and enthusiastic and encouraged questions with a friendly attitude” Anthony, Viator

Discover Florence’s highlights with ease on Raphael Tours & Events’ city tour. Led by a knowledgeable local guide, you’ll visit iconic sites like the Florence Cathedral, Giotto’s Bell Tower, and the Ponte Vecchio bridge. Along the way, soak up fascinating anecdotes and insights about the city’s rich history. By the end of this enlightening excursion, you’ll gain a deeper appreciation for Florence’s status as the “City of the Renaissance.”

• Local live guide
• English, German, Italian
• This is a private tour for your booked group only
• Sizes are limited to 15 participants for a conducive and hyper-customized sightseeing excursion

If you’re short on time but can’t bear to miss out on any of the tourist attractions and Renaissance beauties, this two-hour tour is jam-packed! With all of the benefits of a private outing, feel no pressure if you want to pause to snap, like , a hundred selfies, posing alongside famous figurines!

13 – Dome Climb & Private Guided Sightseeing Walking Tour with Hotel Pickup

Rating: ⭐️ 5/5 ( 9 reviews )

“Our tour guide Lio was excellent. He met us at our hotel and gave us a great tour of Florence providing us with a great history of the city. He was very knowledgeable and passionate about his city and its art work. The Dome climb was not to be missed. Amazing views in all directions!!” Christopher, Viator

Experience Florence’s iconic Duomo in a unique way with Private Tours of Florence . Led by a dedicated art historian, explore the historic center and learn about its rich cultural heritage. This private tour includes visits to landmarks like Piazza Santa Croce and Ponte Vecchio, immersing you in Florence’s art and history. The highlight is the Duomo , where you’ll skip the queues with included tickets and ascend Brunelleschi’s masterpiece. Don’t just admire its architecture—get hands-on with a climb up the dome for an unforgettable experience.

• Local professional art historian guide
• This excursion includes skip-the-line tickets and entry to all activities and attractions covered in the tour
• A hotel pick-up is inclusive for participants centrally located
• This is a private tour for your booked group only, and the expedition begins from your hotel
• As you’re walking around for three hours, a decent fitness level is required

We’re mega fans of the combination of a walking tour and a climb up the icon of Florence, which feels slightly more immersive compared to other tours. As a private excursion and with such a remarkably talented guide in charge, you feel as if you’re in the best of hands!

14 – Artisan Workshops: Private Walking Tour in Florence

Rating: ⭐️ 5/5 ( 6 reviews )

“This was a unique opportunity to learn about the history of craftsmen in Florence and visit smaller artisans’ workshops that otherwise would be impossible or at least, difficult to visit on one’s own. I was impressed by the variety of types of art as well as the unique opportunities to speak with, tour the workshops of and see the processes of artisans, including many whose styles and techniques are unusual. A wonderful tour!” Sarah, Viator

Experience Florence’s rich artistic heritage with Artviva The Original & Best Walking Tour. Delve into the world of artisans as you wander through the city’s historic streets, visiting workshops and boutiques where creators practice their craft. From leatherworking to marbled paper and mosaic making, witness the skilled hands behind Florence’s renowned artisanal traditions.

• Live professional personal shopper guide
• This is a private and personalized experience for your tour group only
• Bring extra spending money if you want to purchase any of the artisanal products
• In case of a cancellation due to bad weather or low numbers, choose a new date or receive a full refund

The streets swarm with creatives, so this type of tour feels extra authentic! With your personal shopper, you’ll get to see how leather bags are constructed, or check out wood carvings in person! Other stops include a perfume shop, goldsmith, paper marbling workshop and a lithograph maker.

15 – Private Photo Walking Tour

Rating: ⭐️ 5/5 ( 25 reviews )

“Eva was great and I would highly recommend this experience. She was very knowledgeable and helped with photography composition and locations around Florence.” Elizabeth, Viator

Capture Florence’s beauty from the best angles with YourDreamPictures by Eva Perocsenyi. Led by a local photographer, this tour ensures you snap ultra-photogenic shots of the city’s magnificent architecture. Whether you’re a novice or seasoned photographer, the guide offers expert advice on settings and compositions. Cruise past iconic landmarks and through ancient alleys at your own pace, relishing the intimate experience of this private tour.

• Professional photographer guide
• There are multiple tour length options (select yours when booking your tour)
• This tour focuses on photography, from bettering your skills to showing you the most photogenic spaces. It doesn’t focus on the history, art or food of the city.
• It doesn’t include entrance fees to any landmarks or activities
• Bring your own gear; mobile phone cameras are welcome (influencers)

This is an excellent option for novice photographers as well, with your professional guide there to aid and assist along the way. Walk away with a new skill set — even if you’re not in the industry- boost your social media pages, and learn how to shoot like one!

16 – Skip the Line Academy Guided Tour with Guided Walking Tour

Rating: ⭐️ 5/5 ( 7 reviews )

“Manuela was an excellent guide – she navigated the logistics of access to the Academia with ease (no small thing!) and was great at pointing our and explaining the highlights that we were looking for.” Steve, Viator

Explore Florence without the hassle of long lines with Italy Pass tours’ skip-the-line option. Wander through iconic sites like San Marco Square and Palazzo Vecchio before heading straight into the renowned Accademia Gallery, one of the best museums in Florence .

• Via Ricasoli, 47, Via Ricasoli, 47, 50121 Firenze FI, Italy
• Lindt Chocolate Shop Firenze Duomo, Lindt Chocolate Shop Firenze Duomo, Piazza del Duomo, 15R, 50129 Firenze FI, Italy
• Private live guide
• English, Italian, French
• It includes skip-the-line tickets for the Accademia Gallery
• Tour group size is capped at 19 pax
• All entrance fees and any taxes are inclusive of this walking tour

Seeing some of the greatest works of art up close is goosebump-inducing, to say the least! Not only will you get to see Michaelangelo’s famous ‘David’ sculpture, but other works by the genius too, like Domenico Ghirlandaio, Sandro Botticelli, Caravaggio and da Vinci.

17 – Inferno Florence Guided Tour

Rating: ⭐️ 4.5/5 ( 28 reviews )

“the guide was very knowledgeable of the history about the area and how the different locations fit into the Inferno movie, and how they were a little ‘tweaked’ in the book. She also had good answers to questions that were raised. Made me appreciate the book and the movie even more.” sosa, Viator

Embark on a thrilling journey through Florence with a walking tour inspired by Dan Brown’s novel “Inferno.” Discover hidden symbols and ancient secrets as you trace the footsteps of the protagonist, starting at the Fountain of Neptune. Marvel at landmarks featured in the book and movie, including the Cerca Trova and Dante Alighieri Death Mask at Palazzo Vecchio.

• Sometimes, the tour may be operated as a multilingual excursion
• Entrance ticket to Palazzo Vecchio is included
• Participants need to have an average fitness level as it’s a walking tour
• A hotel pickup is available for an extra cost
• Tour size is limited to eight pax
• Children need to be accompanied by an adult

Follow in the footsteps of Dan Brown’s “Inferno” on a tour of Florence, where much of the novel’s action unfolds. Explore the city’s monuments that inspired the plot, immersing yourself in the literary world of Dante Alighieri’s journey to Hell. Perfect for those seeking a unique twist on traditional sightseeing, this tour offers a surreal and intriguing experience.

18 – Sunset Walking Tour with Wine & Food Tasting

Rating: ⭐️ 5/5 ( 1104 reviews )

“Martino was a phenomenal guide, giving us some of the history as well as the trivia and the personalities wherever we went. The food and wine was a great cross-section of Florentine culture. I would highly recommend anyone take this tour.” Adam, Viator

Experience the magic of Florence at sunset with Eating Europe’s guided food tour. Delight in local delicacies like pecorino cheese and handmade pasta, and learn to craft the perfect Negroni cocktail. Explore secret wine tours and enjoy tastings in the charming Oltrarno neighborhood. Cheers to a memorable evening filled with delicious food and stunning views!

• Local foodie guide
• All food samplings, wine tastings and cooking demonstrations are included in the price
• If you want to purchase more drinks, you will need to pay for these individually
• Travelers with dietary requirements or food allergies can email these to the tour operator beforehand
• A minimum of two participants is required for the tour to happen, group sizes are maxed at 12 pax

Arrive hungry and thirsty for this tour, featuring 14 tastings across six locations. Experience the lively restaurant and bar scene as Florence comes alive. Highlights include visiting a centuries-old wine cellar and savoring Tuscan wines like Chianti Classico.

19 – Legends of Florence 2-Hour Walking Private Tour by Night

Excellent Guide! Share the history of this beautiful city with a pro! Christine, Viator

Experience Florence in a whole new light with ACCORD Italy Smart Tours & Experiences’ private night tour. Explore the city’s legends and mysteries as historical buildings take on a new allure under the moonlight. Visit squares with dark pasts and hear chilling tales of Florence’s tumultuous history. Dive deep into the city’s secrets, from medieval execution sites to infamous crimes. It’s a unique journey through Florence’s hidden stories, perfect for those seeking a different perspective on this historic city.

• Licensed guide
• English, Italian, Spanish
• In case the tour operates as a dual-language expedition, the duration is extended to 2.5 hours
• If you require a tour that’s not in english, let the operator know when booking
• Earphones are available for large groups
• This tour is exclusively for your private group

Navigating the streets at night can be tricky, so having a guide is a smart move. Opting for a nighttime tour during the summer helps beat the daytime heat. Brace yourself for some gruesome topics—you’ve been warned!

• walking tours in Florence at night

How to book walking tours in Florence?

A destination hotspot for travelers and explorers from around the world, there are many companies offering walking tours in Florence to keep up with the large crowds.

As a result, there are just as many travel websites selling these tour packages online, offering discounts and other extras.

Prices vary slightly from one tour operator’s website to the next. This is when our TourScanner search engine comes in handy!

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Spotlight on Tuscany

About this tour.

Discover the rolling hills of Tuscany, home to sprawling vineyards, charming medieval hill towns, and enchanting cities. Savor a 7-night stay in Montecatini Terme, the famous resort and spa town. Visit Pisa, Florence, and San Gimignano in the Italian countryside. Discover the charming town of Lucca, Italy’s best-kept secret. Learn about the heroic deeds of WWII at remains of the Gothic Line and visit the Museum of Liberation. Enjoy free time to explore the cultural treasures of Florence. Partake in a Tuscan cooking class. Sample cheese at the farm where it is made. Enjoy fabulous local wines and the region’s famous cuisine. Steeped in history, culture and legend, this is Tuscany as you always imagined it.

Your Tour Includes

• 1 Handpicked Accommodations
• 2 Choice on Tour Options

Included Highlights

• Montecatini Terme
• Gothic Line
• Winery Tour

Your Tour at a Glance

7 Breakfasts

Travel Style

Best time for travel, customize your tour.

$1,199.00 pp

Optional Excursions

Starting at $140.00

Activity Level

• Level This Tour

For specific details about this tour's activity level and other info to know before you book your trip, click here.

Extension Style

Best time for travel spotlight on tuscany.

While just about any month is great to visit Tuscany, there are a few prime times of the year for the Spotlight on Tuscany tour. Here are some recommendations from our destination experts.

Winter: Enjoy beautiful Cinque Terre during the winter months, with smaller crowds.

Spring and Fall: In March and November, enjoy the calm atmosphere, especially in Cinque Terre, which becomes quite crowded from April through October. While some seasonal attractions might not be open, countless opportunities to soak in the area’s beauty remain.

Travel Styles

Highlights and inclusions.

Must-See Inclusions:

Stay in the famous spa resort town of Montecatini Terme for 7 nights.

• Journey to Florence for a tour of the "Cradle of the Renaissance."

Stop in the medieval city of Lucca, encircled by 16th-century walls.

Cultural Experiences:

Step to the front of the line to see Michelangelo’s famous statue of David.

See the Gothic Line, one of the Germans’ last lines of defense during WWII.

Retrace the steps of ancient pilgrims as they crossed the Devil’s Bridge in the Serchio Valley.

Culinary Inclusions:

Sample delectable wines during a wine tasting at a local farm.

Spend time at a cheese farm to taste flavorful pecorino cheese.

Learn about Tuscan cuisine during a cooking class.

• Choice on Tour
• Cooking Class
• Cheese Farm
• San Gimignano

Book with Confidence

* With Insurance Purchased

• *No Hassle Refunds
• Traveling Well Safety
• No booking fee, *no change fees
• Top Rated Travel Protection

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Getting Prepared

Know before you go, travel tips, enhance your tour.

Pre and Post Tour Extensions

• Choice On Tour

Unique Experience

Cultural Experiences

Enhance Your Trip

• Tour Extensions

Today you have the choice between 2 activities. Your first option is to learn more about Montecatini’s curative waters during a guided walking tour of the city. Discover the town’s elegant Art Nouveau architecture and visit the historic Tettuccio Spa,* known for the health benefits in its mineral waters. Your second choice is to journey to Siena and embark on a walking tour through its narrow Gothic streets. Take in stunning palaces, mansions and the historic Piazza del Campo along the way. Then, get to know local life in a contrada (neighborhood) whose community life is centered around the colorful Palio horse race.

Begin your trip with a 3-night sojourn in the Eternal City. Toast to your Roman getaway with a welcome dinner in a local restaurant. See the city with an expert guide, including an in-depth tour of the Colosseum and Roman Forum. Enjoy ample free time to explore Rome's charms or join an optional tour to the Vatican Museums and St. Peter's Basilica.

• Overnight Flight
• You are on your way to the eternal city of Rome.
• Rome, Italy - Tour Begins
• Get settled into Rome for your 3-night stay. Take time to get acquainted with the area on your own. This evening, join your fellow travelers for a welcome dinner featuring regional delicacies.
• Rome - Optional Excursion
• Start your morning with a ride on La Metro – Rome’s underground system. First stop – a locally guided tour of Classical Rome. During an in-depth visit to the Colosseum, your guide recounts its rich history. Then wander along the Roman Forum and the Via Sacra, traversed by the likes of Julius Caesar and Marc Anthony. The remainder of the day is yours. Perhaps you will join an optional dinner in a popular restaurant, where you’ll indulge in a hearty meal accompanied by wine and local entertainment.
• Make the most of a free day in Italy’s capital city. Perhaps you will join an optional tour* in the morning to the Vatican Museums and St. Peter's Basilica, taking in world-renowned wonders such as the Sistine Chapel and Michelangelo’s mural of the Last Judgment. In the afternoon, consider strolling through the Borghese Gardens for views of the city’s skyline or meander through Rome’s bohemian Trastevere district.
• Rome - Montecatini Terme
• Your Roman sojourn comes to a close today. Say Arrivederci Roma as you transfer to Montecatini Terme to begin your tour of Tuscany.

Extend your Italian adventure with a 2-night stay in Bologna, Italy’s foodie haven. En route, visit a Parmigiano-Reggiano cheese farm, and a Balsamic Vinegar producer aging their barrels in the attic, as countless generations did before them. Your culinary exploration continues with a demonstration of authentic gelato making and a walking tour of Bologna, home to the oldest continuously operating university in the western world and birthplace of some of Italy’s most iconic foods: tortellini, mortadella and Bolognese sauce. Buon Appetito!

• Montecatini Terme - Food Valley Tour and Tastings - Bologna
• This morning, traverse the Apennine Mountains and cross from Tuscany into the Emilia region, Italy’s foodie haven. Visit a local farm producing Parmigiano-Reggiano cheese according to traditional codes dating back to the 1300s. Then pause for a light lunch at a nearby villa where the family still ages their Balsamic Vinegar production in the attic, as countless generations have done before them. Your exploration of Emilia’s Food Valley concludes with a demonstration – and tasting – of authentic gelato, before arriving in Bologna, your home for the next 2 nights.
• Bologna - Walking Tour - Food Tour
• Spend the morning exploring Bologna in company of an expert guide. During your walking tour, discover the origin of Bologna’s several nicknames – la dotta (the learned) and la rossa (the red, from the colors of its bricks) and la grassa (the fat). Perhaps the latter nickname is the most fitting. Food is a true passion here, as Bologna is the birthplace of some of Italy’s most iconic foods: tortellini, mortadella - the progenitor of baloney - and Bolognese sauce. Visit the ancient seat of the University – the oldest continuously operating in the western world – before browsing Bologna’s specialty food shops. Then, sample local delicacies such as Parma ham and lasagna during lunch at a local eatery. Spend the afternoon at leisure in this lively town. Indulge in some people-watching at a café in Piazza Maggiore, the expansive plaza at the heart of the city’s social life, or search for Bologna’s very own leaning towers: the Garisenda and Asinelli. Whatever your interest, Bologna guarantees the perfect stroll as it boasts over 23 miles of covered sidewalks lined by colonnades offering protection from rain and heat.
• Bologna - Extension Ends
• Bid arrivederci to Bologna as your Italian sojourn comes to a close today.

Spend a glorious day exploring the unique Cinque Terre. You’ll discover a magical land nestled between the mountains and the Mediterranean that is nearly inaccessible. Travel by rail and boat,* past terraced vineyards and stunning panoramas on your way to a string of colorful fishing villages that sit along the area’s breathtaking, rugged coastline. Savor the charms of this special place with a local guide who will help you explore some of the delightful towns of the area. Hear tales of the region’s past and present as you come to know why the Cinque Terre National Park has been named a UNESCO World Heritage site. This is the perfect way to spend your day – feeling like you have stepped into a postcard.

Journey to Florence for a tour of the "Cradle of the Renaissance."

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Tuscany Walks

The Tuscan countryside is a region rich in history, culture, cuisine, and natural beauty. You will walk over rolling hills, through vast vineyards, and along paths trodden for thousands of years. You will experience cities that have birthed some of the world’s greatest masterminds and artists, ancient towns seemingly untouched by the modern world, and delightful traditional cuisine.

At the end of each night, you will be greeted by kind hosts at your comfortable accommodations, enjoy delicious cuisine made from recipes passed down through generations, and have the opportunity to taste exquisite wines from one of the most famous producers in the world. It doesn’t matter which path you take in this region, you will always find something extraordinary.

Hilltop Towns of Tuscany – 6 Days

Self-guided.

Explore the Tuscan hill towns of Volterra, San Gimignano and Monteriggioni, following Etruscan trails and ancient pilgrim routes to Siena.

• 5 nights ensuite room accommodation in Guesthouses & 3* Hotels
• All luggage transfers
• All taxi transfers as described in the itinerary
• Flexibility to add or remove days
• 5 breakfasts
• Maps, daily walk notes and information pack
• 24/7 telephone support
• Enjoy worry-free navigation with your comprehensive maps, walk notes and guidebook

Florence to Siena: Through the Chianti Winelands – 7 Days

Journey from the Renaissance city of Florence to the rolling hills of Tuscany’s Chianti wine region, ending at the grandeur of Siena’s Piazza del Campo.

• 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
• All luggage transfers taxi transfers as described in the itinerary
• 6 breakfasts
• Flexible itinerary to suit your walking needs
• 24/7 telephone support and enjoy worry-free navigation with your comprehensive maps, route notes and guidebook

Classic Trails of Tuscany: Siena to Montepulciano – 8 Days

Walk through southern Tuscany from Siena to Montepulciano. Explore hilltop towns, dine on rustic  dishes and sample Brunello wines from the UNESCO protected Val d’Orcia region.

• All luggage transfers and all taxi transfers as described in the itinerary
• Option to upgrade to a wine resort in Gaiole in Chianti
• 7 breakfasts and 1 dinner
• Enjoy worry-free navigation with your comprehensive maps, route notes and guidebook

Tuscany Explorer: Florence to Montepulciano – 10 Days

South of Florence, walk across the rolling vineyards of Chianti. Visit the medieval city of Siena and hike through the Val d’Orcia, to the hilltop town of Montepulciano.

• 9 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
• Flexibility to add or include days
• 9 breakfasts
• Flora and Fauna

ACCOMMODATION

Climate/weather, when to walk, walking fitness levels, walking essentials.

• Non walking activities
• Visit Florence, Siena and walk through splendour of Tuscany
• Explore the UNESCO city of Florence, birthplace of the Renaissance
• Stay in the Chianti wine towns of Radda and Gaiole in Chianti
• Walk through lyrical landscapes of golden wheat fields, vineyards, chestnut and olive groves
• Marvel at the grandeur of Piazza del Campo in Siena
• Follow ancient pilgrim trails deep into southern Tuscany
• Soak in the hot springs of Bagno Vignoni
• Spend each night in historic family run hotels
• Stroll through the cobbled streets and piazza’s of Montepulciano
• Picnic on local Pecorino cheese, cured meats and crusty bread
• Enjoy fresh bowls of pasta paired with local wine
• Visit medieval abbeys, hilltop towers and Romanesque churches
• Sample the award-winning Brunello wines of Montalcino
• Sample the world class Chianti wines of Volpaia and Brunello

The region of Tuscany has a rich and complex history. Originally, Tuscany was home to the wine-loving Etruscans but was annexed by Rome in 351 BC. After the fall of the Roman empire, the area was ruled by ever-changing powers until individual Tuscan cities began gaining their independence during the 12th century. While there were many wars between these city-states, they all accrued extraordinary wealth from trade, banking, agriculture, textile manufacturing, and, of course, wine.

Florence rose above the rest and introduced the world to the Renaissance by way of its flourishing artistic community. This incredible city was home to famous individuals like Michelangelo, Dante, Machiavelli, Leonardo Da Vinci, and more. While Florence declined in power after the Medici family died out, it still remained a central hub for the area. After Tuscany voted in favour of annexation to Italy, Florence became the capital of Italy from 1865 to 1871.

Today, Tuscany is still considered one of the significant cultural centres of the world. The museums, churches, and galleries, with their exquisite architecture and exhibits, garner millions of tourists each year who want to experience the height of Tuscany’s magnificent culture. The small towns receive almost as much interest with their ancient buildings, traditional foods, and kind townspeople.

Additionally, wine connoisseurs come to this region from around the world to learn about the origins of one of the world’s most excellent wine manufacturers. Tuscan vineyards, with traditions thousands of years in the making, produce some of the highest quality wines on the market. There are tastings around every corner, and tourists love the opportunity to sample such exquisite wines.

Flora & Fauna

Italy has a long-standing civilisation that has dramatically changed the natural landscape over the past few thousand years. Much of the original flora and fauna have been wiped out over time. When one thinks of Italy nowadays, they dream of the rolling pastures, abundant crops, and extensive vineyards that make up the landscape.

The flora of the Italy of today has been primarily established by humankind. The landscape is dotted with olive groves, pines, and cypresses. Vineyards and crop fields take up the majority of free space, so there are very few sections of untouched nature left. Yet, nature always finds a way to make itself known even if it is only the tiniest of flowers.

Come springtime, the grassy fields and rolling pastures will be adorned with stunning bursts of colour. Bright red poppies and white Marguerite daisies bring smiles to many. Wild roses and yellow gorse can be seen along the road as well as many types of orchids. Bee orchids, Orchiaceras bergonii orchids, and Pyramidal orchids are easy to spot if you know what to look for.

Initially, the Italian peninsula was home to species like ibexes, chamois, wolves, bears, marmots, and eagles. Now, it is rare that you will see one of these creatures wandering free in the wild. However, a few can still be found in isolated natural parks.

Today, you will still find smaller species out in the wild. One beautiful creature that can be found is the butterfly. Tuscany is located on the butterfly migration path from Africa to Northern Europe. Sixty species can be found making their way north at the beginning of Spring, including the very well-known Painted Lady. Other insects can be found among the grassy areas such as ascalaphids, dragonflies, and even hornets.

Italy is also home to 19 species of snake, and you may see one or two along your walking holiday. While most are harmless and unaggressive, it is best to stay out of their way. Frogs are also common to see when nearby water, and you will likely witness a lizard or two basking in the sun as you travel along the paths.

You may expect to see birds on the trail, but you likely won’t. Birds are not all that common in Italy given to the lack of resources available to them. However, you may be able to spot raptors, hoopoe, or owls in the evening.

During your walking holiday, you will spend each night in small boutique B&B’s as well as 3-star and 4-star hotels. Chosen for their location, facilities, and history, each accommodation welcomes walkers with a warm greeting. Many of them will be family-run, so they are very happy to chat about the local history, food and wines of the specific regions you will be walking through.

Hotel David

The award-winning hotel, Hotel David, was an 1800s villa that was transformed into a popular hotel in the 1950s. This classy hotel still holds the period furniture from the original dwelling, giving the hotel a homey and loving atmosphere. Comfortable rooms come with a free buffet breakfast, happy hour, minibar, and Sky TV. Hotel David prides itself on providing quality service while making each guest feel welcomed and at home.

Hotel Palazzo San Niccolo

Located in the heart of the historic centre of Radda is the beautiful Hotel Palazzo San Niccolo. It has been recently renovated to provide the best possible experience for its patrons. Enjoy dinner at the Caffe San Niccolo and wander through their private gardens after exploring the village. A pleasant night’s sleep awaits you in their comfortable rooms, ensuring that you are rejuvenated and ready to continue your journey the following day.

Cavarchino B&B

Nestled among the splendid vineyards and winding roads of the Chianti region is the Cavarchino B&B. This ancient farmhouse offers its guests old-world style combined with modern comforts. Magnificent views can be seen from every window and while swimming in the infinity pool. If that wasn’t enough, you can lounge in their personal gardens, read a book in their relaxation area, or just breathe in the fresh country air.

Hotel Chiuserlli

Built in 1870, this neoclassical villa is located in the heart of Siena. In 2013, the hotel was renovated to combine its old-world charm with modern amenities. Quaint rooms are perfect for singles, couples, and families to relax in. Sip a glass of wine on the terrace, explore the gorgeous city of Siena, or get pampered at their partnered spa, Antica Querciolaia, at a discounted rate.

Hotel dei Capitani

Located in the 18th century Catasto Leopoldino, in the historic centre of Montalcino, is the gorgeous Hotel dei Capitani. It is believed this building was used in the Middle Ages as a shelter for the Sienese people when they were fleeing from the Florentine Army. No signs of war remain today except for the swimming pool which is designed to look like a medieval fountain. Take advantage of the large, splendid rooms (some with two stories) that are waiting for you. Take a dip in the enchanting pool and ask the kind hotel employees about the best wines in the area. They will be more than happy to tell you all about them.

La Locanda Loggiato

La Locanda Loggiato dates all the way back to the 13th century. Fast forward to modern day and it’s the perfect blend of charm, simplicity, and romance. Owned by two amazing women, this accommodation will provide you excellent service with a smile. Enjoy bathing in the thermal pools, relaxing to the sweet sounds of nature, and getting special rates at the famous Bagno Vignoni Spa where you can be pampered to your heart’s content. Charming rooms await you here, promising an evening of peaceful rest before resuming your walking holiday the next morning.

Piccolo Hotel La Valle

Piccolo Hotel La Valle is made in the traditional style of stone and brick to give visitors a glimpse of simplistic beauty. The staff are kind and attentive, the rooms are made for relaxation, and the views are beyond gorgeous. The hotel boasts a sweeping panoramic view of the Val d’Orica; take it all in from the balconied rooms or while sipping a coffee on the expertly-manicured lawn. Before heading out on the next leg of your walking holiday, be sure to enjoy the goodies at the buffet breakfast included with your stay.

Hotel II Rondo

The Hotel II Rondo prides itself on maintaining a warm, old-world charm that leaves guests in a familiar atmosphere. Each bedroom is decorated with pastels, antique furniture, and handmade embroidered linen curtains. It will feel as though you are stepping back in time but with the enjoyment of modern amenities. One of the most spectacular parts of this stay is the buffet breakfast where everything is grown or made within 15km. Delight in seasonal fruits, local cheeses, sweet pancakes, and freshly made pastries in the elegant breakfast room or out in their gorgeous garden.

Albergo del Chianti

Albergo del Chianti is a perfect place for relaxing. Designed with peacefulness in mind, their rooms are structured to guarantee quietness and to suit all types of visitors. Take a dip in the shimmering blue pool or dine in their coastal-themed restaurant. If you are lucky, you may pass through this beautiful hotel during the time that the festivals are going on. Albergo del Chianti is perfectly positioned in the main square where art exhibitions, weekly markets, and colourful festivals are held. Right outside your door could be an authentic taste of Italian culture.

Pieve a Salti

Located among the green rolling hills of Siena is the gorgeous Pieve a Salti. The Prandi family have spent the past 30 years creating a paradise on their 700 hectares of farmland. Here you can eat organically grown food in the restaurant, relax in the spa, take a horseback riding adventure, swim in the outdoor or indoor pools, play tennis, go biking, or even hunt for mushrooms. Once the day is over, relax in one of their traditionally-styled Tuscan rooms that are both comfortable and charming.

Hotel la Cisterna

Take a step back in time to an age of simplicity at the Hotel la Cisterna. San Gimignano is steeped in age-old world culture, with travellers coming back again and again to experience its ageless traditions. The goal of Hotel La Cisterna is to provide the elegant warmth of hospitality. They pride themselves on having classically furnished rooms and excellent service. Dine in Tuscan style and taste secret recipes passed down from generation to generation, all while enjoying cascading views of the countryside.

As a part of your walking holiday with us, we will transfer your main luggage between accommodations. Therefore, you will only have to carry a light daypack as you traverse the Tuscan landscape. However, it is your responsibility to manage how you will arrive at the first city and how you will depart from the final destination. We have listed some suggestions below.

If you have any questions, please feel free to get in contact with your service representative; after doing so, we will happily guide you through your best options.

If you are arriving from a town or city near Florence, you will likely be able to catch a train or bus to the city’s two main railway stations. Firenze Santa Maria Novella (Firenze SMN) is located close to the city’s major tourist attractions. The second railway station is Firenze Campo di Marte, which is used by national and international train stations.

Arrive at: Florence

Florence has a small airport. The larger airports of Pisa and Rome generally offer a more comprehensive range of routes across Europe and beyond.

From Florence Airport: You can travel by either bus or tram from Florence airport to Florence centre. The direct tram services terminate next to the Florence mainline station, whereas the bus service terminates in central Florence. Both journeys are no longer than 20 minutes.

From Pisa Airport: From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Centrale station and change to a direct service to Florence. Journey time is approximately 1 hour to 1 hour and 30 minutes.

From Rome Airport: Rome has two airports: Fiumicino and Ciampino. Fiumicino airport connects through to Florence central station in around 2 hours and 30 minutes (with a change of trains in Rome central station). If you’re arriving into Rome Ciampino airport, you will need to take the airport bus to Ciampino station and change at Rome central station for services to Florence. Journey time from Ciampino to Florence is around 2 hours and 30mins (depending on times and services).

Arrive at: Sienna

From Pisa: You can take a unique “people mover” from the airport to the Pisa Centrale Train Station and then board a train to Siena. The trains leave every 30 minutes and the full journey takes approximately 1 hour and 45 minutes, with one transfer.

From Rome: Take a Leonardo Express Train into Rome centre and then board a train to Siena (however, you have to go to Florence, then change). The trains leave approximately every hour, and the journey will take around 3 hours and 30 minutes.

You can also take the Flix Bus from the Rome Tiburtina Bus Station for a direct trip to Siena that will take less than 3 hours.

From Florence: From Florence, you can take the train or the bus to Siena. The journey time by train is about 1 hour and 30 minutes. Some trains and buses are direct whereas on others you will have to transfer in Empoli. By taking the regional bus, you will be provided with a shorter trip that drops you off within the city walls.

Arrive at: Volterra

From Pisa: From Pisa, you can take the train service provided by Trenitalia from the Pisa Central Station. It will take approximately 1 hour and 30 minutes to arrive at the Saline Ex Coop Station. Here you will transfer to the bus to Volterra. It will take about 30 minutes to reach Volterra.

From Florence: Take the train from the Firenze SMN Station to the Pontedera – Casciana T. Station. It is approximately a 45-minute ride. Upon arrival, transfer to the Volterra bus line. It will take about 1 hour and 30 minutes to arrive in Volterra.

From Rome: To reach Volterra from Rome, you must first travel to Florence. You can take the Venezia S. Lucia line from Roma Termini into Firenze SMN Railway Station. From here, follow the same directions given above for traveling from Florence.

Depart from: Montepulciano

If departing from Montepulciano, there are a variety of buses that you can take from the Montepulciano Autostazione that will connect you to nearby train stations. Depending on where you wish to travel to, there are regular connections through to Florence, Pisa, and Siena.

Depart from: Sienna

If departing from Siena, you will need to take a train since the city does not have an airport. There are excellent train connections to Florence (direct service, 1hr 30mins), Pisa (change at Empoli, 1hr 45mins) and Rome (via Chiusi Chianciano Terme, 4hrs).

More Options:

For all train travel in Italy prices, timetables and ticket reservations can be made through The Trainline or Tren Italia . Another useful generic planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.

The region of Tuscany boasts an average of 2300 hours of sunshine per year with hardly any rainfall to break it up. In spring, the temperature starts to warm but the rainy season sets in. Luckily, the rain mostly dissipates by April and ushers in warm weather and average temperatures of 8°C – 19°C . In the summer months, the weather is sunny and can reach 40° C; at night, the weather rarely drops below 30° C .

Come September, the high temperatures begin to dissipate and temperatures range from 15°C – 27°C . Many tourists flock to Tuscany during this time as the sunny weather remains, but it’s no longer scorching hot. As winter approaches, the temperatures continue to cool and rain becomes more frequent.

You will be walking an average of 10km-19km per day with up to 500m of ascent and descent. You will be traversing a variety of landscapes including forest trails, gravel tracks, rolling farmlands, and vineyards, as well as within the towns and villages. It is common in Italy for there to be no separate footpaths, so you will often be walking along the edge of the road while in town; please be mindful of all road users when doing so.

For each of the walks, you will be provided with daily notes, a map, and the GPX tracks if you require them for use on your own device.

Our walking holiday runs from late April to the end of June and from mid-August through October, with departures available daily. To best enjoy the warm, bright days that this region has to offer, we avoid the rainy months of early spring and winter as well as the scorching heat of mid-summer.

During this time although there is generally very little rainfall, Tuscany does have some spectacular thunderstorms which usually occur in the late afternoon or evening. However, generally, the paths will be dry, and the spectacular scenery will be easily visible under the bright, clear skies. Plus, the grape harvest season begins from mid-August to September and with it comes lively local festivals that you may have the opportunity to enjoy. For more information on Tuscany’s seasonal weather, please see our climate/weather section.

The trails you will be walking through Tuscany are rated as moderate. The majority of these trails are well-defined, although some of the tracks may have short, steep hill sections or rough surfaces. You will be passing through a diverse set of landscapes, but none are considered particularly challenging in nature.

It is recommended that you have a moderately active lifestyle if you want to participate in this walk. You should maintain an exercise regime of 2 to 3 times a week and be able to walk 10km-19km per day. If you are unsure of your level of fitness, consult with your doctor.

Your main piece of luggage will be transported for you each day as you walk, so when you arrive at your accommodation, it will be there waiting for you. You will only have to carry a light day pack with your essentials.

As with any journey, it is essential to be prepared for your self-guided walking holiday. While we will be transporting your luggage from accommodation to accommodation, you will still be carrying a lightweight day pack with you. Here is what we suggest that you take with you each day:

• Walking notes, map and a map case
• Picnic lunch packed in an insulated container (when supplied)
• Waterproof jacket with a hood
• Quick drying fleece or jumper
• Sun protection (hat, sunglasses & cream, at least 15SPF+)
• Comfortable walking shoes or boots
• 2 to 3 litres of water
• First aid kit (including personal medication & insect repellent)
• Toilet paper
• Local currency and credit cards
• Mobile phone (please note that reception is not available in all walk areas)
• Small container of salt mixed with rice grains
• Any other personal effects
• And don’t forget to waterproof your bag!

Now that we have the essentials packed, it is time to think of any additional items that may be worth taking along with you. These items may include but are not limited to:

• Waterproof over-trousers
• Warm hat & gloves (if travelling early or late in the season
• Extra socks
• Camera (with an extra battery or SIM cards)
• Battery pack and charging cable for phone
• Notebook and pen
• Small torch
• Walking stick / walking poles
• Additional snacks

If you have any questions, please feel free to contact our office and have a chat with our friendly team. We will happily advise you on what types of clothing, backpacks, boots, and other materials you may need for your walking holiday.

Florence is considered one of the great cultural and historical centres of Italy and the world as a whole. Great artists were inspired by this magnificent city’s rich history and incredible architecture. A birthplace of art, science, and incredible food, Florence is one city where you could spend a lifetime and never experience everything.

Ponte Vecchio Bridge

The Ponte Vecchio, or Old Bridge, has stood the test of time and is one of Florence’s famous landmarks. The Ponte Vecchio was the only bridge across the Arno River into Florence until 1218. Even though it was soon destroyed by a flood, it was subsequently rebuilt in 1345; it miraculously survived World War II and another flood. Today you can walk across the bridge at any time and during business hours gorgeous shops line its sides. These shops have been here for hundreds of years and sell some of the most beautiful jewellery in all of Italy.

Uffizi Art Gallery

The Uffizi Art Gallery was not intended to become a famous museum where 10,000 tourists pass through each day. It originally served as a grandiose building for hosting magistrates when the Medici family was in power; “Uffizi” actually means “offices” in Italian. The Medici’s were avid art collectors, and eventually their collection was open to the public for everyone to enjoy. By visiting the Uffizi Art Gallery, you will be able to view some incredible art and take a veritable walk through history.

Galleria dell’ Accademia

It is here that you will have the opportunity to view Michelangelo’s David, a world-famous marble sculpture. David is featured in the centre of the hall, drawing countless visitors each year. However, he is not all there is to offer. Explore the rest of the museum to learn about botany, music, and art. If you can’t get enough of Michelangelo’s work, you can visit his Hall of Prisoners to see all the pieces that he didn’t finish.

Piazza del Duomo

In the heart of Florence, you can experience the magnificent architecture within the Piazza del Duomo. In this square, standing tall as one of Florence’s most famous landmarks, is the Cathedral of Santa Maria del Fiore (also known as the Duomo). This enormous Gothic structure was built on the ruins of a 7th century church, which can still be seen in the crypt. It took over 200 years to be deemed finished, and once you enter, you will understand why. The cathedral has a corresponding Bell Tower (which you can climb up) and a baptistery. It is simply not enough to see these structures from the outside, you must take the time to explore the inside as well!

Chianti Winelands

The Chianti Winelands is a region where the high-quality “Chianti Classico” wines are produced. It covers a range of towns, but only those within this region can put the famous black rooster symbol on their wine. Looking over the region is like admiring a painting. Green squares of vineyards, cypress-lined roads, and wildflowers add bright splashes of colours to the landscape. It is hard to believe that this area was once a constant battlefield, but out of war came beauty.

This tiny, fortified village is known to Italians as a “Castello.” It takes less than an hour to explore, but you will be amazed by the original Tuscan architecture that this town prides itself on restoring to its original grandeur. You can pop into one of the three restaurants for a snack or just take a moment to rest in the shade.

Santa Maria Novella Church

The Santa Maria Novella is considered one of the most important Gothic churches in all of Tuscany. Fra Jacopo Talenti and Leon Battista Alberti were the masterminds behind the exterior of this church. Inside, you can examine the spectacular works of Masaccio, Ghirlandaio, and Giotto. Another reason why this church is so famous is that it features the oldest façade in all of Florence. Moreover, it is the only church with its original façade still intact today!

This medieval town has been inhabited since the 9th century and was once the capital of Chianti. Located on an ideal hilltop location between the Arbia and Pesa valleys, this small town still has an ancient vibe to it. Massive defensive walls span the perimeter, narrow streets twine through the city, and towering buildings make you feel as though a knight will ride past at any moment.

This tiny hamlet in Salcio overlooks the Chianti vineyards and woodlands. Consisting of just a couple small stone houses and an ancient church that dates back farther than 1018, it is a joy to stop here and ponder what life must have been like centuries ago.

Gaiole is another important city to the historical and cultural creation of the Chianti Region. This city boasts exquisite castles and churches, a beautiful byproduct of the long-lasting power struggles between Gaiole and its surrounding Tuscan cities hundreds of years ago. Now, Gaiole is no longer focused on power but rather on wine. It is home to the largest winery in the Chianti Classico region where the Chianti formula was created in 1872. You will find no better location to hop from wine tasting to wine tasting than here.

Badia a Coltibuono

This hamlet used to be a monastery. It was founded in 1051 and was ruled by the Vallombrosan order of Benedictine monks for almost 800 years. This monastery held numerous manuscripts that have now been moved to the archives in Florence. After the monastery closed, it was transformed into a farm-house villa boasting an enclosed garden, medicinal plants, and natural decorations that will please any nature lover.

Badia a Passignano Abbey

This abbey was founded in 1049 in response to the Vallombrosan monastic reforms. It is perched on an isolated site that makes for a beautiful hike looking over the green landscape of the Chianti region. Within the abbey, you can see an ancient courtyard, the Church of Saint Michael Archangel, and the bell tower.

You may know Siena from the famous James bond movie Quantum of Solace, where you can see the city and the Palio featured. However, Siena is much more than just a quick stop in a movie. After being transferred to Siena, you will have the opportunity to explore this gorgeous city. It is said that Siena was founded by one of the legendary founders of Rome, depicted by the famous she-wolf statues all over the city. We suggest staying an extra day so that you can truly experience all that Siena has to offer.

Piazza del Campo

Formerly the meeting point of 3 primary routes in and out of Siena, the piazza was developed as a neutral meeting ground where political holidays and festivals could be staged. Featuring a unique design said to be in the shape of Virgin Mary’s cloak, the piazza attracts many tourists and twice a year hosts the colourful Palio horse event. Nearby the plaza, you can visit the Palazzo Pubblico, the Torre del Mangia, the Capella di Piazza, and the beautiful fountain known as Fonte Gaia.

Buonconvento

You will have the opportunity to take the train to Buonconvento. This small village has a vibrant historical centre; there’s a church, the town hall, some museums, and a variety of restaurants and cafes on Via Soccini. This fortified city was once a place of trade and commercial activities, which is how it got its name; Buonconvento means “happy place.” Now it is a quiet little city that enjoys inviting in tourists to learn about its rich history.

Montalcino is considered “the birthplace of Tuscany’s fullest, richest wine: the long-aging Brunello di Montalcino.” Visiting this town is like stepping into a fairytale. Little has changed here since the 16th century, and it remains nestled within the Val d’Orica Natural Park. Fortified walls surround the town, leading up to a castle that towers high into the sky. While you are here, you must sample the famous red Brunello wine.

Castelnuovo dell’ Abate

This small medieval village is closer to a hamlet than anything else. It lies within the borders of Montalcino and was once a fortress of the Abbey of Sant’Antimo. Here you can visit the Romanesque parish church of Saints Philip and James which has preserved some of its 16th century frescos, as well as the Palazzo Bellanti.

Abbey of Sant’ Antimo

This 12th century abbey was built in a Romanesque style and has stood the test of time. It is said that Charles the Great founded the abbey in 781 after his soldiers were afflicted with some kind of unknown illness. Legend has it that an angel appeared before them, offering guidance on a cure. In gratitude to this kind angel, the king decided to build the church to demonstrate his appreciation. Surrounding the grounds are beautiful views of vineyards, olive groves, rolling hills, and wheat fields, making it a perfect location to stop and rest.

Bagno Vignoni

A private transfer will take you into the Roman spa town of Bagno Vignoni. Instead of a traditional town square, Bagno Vignoni sports a pool in the centre of its village where hot water bubbles up from a natural spring. Although you can’t take a dip in the main square pool, there is a spring that you can enter for free at the Parco dei Mulini. Relax as the therapeutic waters work their magic.

Vignoni Alto

Just uphill from Bagno Vignoni is the tiny village of Vignoni Alto. Entering this village is like stepping back in time into a medieval village. A gorgeous chapel, flower-filled gardens, and an 11th century castle are all waiting for you here. Appreciate the old-world beauty as you wander through the village. Make sure to think about what life would have been like when this village was bustling with activity.

San Quirico d’Orcia

Located at a central position between Pienza, Montalcino, and Montepulciano, San Quirico d’Orcia is an ideal destination to use as a home base while exploring the Chianti region; it was also a vital stop along ancient pilgrimage routes on the Via Francigena. Enjoy the lovely churches, visit the gorgeous plaza, wander through the Horti Leonini gardens, and taste the delicious food that Tuscany has to offer.

Known as the “ideal city of the Renaissance,” this city was formed by Enea Silvio Piccolomini who later became Pope Pius II. Built quickly, this city was designed to be elegant and harmonious. Here you can find the Cattedrale dell’Assunta which holds work from many famous painters, the bell tower that commands attention, and a beautiful hanging garden just off the central plaza. There are endless architectural wonders to explore and many charming shops just waiting for you to discover them.

Montepulciano

You may recognise this town from the Twilight movie sequel New Moon, but this charming place is much more than just the setting for a vampire movie. This medieval hilltop town is filled with Renaissance palaces, features an inspiring tower, and (most importantly) is home to the internationally known Vino Nobile, one of the top Tuscan wines. Walking through town is the best way to visit every hidden nook and cranny that you might find interesting.

Piazza Grande

The Piazza Grande is the heart of Montepulciano and is one of the few flat areas in this slope-filled city. In this ancient square, you will find the beautiful town hall with its striking tower, bearing a close resemblance to the Palazzo Vecchio in Florence. At the top of the tower, you can experience panoramic views of the Tuscan countryside. In the plaza, you will also find the rough façade of the Duomo and the fancy Il Pozzo dei Grifi e dei Leoni fountain. The contrasting styles and levels of elegance give the plaza an odd but exciting appearance. In the evening, it’s worth strolling out to the edge of the old town to see the sunset over the Val d’Orcia.

After a private transfer, you will have the ability to explore the busy little town of Greve. This town was once caught between the duelling city-states of Florence and Siena, but now it is the epitome of peaceful small-town life. Wine is for sale around every corner and there are many boutique shops to peruse. The strangely shaped town square is where all the action happens, with plenty of churches and museums to explore nearby; one in particular that you must see is the Wine Museum.

Montefioralle

Just above the small town of Greve is the village of Montefioralle. Montefioralle is one of the oldest and most stunning villages in the Chianti Region. During the Middle Ages, Montefioralle was once one of the greatest military centres of the area. Even to this day, it’s still surrounded by defensive walls. With stone houses, old-style streets, and ancient towers, it’s no surprise that this charming little town dates all the way back to 1085. At the top of the village is the church of Saint Stefano, which is well worth the climb to see.

Via Francigena

Long ago, pilgrims would make their way south to pray at the tomb of St. Peter and Paul in Rome. Unfortunately for them, they didn’t have Google Maps to guide them on how to get there. Despite this, many followed the same road: Via Francigena. This road starts in Canterbury, England and ends in St Peter’s Square in Rome. Via Francigena passes through the Chianti region, so you will have the opportunity to walk along this path taken by pilgrims for centuries.

Monteroni d’Arbia

Sitting along the Via Francigena is the beautiful mountain village of Monteroni d’Arbia. Surrounded by olive groves and fields of sunflowers, this little village feels like something out of a movie. Unlike the surrounding cities, which are known for their culture and art, Monteroni d’Arbia’s historical significance was primarily agricultural. It was home to many farming families and remnants of their old practices are still visible today.

Montefollonico

This tiny hamlet’s foundation dates all the way back to the year 1000, but newly discovered artefacts suggest that there were settlements here much earlier. For years, this tiny town was known for “follatura” (the working and dyeing of wool) and its peaceful serenity. While the wool working is less apparent now, this location is still known for its relaxed vibe. You can visit the Church of San Leonardo, the Church of San Bartolomeo, and the Palazzo della Giustizia while passing through.

Volterra was one of the twelve main towns of the Etruscan confederation at the end of the 4th century. Even though Volterra fell under Roman control, its peculiar city layout still holds true to the original Etruscan style. You can see it for yourself at the remaining sections of the protective walls, the two gates that allow passage into the city, and the Acropolis. What makes Volterra famous worldwide is its hand-made alabaster objects, which are perfect for souvenirs or gifts.

Castelvecchio Nature Reserve

Just outside of San Gimignano is the Castelvecchio Nature Reserve. Chalky hills, dense shrubland, and rocky walls provide a great environment for a rich diversity of flora and fauna. Peregrine falcons love to spend their winters among those rocky walls. On the far end of the reserve are the ruins of the medieval fortress of Castelvecchio.

San Gimignano

San Gimignano became a UNESCO World Heritage Site in 1990 and is known for its spectacular medieval architecture. The original families built approximately 72 tower-houses to display their extreme power and wealth. Only 14 of these structures remain today. Walk among the ancient streets, visit shops in one of the plazas, traverse through a museum, or even read a book in their public library. There is much to see and do in this precious city, but you must try their saffron and signature white wine, the Vernaccia di San Gimignano.

Colle Di Val d’Elsa

Known for its crystal glass production, Colle Di Val d’Elsa is a fascinating location for visitors from around the world. Colle di Val d’Elsa produces 95% of Italy’s crystal glass, which accounts for 14% of production worldwide. Each month they host a market and glass making show that draws in countless tourists. After the festivities, there is still so much to see. Be sure to check out the local church, the museums, and the sweeping views of the Tuscan countryside.

Monteriggioni

Monteriggioni is considered one of the most incredible walled castles in the Chianti region due to its ageless elegance. It is hard to believe that this beautifully preserved structure was originally built in 1219. The perfect circular perimeter was not an intentional design choice, it actually followed the lay of the land. The village hasn’t changed very much in the past few centuries, undergoing only a couple modifications. Upon entering the main square, you will see the stunning Church of Santa Maria Assunta and thus begin your exploration of this charming village.

non-walking activites

Florence leather market.

Located a little outside the centre of Florence is the famous Florence Leather Market. The streets are filled to the brim with vendors selling their wares. Practically anything you could want to be made out of genuine Italian leather can be found in this market. They also sell colourful scarves, unique trinkets, and souvenirs that are perfect for friends back home. We suggest looking through the entire market before buying anything because there will be duplicates. It’s important to note that the more affordable prices will be on the edge of the market; be wary of knock-offs or poor craftsmanship that sometimes comes with a “great deal.”

Castello di Brolio

Perched on top of a hill just outside of Gaiole is the Castello di Brolio. This incredible castle has been a part of the Ricasoli family since 1141 and was used as a strategic outpost by Florence for centuries. After visiting the gardens and the small museum, you can enjoy a spectacular wine tasting within the castle walls. You will have a great experience learning about this castle’s fascinating journey through history.

Vitaleta Chapel

Take the time to visit one of the most photographed churches in all of Tuscany. This charming little church is perched outside of the village of Vitaleta in the middle of a hill. While the true origins of this tiny church remain a mystery, it was restored by architect Giuseppe Partini in 1184 and is now considered a World Heritage Site by UNESCO. This quaint church is a photographers dream; it is surrounded by a magnificent landscape that makes it effortless to capture its beauty, regardless of the weather or season.

Brunello Museum

The Museum of the Community of Montalcino and Brunello was created to remember the rich history and triumphs of the people who call this region home. Everything from the history of their skills to how they dressed to the simple objects that made up their lives are featured here. These things are on display in order to offer perspective into a time long since past.

Museo del Vino

The Chianti region is world-famous for its exquisite wines, but how much do you really know about the winemaking process? The Wine Museum in Greve demonstrates all of the loving work that goes into creating that delightful bottle of wine you adore each night. At the end of the tour, you will have the opportunity to taste the 200 wines in the museum. Now that’s a tour!

Crystal Museum

Colle Val d’Elsa is the primary producer of crystal glass in Italy and one of the leading producers in the world. This town knows a thing or two about glass, and they share it all with anyone who visits the Crystal Museum. Learn the history of glassmaking along with the details that make it so challenging to master. In the end, you will get to witness the crystal forest and experience all of the emotions that it evokes.

Vineyards and Wineries

The Chianti region is known as one of the best wine producers in the world, and it is here that you must take advantage of the vineyards, wineries, and their tastings. Each location offers a unique experience with incredible wine and service. Some of our favourite spots include Viticcio, the Enoteca del Barone Ricasoli, the Casa del Chianti Classico, and Torre a Cona, just to name a few.

1. Arrive at: Florence

2. arrive at: sienna, 3. arrive at: volterra, 4. depart from: montepulciano, 5. depart from: sienna, 6. more options:, hiking the himalayas 35 years on, what’s the right camino de santiago route for me, larapinta loonies – a poem by auswalker michael gibbs about walking the larapinta trail, nakasendo way trail – by sam ludbey, h is for hiking, kumano kodo pilgrimage trail – overview of the routes, the kumano kodo trail – an ancient japanese pilgrimage, the three capes track – an ultimate guide to hiking, why hiking is a no brainer for life planning, larapinta trail – what is the best time of year to walk.

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Via Francigena in Tuscany (Lucca to Siena)

Via Francigena (St. Francis Way) is an ancient European pilgrim route that connects England and France with Rome (Italy) since medieval times. Nowadays, it is commonly known as one of the most famous long-distance self-guided hiking trails in the world. We have selected a wonderful section of the Italian part of the route for you that starts in Lucca and finishes in Siena. Enjoy the oldest independent walking route in enchanting Tuscany as you advance from one stunningly beautiful town to the next through the beautiful Val d’Elsa. You will soak into the medieval atmosphere of the wonderful villages of Monteriggioni and San Gimignano while enjoying the exquisite local cuisine and wine production. Your final destination Siena and its surrounding landscape will take your breath away.

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• Destination Italy
• Duration 8 Days I Level: 2/3 (of 5)
• What is included Accommodation in 2-3 star hotels and agriturismo with en-suite facilities including breakfast (1x dinner included too on Day 3); Detailed roadbook and map in English (incl. access to GPS tracks); Via Francigena Passport; People and luggage transfer on Day 2 (San Minato train station-Hotel San Miniato); Luggage transfers (days 3 to 7 incl.; 1 piece of luggage per person - up to 20kg); Emergency hotline
• What is not included Drinks and other meals; Entrance charges; tickets for the public transport; drinks and other meals. Possible CITY TAX to be paid in cash on the spot (it varies depending on the city and on the hotel’s category; appr. 1-3 Euro per person per night); Luggage transfer is NOT included on Day 2 as you travel by train from Lucca to San Miniato (but it is included from San Minato train station to your accommodation!)
• Best period April, May, June, July, August, September, October

FROM OUR GALLERY

Self-guided hiking and walking tours along Via Francigena in Tuscany, Italy

Day 1. Arrival in Lucca

Day 2. arrival at san miniato alto, day 3. walk from san miniato alto to gambassi (25km, 6hrs, +780m/-650m), day 4. walk from gambassi to san gimignano (18km, 5,30hrs, +600m/-540m), day 5. walk from san gimignano to gracciano (21km, 6hrs, +220m/-220m), day 6. walk from gracciano to monteriggioni (13 km, 3,30hrs, +130m/-60m), day 7. walk from monteriggioni to siena (20km, 5,30hrs, +230m/-250m), day 8. departure day, tour location.

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• Amalfi Coast
• Cinque Terre
• Tour du Mont Blanc

Walking Holidays Italy

Our walking tours in italy.

Montepulciano to Siena Walking Holidays

Via Francigena Highlights

Walking Holidays in Tuscany and Umbria

Luxury Walking Holidays Tuscany

Chianti Trail Tuscany Walking Tour

Sicily and Egadi Islands Walking Holidays

Cinque Terre Walking Tour

Tour du Mont Blanc Self-Guided

Alta Via 1 Highlights

About Walking Holidays Italy

One lifetime would likely not be enough to discover every treasure of Italy’s extensive and diverse landscape. Between the pristine alpine lands in the north and the Sicilian vasts touched by Mediterranean vegetation in the south are yet several other visit-worthy destinations with their own unique characteristics.

The opportunities for walking in Italy are numerous, from the hidden coves of Cinque Terre to Tuscany’s rolling hills. You can settle on anything, be it a challenging hiking experience or a holiday allowing more leisure — walking tours in Italy are as diverse as it gets.

If you are unsure exactly which location you want to visit and which Italy hiking tours suit your abilities and fitness level, our team is here to assist you . We designed each product bearing in mind that not everybody can tackle large altitude changes daily for several consecutive days.

Therefore, we prepared something for everyone !

As such, anyone can get their chance to discover Italy’s one-of-a-kind culture, including their savory cuisine , antique remains from the Roman times, and stunning architecture . That is one big positive regarding walking holidays — there are no restraints, and you can simply go wherever your feet take you and explore!

You can rest assured that we will take our best care of you on our walking holidays in Italy. Accommodation bookings , itinerary planning, and all other logistical nightmares will be tended to. We will also equip you with GPS tracks for your hikes and offer you 24/7 support during the trip.

Give our tours of walks in Italy a glimpse and see which one keeps you intrigued. A hike in the Dolomites ? Or maybe a getaway to the magical Amalfi Coast ? Let us know , and we will help you with the organization.

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Trusted by many, handpicked adventures, unbeatable support, things to know.

Our tours are designed to cater to a broad range of people, but some days can be quite challenging, with long distances and significant elevation gain. We aim to minimize this as much as possible while ensuring a high-quality experience. To fully enjoy our tours, you should be accustomed to walking for 4-6 hours, overcoming around 600 meters of elevation gain.

However, Alta Via 1 hut-to-hut hikes and Tour du Mont Blanc are more demanding and require a higher fitness level. On these tours, you may need to hike up to 8 hours per day and tackle substantial elevation gain.

Yes, our hiking holidays are appropriate for children who are physically prepared and have a good balance. However, to guarantee the safety and enjoyment of our young participants, we suggest that they should be at least eight years old to join our tours.

Proper footwear is crucial for our walking tours. We recommend wearing sturdy hiking shoes with ankle support for all our hikes. The terrain can be uneven, rocky, and slippery. Wearing sneakers can be dangerous, especially if you are not accustomed to hiking on such surfaces, as they do not offer enough protection and support. Robust shoes also provide the necessary support when your legs get tired during long hikes.

Yes, we highly recommend booking in advance to secure your spot. The earlier you book, the better the chances are of getting your preferred options. If you book close to the start of the season or during the season, we may not be able to guarantee availability in the hotels and apartments. Therefore, it is best to make reservations as soon as possible to avoid any inconvenience.

It is essential to note that accommodations at the destinations of our walking tours are in high demand during the summer season. Therefore, early booking is crucial to secure your preferred type of housing. However, we assure you that we will always try our best to provide you with the most suitable lodging based on your preferences. Rest assured that we will do everything possible to ensure that your stay is comfortable and enjoyable.

Our tours are well-organized, and all the destinations are easily accessible and straightforward to navigate. Therefore, it is unlikely that you will require a guide. Our comprehensive handout will provide you with all the essential information while still allowing you the freedom of a self-guided holiday.

However, if you prefer to have a guide, please let us know , and we will make the necessary arrangements for you.

Most of the accommodations we provide offer vegetarian and vegan options for breakfast. Additionally, you will find no shortage of vegetarian and vegan menus in restaurants during the tour. However, it is worth noting that some mountain huts on Alta Via 1 or Tour du Mont Blanc may not offer vegan meals. In such situations, it is advisable to bring your own food to ensure that your dietary needs are met.

The best time to go on a walking holiday in Italy varies depending on the location you plan to visit. Destinations such as the Amalfi Coast, Cinque Terre, and Sicily are best visited during early spring and fall when the weather is pleasant, and the crowds are fewer.

However, in areas like the Dolomites or around Mont Blanc, hiking is not possible when there is snow high up in the mountains. Therefore, the hiking season in these areas is limited from late June to late September. It is advisable to plan your trip accordingly to get the best out of your walking holiday in Italy.

We can best advise you after receiving a filled-out inquiry form .

While hiking in light rain is manageable, it is important to note that hiking during a storm can be dangerous. It is advisable to schedule hikes early in the day during the summer months to avoid thunderstorms. However, if the weather forecast predicts severe weather, it is best to reschedule your walk for another day or explore different tour options.

Your safety is our top priority, and we will always work with you to find a suitable solution in case of inclement weather.

Most of the destinations for our walking tours in Italy have excellent public transportation. While renting a car can provide flexibility, several locations cannot be comfortably accessed by car. Instead, we suggest relying on public transport to reduce stress and have a more environmentally friendly experience.

We provide all the necessary information for buses, trains, and ferries to ensure that you can reach your destination with ease. By using public transport, we can also reduce our carbon footprint and contribute to a more sustainable travel experience.

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Fearlessly Italy

10 Best Hiking Tours in Italy – Book The Adventure Of A Lifetime

An active holiday among the mesmerizing Italian mountain ranges, glacier lakes and picturesque villages sounds like a perfect way to reset from the busy every-day routine. Just imagine yourself breathing that fresh mountain air and savoring the luscious Italian cuisine while sipping the high-quality local wine. This dream-like vacation can become a reality the moment you decide to book one of these fantastic hiking tours in Italy.

When going on these hikes with an experienced guide, your safety is nothing to be worried about because you will always be in the safe hands of someone who passed these trails hundreds of times. Nonetheless, of course, this doesn’t exclude the necessary caution each hiker has to have.

In this article, we offer you an overview of the 12 best hiking tours in Italy that could potentially change your life for the better. From easy gourmet hikes combined with wine tasting to Mont Blanc trekking and volcano exploring – we are confident you will find something that sparks your adventurous spirit.

Table of Contents

Best Guided Walking Holidays In Italy

Walking in tuscany by exodus travels.

The walking tour in Tuscany will take your breath away, so get excited about your upcoming adventure. This might even become your favorite hiking vacation in Italy as you will observe the scenery of the lakeside villages, Italian National parks and Alpi Apuane and Apennine mountain ranges.

The hike starts in Pontecosi and leads through the Orecchiella National Park to the flat summit of Pania di Corfino offering a panoramic view. Alpi Apuane National Park will bring you to astonishing Pania della Croce and the Omo Morto range. Visit the medieval market town Castiglione di Garfagnana and wander through the village of Campocatino. The final destination of the tour is to reach Tuscany’s highest peak of Monte Prado.

This northern Italy tour includes accommodation in the Agriturismo Braccicorti Farmhouse, meals with vegan and vegetarian options and transportation. Also, the hiking guide is always with you during the trek.

After soaking in the beauty and tradition Tuscany is so famous and cherished for, if you can stay a little longer in Italy, try to spend at least 24 hours or even two days in Florence to explore the art and history of this amazing city.

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Amalfi Coast: Hike & Kayak By Intrepid Travel

This hike on the Amalfi Coast gives you spectacular landscapes of Mediterranean treasures that you notice every step of the way. Explore the ancient town of Pompei settled near Naples, follow the Path of the Gods, discover the hidden Valley of the Mills and paddle along the remarkable Amalfi Coast.

Start walking in Naples and continue to the Vesuvius, a famous volcano that erupted back in 79 AD. Arrive in Agerola and gaze into the mountains of Cilento National Park. You will get to know the island of Capri in depth, which was known as the holiday destination for the Roman emperors. From your hotel in Amalfi, continue to the Valley of the Dragon up to Ravello, an unavoidable coastal point.

Delicious breakfasts every morning, transportation and accommodation are all included in the tour’s rate. Activities such as kayaking, a boat cruise and a guided hike along Vesuvius’ Crater are also part of the package.

Gastronomic Barolo Self-Guided Walk By Exodus Travels

This 9-day Gastronomic Barolo self-guided hiking tour in Italy brings closer this peaceful Langhe region of Piedmont in the north-western part of Italy. The gastronomical options are countless; enjoy the wine tasting in Grinzane Cavour or La Morra or satisfy your tastebuds with the specialties served in the Michelin-starred restaurants. If you choose to, you can walk to the Monforte D’Alba, where you can even have an overlook of Mont Blanc on a clear sunny day!

Inscribed in the UNESCO World Heritage list, this region will blow your mind with its countryside full of vines and sunflowers. You can follow a route beside the crystal Tanaro River passing the enchanting oak forest. After crossing the Talloria River, climb up to reach Serralunga d’Alba with its impressive 13th-century castle. In the Talloria Valley, you will find a 16th-century castle of Barolo.

This self-guided tour of Piedmont’s Langhe region offers 8-nights accommodation, transport, meals, route notes and maps. The meals include not just breakfasts but also Italian specialty dishes.

If you can afford some more time in Italy after your tour ends, don’t miss out on the capital of this beautiful region, the royal city of Turin .

Cinque Terre: Hike, Bike & Kayak By Intrepid Travel

The indescribable appeal that Cinque Terre has is undoubtedly best absorbed by hike, bike or kayak – exactly how this Italian tour suggests. The pastel green, yellow, rose, and orange colors radiate from this surreal Italian region, formerly known as the first Italian National Park. It is almost as if the sky dances with the houses’ vivid colors and reflects this beauty to the sea surface.

The first of five villages that make up Cinque Terre is Monterosso, from which you will start your unforgettable hike. Through the famous coastal walk that connects the five villages, you will simply be astonished by the beauty of the vineyard covers combined with occasional forest and citrus groves. When arriving in Portovenere, prepare for the most challenging, yet most rewarding hike of the tour. Hiking in Santa Margherita and kayaking in the Portofino Peninsula come as the cherry on top of this fabulous hiking tour in Italy.

The tour includes breakfast, transport and accommodation, along with many exciting activities.

Italian Lakes: Hike, Bike & Kayak By Intrepid Travel

The northern part of Italy holds precious natural scenery that deserves your full attention. From the clear waters of Lake Como and the surrounding villages to hiking near Lake Garda, this combined tour indeed falls under some of the best hiking tours in Italy. After all the hiking, biking and kayaking, you will probably fancy a real Italian specialty. Your dreams will come true in an instant as you have many high-quality restaurants at your hands.

Absorb the tranquility of the waters surrounding you while you begin your Italian adventure around Lake Como. Try kayaking to arrive at Bellagio, the so-called “pearl of the lake”. The next stop is unspoiled Lake Garda located between the three regions of Lombardia, Veneto and Trentino Alto Adige . During this hike, you can do a bike ride and a boat trip across the lake. Punta Vigilio & Torri del Benaco hike is your next challenge, after which you can relax by the lake.

This guided walk and a favorite bike tour in Italy includes breakfasts, transportation with train, boat, kayak, bicycle and accommodation throughout the trip. Activities like kayaking and boat trips are also part of the price.

Tuscany Walks & Chianti Wine By Exodus Travels

This walking and wine tour combined every gourmet traveler’s favorite activities; hiking and wine tasting, a mix of physical activity and indulgence that is often a favorite by those looking for an adults only vacation . Let Southern Tuscany seduce you with its dreamy landscape, charming sites and flavorsome dishes. On this hiking trip, you will visit the medieval town San Gimignano, Greve’s market in Chianti, the UNESCO World Heritage Site of Siena and the majestic city of Florence .

From Castellina in Chianti, explore the hilltop village of Montefioralle. Absorb the relaxing vibe of Tuscany while learning about wines at the Wine School of Siena. Get lost in Florence, the birthplace of the Italian Renaissance, full of historical sites and attractions. From San Gimignano, visit the Palazzo Comunale, Pinacoteca and Torre Grossa.

Accommodation includes seven nights in a beautiful farmhouse with a panoramic swimming pool. You are also provided with meals, wine tasting, a tour guide, many guided walks and transportation.

Walking in Sardinia By Exodus Travels

A week of dreamlike beaches, inviting crystal clear sea, out-of-this-world cuisine, and rocky mountain views portrays this walking tour in Sardinia. Even only after visualizing these scenes, it becomes apparent why Sardinia is so popular among tourists from all over the world.

Begin the tour of your dreams with a 5-hour hike to Monte Tului, residing at 916m above sea level. See Italy’s deepest canyon, the Gorropu Gorge – also known as the “Grand Canyon of Europe”. Explore the site of the Serra Orrios, one of the most important of the Nuraghe villages. Wander through the archaeological sites of the Dorgali area, after which you will arrive at the still mysterious Nuragic village of Tiscali. Enjoy the Cala Luna, one of the most impressive Mediterranean beaches.

Accommodation, meals with vegan and vegetarian options, transport, and an experienced guide are all part of the tour. The tour also includes treks and many other activities.

Walking in Puglia & Matera By Exodus Travels

Settled between the Adriatic and Ionian seas, Puglia and Basilicata illuminate the Mediterranean’s center like real natural pearls. The vineyards and olive groves, traditional dry-wall construction called trulli characteristic of Itria valley, and not to forget the unparalleled local dishes, make this part of Italy a remarkable vacation destination.

Known for its high-quality white wine and local winery, Locorotondo is arguably one of Italy’s most beautiful villages. Explore the whitewashed houses in Ostuni and spoil yourself with a gourmet dinner in Masseria. Choose between the charming baroque city of Lecce, called the “Florence of the South”, or the striking town of Polignano a Mare. Your hotel will be located in the heart of Matera Sassi, noted for its cave areas. Enjoy the lively nature with many butterflies, orchids, almond and olive trees surrounding you on your hike to the edges of Matera.

Your guide will follow you along on this guided tour. You also have accommodation, meals and transport with all the activities included.

The Dolomites Walking and Hiking Tour By Caspin Journeys

Reach the northern part of the Italian Alps and start your adventure throughout this striking mountain range. The Dolomites , located in Trentino Alto Adige and Veneto, mostly in the Belluno province, offer an ideal hike full of panoramic views and are some of the best adventurous bucket list destinations . After each day, you can relax with the best local meals and share your experience with fellow hikers.

This tour starts and ends in the beautiful Bolzano and will take you to places such as Alpe di Suisi, the unreal flower-filled Braies Valley and the majestic Lago di Braies, one of the glacial lakes that reflect the stunning mountain ranges on the surface. The unforgettable walk beneath the popular “Three Chimneys”, or “Tre Cime di Lavaredo” awaits on the 5th day of the tour. Enjoy an open-air museum with a memory of the First World War in Monte Piana.

The tour includes meals, accommodation, a trekking guide, local transport, and additional services such as bottles of water and entrance fees.

Trekking Mont Blanc By G Adventures

Trekking Mont Blanc includes hiking through the hypnotizing mountain ranges of the Alps in France, Italy and Switzerland. Prepare yourself to reach the thin air in the mountain peaks so you can fully absorb each moment of this fantastic walking tour.

From your hotel in Chamonix, France, begin your journey to Les Houches and experience a 24km (14 mi) hike through the astonishing Les Contamines. After arriving in the Croix du Bonhomme, take a break and have a nice lunch enjoying the views. From the glacier lakes in Les Chapieux, go down to the wonderful Val Veny Valley. Enjoy your free day in the mountain town of Courmayeur, after which you go on to the Swiss mountain village of La Fouly.

Accommodation in the hotels and mountain refugees, as well as the meals, transportation and the experienced guide, are all part of the package price.

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Save on Summer! Use code SUMMER24 for $200 USD ($250 CAD) off trips starting June, July, & August 2024

Booking self-guided travel with Macs Adventure offers you flexibility, ease, and adventure.

We might be biased, but self-guided travel is one of the best ways to experience the world. It’s active travel, led by you. It’s all the best bits of adventuring on your own plus support from a professional team that handles all of your logistics and knows all the local secrets. 

If you’ve never tried a self-guided hiking or self-guided biking trip, here’s what you need to know about how it works, and who it’s best for.

How Does Self-guided Travel Work?

On a guided trip, you’d join a group for a set itinerary, led by someone else who sets your departure times, detours, lunch breaks, and pace. On a self-guided walking or cycling tour, however, we’ll plan your adventure and then you’ll take the lead for a self-paced, individualized journey. 

We handle all the logistics, from booking unique, hand-picked accommodations with inns, bed & breakfasts, or hotels to transferring your luggage between them, so you only need a daypack for hiking or biking. Our app has maps with detailed information about points of interest between your start and end points each day, so you won’t miss any of the scenic or historic detours that elevate your experience. 

All you have to do is select which trip you’d like to go on, and we’ll handle the rest.

Why Choose Self-guided?

The biggest benefits of booking self-directed adventure are: 

A unique, tried-and-tested journey that’s completely your own

Choice and flexibility to travel at your own pace

Expert recommendations 

We’ve been planning self-guided hiking and biking tours for decades, and we’ve developed hand-crafted adventures in places we know well. Our app offers local insights and accurate, easy navigation for each route, and our network of partners is tried and true. We know many of the best places to stay along every trail we serve, and most of these places are small, family-owned businesses that don’t work with online booking platforms. That means we can save you hours—if not days—of research by booking all your accommodations for you, which gives you more time to train for your trip and enjoy when you get there. 

We’re also doing our best to help you travel more responsibly. We prioritize working with local businesses that operate with the environment in mind. You can check out our inaugural impact report  as we pursue B Corp certification. 

Many of our partners have been hosting Macs adventurers for years, which helps us ensure you have a quality stay with hosts who understand the small details of what an active traveler needs. You’ll generally find it easy to arrange a packed lunch, for example, and we make sure your stay comes with a hearty breakfast to fuel your day on the trail. 

If something doesn’t quite go to plan, you’ve got someone looking out for you on the ground. Our partners know to call us if you haven’t checked in by a certain time, so we’ll be proactively looking out for you — great peace of mind. And if you ever need us, we’re just a phone call away. 

Who Should Do Self-guided Travel?

Self-guided travel is great for almost everyone. At Macs, we serve walkers, hikers, and bikers who are active and independent travelers. Here are a few types of people especially well-suited to our trips:

• Couples who love hiking or biking: Traveling in a pair with a partner or friend is the most economical way to book. You can book a room with one bed, a room with two beds, or separate rooms entirely. Whether you’re looking to hike , bike , or take a self-led road trip, we’ll handle all the logistics for both of you so you can focus on prepping for the adventure.
• Small groups: If you’re traveling with a few friends or family members, having help with booking and planning can go a long way. With a self-guided tour booked by Macs, you can outsource all the decision-making to us, and each individual or couple can book and pay separately so that one person doesn’t have to carry all the deposits for hotels.  
• Solo travelers : Whether you’re a seasoned pro or traveling alone for the first time, booking through Macs gives you peace of mind that you’ll be staying in comfortable, safe places, and that someone is looking out for you. If you don’t arrive at your accommodation by the expected time, our partners will contact us so we can make sure you’re alright.

What Type of Self-Guided Trips Can I Do?

At Macs, we focus on walking, hiking, and biking from town to town, self-drive road trips to hike in gorgeous places, and rail and hike trips so you can cover more ground on public transportation. 

Our trip types include:

Classic Routes : From Ireland’s Dingle Way to the Mountains & Lakes of Slovenia’s Julian Alps , our classic routes highlight some of the world’s most beloved journeys.

Slower Adventures : Our Slower Adventures maximize your time to explore. You’ll enjoy shorter distances each day, so you have more free time to visit museums, vineyards, cafes, or even learn how to make cheese in a Swiss Alpine village.

Pilgrimages : Across the world, pilgrimages are often rooted in ancient tradition, and offer incredible opportunities for growth, relaxation, and meeting other travelers. These trips are some of our longest, ranging from a few days to nearly two months. Our routes include the ever-popular Camino de Santiago in Spain and the lesser-known (and underrated) Via Francigena , which winds through Europe from France to the Swiss Alps to Rome. 

In-Style : If you’re looking for something truly special, In-Style trips are built to impress. We’ve scouted the most stylish boutique hotels , Italian agriturismos , French chateaux , grand British estates , eco beach retreats, and other unique accommodations across the world. These trips may include extras such as dinner at a Michelin-star restaurant. 

Discovery : Our Discovery trips give you freedom to cover more ground with easy to moderate walking, such as taking two weeks to drive the entire coast of Iceland . You can choose between Drive & Hike , Rail & Hike , or Self Drive road trips , all of which come with suggestions for gorgeous trails, scenic detours, and personal recommendations for how to spend your days. And of course, we’ll handle all your accommodations. 

Start Your Self-Guided Journey Today

Self-guided adventure combines all the best elements of solo exploration and DIY travel. Get started by exploring our destinations to find your perfect adventure—booked by us, led by you.

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