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Hiking Tours in Tuscany

• Hike through iconic hilltop towns and villages
• Enjoy lazy lunches of fresh organic produce, olive oil, pasta, cheeses & wines
• Visit Renaissance-era Florence, famous for the the Uffizi Gallery, Pitti Palace, and piazza cafés
• Explore Siena, a UNESCO World Heritage site with its Il Campo central piazza
• Wind on trails through vineyards, olive groves and cypress-lined rolling hills
• Tour vineyards and taste local wines at the end of a day on the trail

Discover the tastes and textures of Tuscany, enjoying the almost geometric landscape of hills, 14th-century castles, vineyards and olive trees. Days spent walking through the breathtaking, pastoral Tuscan landscape between quaint towns and past monasteries is a magical experience.

While walking in Tuscany, sample the delicious food and wine for which Tuscany is renowned. Visit Michelangelo’s David and the medieval bridge, Ponte Vecchio over the Arno River in historic Florence on our  Florence to Siena  tour. Or choose to experience the cobbled streets, perched dwellings and exquisite hotels of Tuscany's classic hill towns on our Tuscany: Chianti in Luxury   tour. Whatever interests you, bask in the picture-perfect Tuscany of your dreams.

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Hiking & Trekking Tours & Trips in Tuscany

Hiking and trekking in Italy is rewarding, exhilarating, and, of course, delicious! Find adventures to Tuscany , Florence, Siena, and more on TourRadar.

14 hiking & trekking Tuscany tours with 209 positive reviews

• Hiking & Trekking
• Wine tasting

Tuscany Walks & Chianti Wines

This was the best group tour I've taken with a great mix of activities and down time. Also simply fab and idyllic scenery and Liz was a great tour leader

Picturesque Tuscany

• Book With Flexibility This operator allows you to rebook your dates or tours with them for free, waiving change fees.

A Taste of Tuscany Self-Guided Walking

• Self Guided Walking Holidays

Tuscany Coastal Tour: Pisa & Elba

Tuscany Walking and Wine

One of the best vacations we have ever taken. The scenery was stunning and it was very well organized. Matteo was an amazing guide and handled every details to perfection. The walking can be challenging for portions of the tour, but all very doable if you are in descent shape. You can't beat the scenery you experience! I would highly recommend the tour and will look to do similar tours in the future.

• 10% deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Tuscany Walking & Hiking Tour

• Coastal Walks

Cinque Terre & Tuscany Walking & Hiking Tour

My wife and I talked about going to Italy for 25 years. When we finally decided to go I saw Caspin Journeys on tour radar. It looked the perfect fit for us , and it truly was. Exploring the sites and walking the Tuscany countryside was like a romantic movie for us.

Walking in Tuscany

Walks were really good, and Sara an excellent guide. Weather was not all you could hope for, but that is out of anybody's control

Volterra to San Gimignano Walk

Ryder Cup Golf Tour Italy

Tuscany: hilltop towns of Val d’Orcia & Siena (Self-guided Walking Tour)

Nice tour. Well organized. The Tuscan towns are amazing. We got a hire car right after the tour, and explored other towns and villages. June is a bit too warm, so maybe we should have planned to travel earlier in spring.

Walking Trails of Hidden Tuscany

An excellent trip that introduced us to a new part of Tuscany. The walks were amazing and we would never have found/done them on our own, while the agriturismo stay was really special. The trip exemplified the value added of an Explore tour. Thank you!

Tuscan Coast - In the Footsteps of the Etruscans from Pisa to Elba (8 days)

Under the Tuscan sun - from Siena to Cortona (7 days)

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Tuscany Walking Holidays

Tuscany Walking Tours

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.

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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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Tuscany Hiking Tours

Tuscany hiking tours offer breathtaking views across rolling hills, vineyards, and medieval towns, creating an unforgettable adventure travel experience. From the historic Via Francigena to the rugged paths of the Apuan Alps, planning a hiking tour in Tuscany provides an enriching blend of culture and nature. These treks through Tuscany will immerse you in natural beauty and cultural richness, presenting both challenging and leisurely routes.

Take the first step towards a private travel experience, customized just for you.

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Displaying 12 of 12 tours

St. Francis Way – Chiusi to Città di Castello

During the obscure times of the Middle Ages, an enlightened man walked along the ridges and valleys of the Apennines, looking for God’s signs in nature and talking to people about peace, humility, and togetherness. He was Francis of Assisi, a mystical person who fascinates us still today and whose charisma and philosophy are respected the world over. The St. Francis Way – Chiusi ti Città di Castello Tour is a pilgrimage that follows his footsteps.

Elba Island Walking Tour

The Elba Island Walking Tour is the perfect way to explore all that the “Pearl of Tuscany” has to offer. Trek from alpine villages to the pristine beaches lining the Mediterranean and soak up the rich history of the island in classic fishing villages and vibrant towns.

Via Degli Dei from Bologna to Florence Walking Tour

The Way of the Gods or Via degli Dei is a stunning walking route that connects two of Italy’s most important art cities: Bologna and Florence. Walk through history, with wonderful views over the Italian countryside, wonderful food and wine in each village, and history everywhere.

Via Francigena from Montefiascone to Rome

A journey on the Via Francigena is like traveling back in time, and this self-guided route takes you from Montefiascone to Rome. Walk between lovely historic villages and through scenic Lazio countryside before reaching the incomparable city of Rome. This tour along the Via Francigena combines history, culture, nature, adventure, tradition, and great food into one amazing experience.

Via Francigena from Lucca to Siena

Beauty and adventure await you on this Via Francigena pilgrimage walking tour through Tuscany. Enjoy the best of the Italian countryside as you walk from Lucca to Siena along the ancient pilgrimage route. Panoramic views of rolling hills and vineyard stretch out before you like a painting on this incredible tour.

Walking in Val d’Orcia: Montepulciano to Siena

The Walking in Val d’Orcia: Montepulciano to Siena walking tour is an excellent way to immerse yourself in Tuscany’s most beautiful landscapes and get in touch with Tuscan culture, history, and cuisine through walking and trekking.

From Siena to Cortona Walking Tour

Imagine walking in the Tuscan countryside, connecting the iconic towns of Siena and Cortona. Days filled with walking through Tuscany, evenings in towns and villages, enjoying world class food, wonderful wine, and incredible history. This Siena to Cortona walking tour is the trip for you.

Etruscan Hilltop Towns of Italy Tour

The Etruscan Hilltop Towns of Italy tour is a perfect experience for those who want to get in touch with some of Italy’s quiet, idyllic regions: Tuscany, Umbria, and Lazio. There is something about hilltop towns that makes them look straight out of a fairytale. Perched on top of hills and cliffs, they dominate the surrounding countryside with their castles, fortresses and houses.

Via Francigena: Orvieto to Rome

The Via Francigena walking tour from Orvieto to Rome Tour is a unique opportunity to walk and trek across an ancient pilgrim trail through the awe-inspiring landscape and historic villages before arriving in Rome, one of Italy’s most popular destinations.

St. Francis Way – Firenze to La Verna Tour

During the Middle Age, an enlightened man walked along the ridges and valleys of the Apennines, looking for God’s signs in nature and talking to people about peace, humility, and togetherness. He was Francis of Assisi, a curious person who fascinates people today and whose charisma and philosophy are respected the world over.

Walking in Chianti Tour

This Tuscan walking tour takes you through the enchanting Chianti Region. This is a great way to explore Tuscany on foot, while tasting the world-renowned offerings of the region, including signature Chianti wine and Florentine cuisine.

Hiking the Hiking the Tuscan Coast from Pisa to Elba

Want to see a different part of Tuscany from what you expect? Trade the rolling hills for the stunning coastline on this wonderful walking tour. Fear not, even though you are on the coast you will still indulge every meal with wonderful Tuscan food and wine, a great reward after a beautiful day walking.

1-12 of 12 tours

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Tuscany General Information

Where to trek in tuscany.

When planning where to trek in Tuscany, you have numerous enchanting routes and hubs from which to choose. Siena and Florence serve as excellent starting points for trails like the Via Francigena . For more rugged adventures, the Garfagnana region offers mountainous landscapes and remote trails.

What makes Trekking in Tuscany special?

Trekking in Tuscany is a special experience due to the stunning combination of natural landscapes and historical settings. The region features well-trodden paths like the Via Francigena that connect ancient towns and cities through picturesque countryside, offering trekkers a unique journey through time and nature.

When to go Trekking in Tuscany

The best times to go trekking in Tuscany are during the spring (April to June) and autumn (September to November). These months offer mild weather, fewer tourists, and vibrant natural scenery. Summer provides warm weather but can be very hot for strenuous activities, while winter may see some trails less accessible due to rain.

Top 5 Treks in Tuscany

• Via Francigena - This ancient pilgrim route runs from the north to the south of Tuscany, passing through enchanting medieval towns like San Gimignano and Lucca. It's a historic path that offers a taste of Tuscany's rich heritage and beautiful rural landscapes.
• Apuan Alps - For those seeking a more challenging hike, the Apuan Alps offer rugged trails with stunning views of both the mountains and the sea. This area is less traveled and provides a unique glimpse into the natural diversity of Tuscany.
• Chianti Countryside - Walking through the Chianti region allows trekkers to explore the heart of Tuscany’s wine country, with trails winding through vineyards and olive groves, connecting quaint villages where wine tasting is a must.
• Tuscan Archipelago National Park - Located on the islands off the Tuscan coast, such as Elba, this national park offers coastal hikes with spectacular sea views and pristine natural environments, ideal for those looking to combine hiking with some beach time.
• Path of the Gods on the Amalfi Coast - Extending the trekking experience beyond Tuscany, this renowned path offers breathtaking views along the Amalfi Coast. Though not in Tuscany, many visitors to the region extend their adventure to include this iconic southern trail.

Travel tips for Tuscany Hiking Tours

What to pack when trekking in tuscany.

Pack lightweight, breathable clothing for warm months, and layers for cooler times. Include a good pair of hiking boots, a hat, sunscreen, a water bottle, and a rain jacket. Don't forget a camera for the scenic landscapes and binoculars for bird watching.

Are luggage transfers available on treks in Tuscany?

Yes, luggage transfers are available on many organized trekking tours in Tuscany, especially on popular routes like the Via Francigena. This service allows you to hike with just a daypack, making the trek more comfortable.

How long do I need to trek in Tuscany?

The length of your trek depends on your itinerary and the routes you choose. Short treks can last a day or two, while more extensive routes like the full Via Francigena section in Tuscany can take a week or more.

Are there family-friendly treks in Tuscany?

Yes, there are several family-friendly treks in Tuscany, such as those in the Chianti region, which are less strenuous and pass through vineyards and medieval towns. These routes offer activities and sights that engage both children and adults.

What are the accommodations when trekking in Tuscany?

Accommodations range from rustic farmhouses and bed-and-breakfasts to luxury hotels and traditional agriturismos, which provide a more authentic Tuscan experience. Many trekking paths have accommodations along the route suited for different budgets and preferences.

Can I do a self-guided trek in Tuscany?

Yes, self-guided treks are very popular in Tuscany. Well-marked trails like the Via Francigena are suited for those who prefer to explore at their own pace. Maps and apps are available to help with navigation.

Can I do a guided trek in Tuscany?

Guided treks are available and are a great way to gain deeper insights into the region's history, culture, and nature. Guides can enhance your experience by sharing local knowledge and handling logistical aspects.

What is the best season for trekking in Tuscany?

The best seasons for trekking in Tuscany are spring (April to June) and fall (September to November). These months feature milder weather, fewer tourists, and the natural landscape is at its most vibrant.

What safety precautions should I take when trekking in Tuscany?

Always check weather conditions before heading out and carry a map, compass, or GPS device. Stay hydrated, especially in summer, and be aware of your limits to avoid fatigue.

Are there any permits required for trekking in Tuscany?

No permits are required for trekking in Tuscany. However, some natural reserves and protected areas may have specific rules and regulations, so it's good to check in advance.

What type of wildlife can I expect to see while trekking in Tuscany?

Tuscany's diverse habitats are home to wildlife such as wild boars, deer, porcupines, and a variety of bird species, including peregrine falcons and eagles in some areas.

Is trekking in Tuscany suitable for solo travelers?

Tuscany is a safe and welcoming destination for solo travelers, with friendly locals and well-traveled routes that make solo trekking a pleasant and secure experience.

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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 Cultural Walking Tour

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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. 

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.

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.

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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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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Week of Hiking in the Hidden Parts of Tuscany

June through September

Pisa, Italy is your starting point

Intermediate

Things to know

Not far from bustling piazzas and glistening church interiors, Tuscany hides soaring mountains waiting to be explored by adventurers. Between the limestone Apennines and the marble Apuan Alps lies the unspoilt Tuscan region of Garfagnana that offers a harmonious blend of indulgence and outdoor exploration. Spend a week tracing ancient shepherd trails beside vineyards and olive groves, meandering along dramatic ridges between medieval villages and summiting peaks revealing views that stretch to the coast. Switch it up by strolling through dense chestnut forests, enjoying a picnic by a mountain lake, or exploring the historical sites in the nearby town of Lucca. In the evenings, return to your villa to relax by the pool, unwind in a hot tub and savor delectable Tuscan cuisine and wines on the terrace overlooking the Serchio Valley. Discover the wild heart of Tuscany—where hedonism and hiking go hand in hand.

Traverse mountain ridges, summit peaks, and savor dramatic scenery tamed by vineyards and olive groves

Stay in a luxurious villa atop a valley with a pool and a hot tub

Combine hiking in the wilderness with historical towns and villages and superb Italian dishes

​​Embark on this guided hiking adventure and discover the secret treasures of Garfagnana in Tuscany. This 8-day trip takes you through vineyards, olive groves, and charming villages, but also offers a different and more dramatic experience of this famous Italian region by taking you through its scenic mountains between the Apuan Alps and the Apennines. You’ll stay at a luxurious villa overlooking the serene Serchio Valley, where you can relax by the pool and savor delicious Tuscan cuisine.

You will meet your Tuscany hiking guide at Pisa airport and get transferred to a charming villa nestled in the Tuscan hills, offering breathtaking views of the serene Serchio Valley. After settling into the traditional farmhouse, dinner will be served on the terrace, surrounded by the vineyard. Your guide will provide an informal briefing, answering any questions about the upcoming week. Get to know fellow hikers a bit better over dinner. Meals: Dinner Accommodation: Villa

Start the day with a transfer to Palagnana (757m / 2,484 ft), a quaint hamlet. Embark on a trail through stunning beech woodland, reaching the Foce delle Porchette (980m / 3,215 ft) with magnificent views of the limestone hills and possibly the Mediterranean on a clear day. Ascend along a limestone gorge to the grassy summit of Monte Croce (1314m / 4,311 ft), savoring a relaxing picnic lunch. Descend through beech woodland, passing the charming hamlet of Pioppo, before ending the walk with a well-deserved drink in a local bar. Accommodation: Villa Meals: Breakfast, picnic lunch, and dinner Walking: 5-6 hrs Distance: 9 km (5.6 miles) Altitude gain/loss : 580 m (1,903 ft)

After a short transfer to Corfino (836m / 2,743 ft), journey to the remote village of Pruno. Follow a cobbled mule track through serene beech forests, pausing at the Fonte del Amore (Fountain of Love). Reach the charming 16th-century village of Campaiana (1358m / 4,455 ft) for lunch, then ascend to the long summit plateau of Pania di Corfino (1603m / 5,259 ft). Take in breathtaking views of the jagged peaks of the Apuan Alps. Descend along the well-worn shepherds’ trail, passing Rifugio Isera and returning to Pruno. Accommodation: Villa Meals: Breakfast, picnic lunch, and dinner Walking: 6 hrs Distance: 13 km (8.1 miles) Altitude gain/loss : 775 m (2,543 ft)

Embark on the longest and most rewarding day of the trip, ascending Pania della Croce, the fourth highest peak in the Apuan Alps. Begin at the small chapel of Piglionico (1008m / 3,307 ft) and gradually climb to Rifugio del Freo at Mosceta (1200m / 3,937 ft). Traverse to the Foce di Valli pass (1266m / 4,154 ft) at the base of Pania della Croce. Ascend on a steady zigzag path to the summit ridge, where a well-deserved picnic awaits by the summit cross (1858m / 6,096 ft). Admire breathtaking views of the Tyrrhenian Sea and, on clear days, Corsica. Descend through the “Canale dell Inferno,” crossing alpine meadows and returning to the beech forest. Accommodation: Villa Meals: Breakfast, picnic lunch, and dinner Walking: 8 hours Distance: 12 km (7.5 miles) Altitude gain/loss : 940 m (3,084 ft)

Enjoy a day of tranquility at the villa or explore the surrounding area. Visit the delightful city of Lucca, just 45 minutes away by train, with its medieval walls, splendid piazzas, cobbled streets, and a beautiful basilica. Alternatively, relax by the pool, unwind in one of the garden’s hammocks, or embark on a local walk. Breakfast is included, while lunch and dinner are not, allowing you the freedom to choose where and when to eat. In the evening, consider a leisurely stroll to a local restaurant. Accommodation: Villa Meals: Breakfast

Begin the day with a transfer to the foothills of the Apennines. Commence the walk at Vetricia (1,308m / 4,291 ft), ascending through beech woodland to the open pastures of La Porticciola (1,700m / 5,577 ft). Descend via “Hannibal’s camp” to reach the picturesque Lago Santo (1,501m / 4,925 ft). Undertake a steep climb above the lake to the summit cross. Enjoy lunch at the summit while relishing extensive views across the Apennines. Descend to the historic town of Barga, making sure to stop at the local gelateria for a refreshing treat. Return to Vetricia and transfer back to the villa. Accommodation: Villa Meals: Breakfast, picnic lunch, and dinner Walking: 6-7 hrs Distance: 11 km (6.8 miles) Altitude gain/loss: 930 m (3,051 ft)

Embark on the ascent of Monte Forato, a perfect finale to the week. Begin in the quiet village of Fornovolasco, strolling through cobbled streets. Follow the forest trail to the mountain pass of Foce di Petrosciana, with views of Monte Procinto’s rock tower and the mountain chain leading to the Mediterranean. Ascend to a magnificent limestone archway below the peak of Monte Forato (1,223m / 4,012 ft). A short climb brings you to the summit, offering outstanding views of the Tuscan hills. Enjoy a picnic lunch before continuing along the ridge to the Foce di Valli pass, then descend through alpine meadows to the beech forests. Upon returning to Fornovolasco, indulge in refreshments at the local gelateria in Gallicano. Back at the villa, take a final dip in the pool, relish a delicious local cuisine, and raise a toast to a successful Tuscan adventure. Accommodation: Villa Meals: Breakfast, picnic lunch, and dinner Walking: 6-7 hrs Distance: 10 km (6.2 miles) Altitude gain/loss : 915 m (3,002 ft)

Enjoy a final breakfast on the terrace before transferring to Pisa airport. Say goodbye to your Tuscany hiking guide, fellow hikers, and to Italy—or continue touring on your own. Meals: Breakfast

Meet your guides

For the past five years Cloud 9 has organized a private guided hiking adventure for our family in Europe – including the Alps, the Pyrenees and Tuscany. The trips have been outstanding! Emma and Helen’s attention to detail means everything goes very smoothly with each day of hiking tailor made to our family’s ability. Emma challenges us to go higher, including hiking a 4,000 m peak – but our safety is always paramount. Her knowledge of the area means our itineraries are full of hidden gems – amazing trails off the beaten track and secluded mountain cafes with delicious food.

Our guide was Jason and he did an incredible job. He didn’t make us feel rushed at all and he followed our pace. He also was very educated about the outdoors and sounds like a very experienced hiker/climber. Highly recommend!

What you get on this adventure:

• An experienced, local hiking guide with extensive knowledge of the area
• An 8-day hiking adventure with 5 days of trekking
• Twin-room accommodation in a private villa (7 nights)
• Airport transfers
• Transport during the adventure (apert from optional excursions during the rest day)
• Meals as indicated in the itinerary (most days breakfast, picnic lunch, and dinner are included)

What’s not included:

• Transportation to Pisa
• Meals not indicated in the itinerary
• Travel insurance
• Guide gratuities — optional

This Tuscany guided hiking trip is suitable for hikers with some experience and a reasonable level of fitness. The daily walks will typically be around 5-7 hours on well-marked trails, with ascents ranging from 500 to 1,000 meters (1,640 to 3,280 feet). There will be a couple of longer days when climbing Monte Giovo and Pania della Croce. While it is not necessary to be an expert hiker, being in good physical condition before the trip will enhance your overall enjoyment. We suggest you do some long hilly walks in the weeks before the trip, especially if you have new boots.

Keep in mind that all days on this trip are optional (you can always decide to stay in your villa or go somewhere else) and that the itinerary may be adjusted by the leader based on weather conditions and the group’s ability. In terms of altitude, the maximum reached on this trip is 2,054 meters (6,739 feet) during the Monte Prado climb. Most days, the maximum height reached will be between 1,300 and 1,700 meters (4,265 to 5,577 feet). Since you return to the valley every evening and spend limited time above 1,500 meters (4,920 feet), altitude is not expected to be an issue.

If you’re looking for something that is a bit more challenging, you may like this hiking adventure in the Venetian Alps at the foot of the Dolomites .

Here’s a list of the equipment you need to bring:

• Day pack large enough to carry all the items you might need in a day (around a 20-30L bag)
• Hiking boots or trekking-specific trainers
• Water bottle(s) (2L capacity in total)
• Light waterproof jacket and trousers
• Socks and underwear
• Trekking pants and shorts
• Moisture-wicking T-shirts
• Fleece jacket
• Lightweight warm hat
• Buff — optional
• Light pair of gloves (a mid or light pair of gloves is fine)
• Sun Hat and sunglasses
• Plastic bags / dry sacks
• Basic first aid kit (containing plasters, blister treatment, painkillers, antiseptic cream, and diarrhea treatment)
• Toiletries (bug spray, sunscreen, lip protection, cosmetic products, etc.)
• Walking poles – optional
• Swimwear for the pool
• Camera — optional (but recommended)
• Lightweight sandals and sneakers — optional

Make sure to feel comfortable in the clothes that you bring and don’t forget to take some regular casual clothes as well.

During your guided hiking tour in Tuscany, you’ll stay in a private villa that exudes rustic charm with its Garfagnana stone, chestnut beams, and terracotta tiles. You’ll be able to Indulge in ultimate relaxation as you unwind by the pool, dine on the terrace adorned with wisteria, and gaze upon the serene Serchio valley and vineyards. Immerse yourself in luxury with antique furniture, art, and plush beds, with an inviting sitting room that comes complete with wood-burning stove and a collection of books and games. Apart from that, this Tuscan villa also boasts landscaped gardens with hammocks, a swimming pool, hot tub, and recreational amenities (tennis table, marked badminton court, and a yoga deck). You will sleep in a twin room, but you can also opt for a single room for an additional fee. Each day (apart from the rest day), you’ll get to enjoy breakfast and a 2-course dinner accompanied by fine wines. All food restrictions and dietary preferences can be easily accommodated—just let your guide know in advance!

Group sizes and prices:

• For this group adventure, the maximum client-to-guide ratio is 11:1.
• It takes a minimum of 4 people for this tour to operate.
• The cost does not decrease as the group grows.

Hiking in Tuscany can be arranged for larger and for private groups. Contact us to make arrangements.

Min. age requirements:

• If you are older than 18, you’re good to go.

Pisa is the starting point of this guided hiking trip in Tuscany. To get there, most people fly into Pisa International Airport . Once there, you will meet your guide and fellow hikers for a private transfer to your accommodation near the towns of Barga and Gallicano.

Airport transfer from the airport is usually scheduled at 14.30. If coming later in the afternoon, we suggest you arrive on your own by train. To do this, you first need to get from the airport of the Pisa Central Station and then catch a train for Barga-Gallicano, where your guide will pick you up and take you to the villa.

57hours is committed to providing safe outdoor adventure experiences. We require all guides using our platform to have a COVID-19 safety plan and to make the details of that plan accessible to travelers. In most cases, group sizes will be reduced, guides will avoid overcrowded locations, and other safety measures will be met depending on the location and activity.

We also expect clients to respect local regulations and take measures to protect themselves, guides and the communities they’re traveling to. For more information on COVID-19 measures in Tuscany, Italy, please refer to the Italian Ministry of Health website.

Please contact us if you have any questions or require further information. We are happy to provide you with the most up-to-date information!

A 30% non-refundable deposit to secure your place is due upon booking. The remaining amount is paid 10 weeks (70 days) prior to departure.

Secure your spot for 2025 with a 10% deposit!  This tour gets sold out very quickly, but with early-bird booking, you can rest assured you’ve booked your dream adventure in time.

• Only 10% of the total amount should be paid as a deposit upon booking. This deposit is non-refundable, but can be transferred to another 57hours adventure anytime in case the dates don’t suit you. This can be done by the end of the year.
• Another 20% needs to be paid by the end of this year.
• The remaining balance is due 10 weeks (70 days) prior to departure.

Once the trip is confirmed by the guide, the cancellation policy stated below applies.

• If Client cancels the Booking anytime prior to seventy (70) calendar days in advance of the trip contemplated by the booking, Client’s deposit will be forfeited.
• For cancellations thirty-one (31) to seventy (70) calendar days in advance, Client is entitled to a refund in the amount of fifty percent (50%) of the total price of the trip.
• For cancellations thirty or less days in advance, Client is not entitled to any refund.
• Any reimbursable expenses arising out of the Booking incurred by Guide prior to the date of cancellation (including but not limited to plane tickets, car rental payments, and lodging or transportation fees) are non-refundable as soon as they are incurred by the Guide.

Other things to do in Tuscany

Val d’Orcia Tour: Week of Hiking in Tuscany

Hike and Explore the Wild Heart of Tuscany

View all (53) adventures in Italy

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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]

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 200 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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On-line booking click on one of the two choices below here:

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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

From Medieval Hill Towns to Seaside Villages

Hiking tuscany and the cinque terre.

From $6,695

Call 1-800-368-2794 or contact us for any questions

We bring you to two irresistible Italian realms in full WT style, with stunning hikes each day and expert Trip Leaders who bring this celebrated land to life. Our hikes cross Tuscany's harmonious landscape, discovering terraced vineyards, tiny hamlets, and classic hill towns on our way from San Quirico d'Orcia, once a stop for pilgrims on the Via Francigena, to San Gimignano. After a walk on Lucca's historic walls, we head to Cinque Terre, where five ancient villages nestle on cliffs and along deep coves on the Ligurian Coast. We connect these seaside villages with breathtaking hikes, sample Liguria's fresh-caught seafood, and ferry to Palmaria Island for a final hike with spectacular Cinque Terre panoramas.

Arrive: Florence, Italy

Depart: Pisa, Italy

• Visit the vineyards of Chianti, with a picnic at a family-run winery
• Experience the beauty of the Tuscan towns of San Quirico d'Orcia, Pienza, Siena, and San Gimignano
• Walk the famed coastal trails that connect the five Cinque Terre villages
• Ferry to Palmaria Island for a spectacular hike and coastal views
• Enjoy Trip Leaders who know all the best trails, trattorias, and local delicacies!

Dates & Pricing

Pricing below is per person and based on double occupancy. The earlier you book, the more choice you’ll have. WT also has the most generous cancellation and transfer policies in the industry, we make it easy if you change your mind. Have a small group of your own? Take over an existing date or choose your own. You’ll have your own private guide–and the adventure–all to yourselves!

Payment & Cancel Schedule

$600 due at time of reservation 90 days prior to departure: Balance

Cancellation & Transfer Schedule

Up to 91 days prior to departure: No Charge! 61-90 days prior to departure: 25% of trip cost 46-60 days prior to departure: 50% of trip cost 45 days or less: 100% of trip cost

• Expert leadership of a Wilderness Travel Trip Leader and local guides
• Accommodations in hotels
• All meals included except 4 dinners as indicated in Detailed Itinerary
• A glass of wine or beer with dinner
• All ground transportation and baggage handling from meeting until departure
• All activities as indicated in Detailed Itinerary

Not Included

• Travel to and from the arrival and departure location as indicated in Detailed Itinerary
• Additional hotel nights outside the trip's scheduled dates
• Optional gratuities to Trip Leaders or staff
• Optional travel insurance
• Other expenses of a personal nature (some alcoholic beverages, laundry, etc.)

Accommodations

Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.

Relais Palazzo del Capitano

San Quirico d'Orcia, Italy

Days 1-2 (2 nights)

Hotel Pescille

San Gimignano, Italy

Days 3-4 (2 nights)

Alternate Accomodation: Hotel la Cisterna

Hotel Ilaria

Lucca, Italy

Days 5-6 (2 nights)

Alternate Accomodation: Grand Universe Lucca

Hotel Porto Roca

Monterosso, Italy

Days 7-9 (3 nights)

Trip Leaders

Wilderness Travel Trip Leaders have a passion and a joy for creating an unforgettable journey. We are extremely proud of them and the incredible travel experiences they make possible. For more information, including client comments about them and which specific trips they will be leading, please click on their profiles below.

Giuseppe Aruta

Teresa Baldi

Lisa Halderman

Isabelle Johnson

JoAnn Lantz

Vicky Sotriffer

What the Trip is Like

This trip is rated Level 3, Moderate, according to our trip grading system. While we do not see major elevation gain or loss, you will need to be comfortable hiking up to 6 miles a day and being on your feet for 4-5 hours a day. Trail conditions, weather, and the group's level of fitness can affect hiking times and pacing.

• 500-600 feet gain/loss
• Day 2: 6 miles, 3 hours, 900 feet gain, and 700 feet loss

Client Testimonials

"I was a tour guide myself in my younger years; thus, I feel qualified to address all the fine qualities of this experience. Wonderful human touches brought so much life to this trip: the cozy restaurants, charming hotels, the farms and vineyards, and above all, our three guides—lovely human beings, and so professional. Superb!"

Twin Lakes, CO

"This was a great itinerary that was well organized and well executed. We had great food and wine at every destination and very well-informed trip leaders."

Highland Park, IL

"I LOVED THIS TRIP. As I look back, I have nothing but happy memories of each and every day. Our group was amazing as far as getting along and making new friendships. I have a new love for Italy and the countryside, as well as the traditions and language, all because of this trip and these guides and all the careful prep put into the whole thing. Cannot thank you enough."

Jupiter, FL

"Outstanding trip, thank you! I absolutely loved the hiking and felt like we were seeing off-the-beaten-tourist-track places. Great guides, really good food, and the Italian Riviera was spectacular—especially the last day hiking out of Portofino to the cove with the big seafood lunch on the beach. What a way to end the trip! It was fabulous in every way. This was one of my favorite trips ever, and I've traveled extensively throughout the world. I can't wait to do another one with you."

"I was very impressed with this trip. Our guides were wonderful, and I loved seeing some of the out-of-the-way villages we hiked through. It was great to be off the beaten path."

Methuen, MA

"Our trip was fabulous on every front—we felt very well taken care of."

"This was a well-designed trip which we very much enjoyed. Our Trip Leader JoAnn was well informed, organized and very engaging throughout our trip. We learned a great deal on our hikes and so enjoyed the museum tours and the guides she chose to lead them. We have always spoken highly of WT to our friends and family."

"Excellent lodging at hotels that we would return on our own. Can't say enough about the talents of our leaders in putting together the picnic lunches. This was our first trip of this kind, and I expect we'll be back. Sicily? Dolomites? All in all, it was a great value for the money, and I so appreciated the mix of hiking and in-town visits. "

Jamaica Plain, MA

"I enjoy reliving the beauty of the countryside, the plethora of information received, the charm of the medieval cities, the delicious picnics, and the company of interesting, intelligent, cheerful people—both fellow tour members and the wonderful trip leaders."

Burlingame, CA

"It was an overall wonderful experience—we didn’t have to think about anything (other than what to order for dinner)."

Sudbury, MA

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Book your trip today

Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!

Submit the form below to download itinerary

Trip Download Itin

Trip Levels

With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult—see descriptions below for explanations of each number. A plus (+) sign means the trip is a bit more strenuous than other trips of that level. The detailed explanation of each trip—below the bar with the number rating—is perhaps more important, specifying activities, altitudes, hiking, and travel conditions. The Detailed Itinerary, available by download or mail, gives further information. Our Area Managers can also answer questions and guide you to the trip that best suits your interests.

Level 1 – Easiest

Non-camping journeys, optional walks, little elevation gain or loss.

• Royal Rajasthan and Villages of India
• Small ship cruises

Level 2 – Easy to Moderate

Hotel nights and/or safari-style camping, hikes of two to four hours on some days. Other physical activities are sometimes included, such as optional sea kayaking.

• Our African safaris
• Costa Rica Wildlife

Level 3 – Moderate

Half- to full-day hikes (3-6 hours) over rolling countryside on most days, occasional steep trails. Many of our hotel-based walking tours are in this category, as are our snorkeling adventures.

• Tuscany & the Cinque Terre
• Argentina: Hikes and Estancias of Patagonia
• Palau Snorkeling & Sea Kayaking
• Some trips with minimal hiking but rugged travel conditions or long drives, such as  Tribal Ghana, Togo & Benin,  are Trip Level 3.

Level 4 – Moderate to Strenuous

Full-day hikes (4-6 hours), mountainous terrain, significant elevation gains and losses (hiking up or down as much as 3,000 feet) on many days. Altitudes no greater than about 10,000 feet.

• Ultimate Patagonia
• Hiking the Spanish Pyrenees

Level 5 – Strenuous

Full-day hikes (4-8 hours), mountainous, steep terrain (hiking up or down as much as 3,500 feet) on many days. Trips with hiking at average altitudes of 10,000 to 12,000 feet are in this category.

• Inca Trail to Machu Picchu
• Everest Lodge to Lodge

Level 6 – Very Strenuous

Full-day hikes (5-8 hours), mountainous, steep terrain (hiking up or down as much as 3,500 feet) on many days. Most hikes take place at altitudes above 10,000 feet, with some days ascending as high as 18,000 feet.

• Everest Base Camp
• Climb Kilimanjaro!

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Cinque Terre & Tuscany Walking & Hiking Tour

Small Group Adventures for:

Couples, Friends & Solos Adults 18+ Women's Adventures Women 18+ Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18) Families with Older Teens & 20s Best for ages 17-23 (min. age 14) Families with Teens & Kids Best for ages 9-17 (min. age 4)

From $4,399 - $4,849 /person

Activity Levels 1-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Casual & Casual Plus Hotels

Premiere Hotels - From lavish luxury to on-trend boutique, offering experiences as unique as the regions we explore.

Casual Plus Hotels - A step above Casual but not quite Premiere.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

2024 : May-Oct 2025 : May

Coastal Italy's Seaside Charm & Tuscan Villages

To prepare for this hiking tour in Cinque Terre and Tuscany, learn how to say beautiful in Italian. So you'll know what to say when you admire Cinque Terre’s spectacular views or Tuscany’s gorgeous landscape. It’s the simplest way to describe a journey with your fill of freshly caught seafood, delectable wines, friendly people, warm sunlight, the azure sea, cypress trees and hill towns. Bellissimo .

• Hike Cinque Terre's World Heritage coastline, with brightly colored cliffside villages and unbeatable views of the sea
• Savor seafood on the Mediterranean coast and simple hearty fare with the renowned local wine in Chianti
• Stroll through archetypal Tuscan villages, picturesque vineyards and peaceful tree-lined country lanes
• Delight in the subtleties of crisp Ligurian white wines and full-bodied Tuscan reds at enchanting family-run wineries

End Florence

Do not book flights until your trip details are confirmed.

We recommend flying into Pisa Airport (PSA) and out of Florence Peretola Airport (FLR). You can also fly into Florence or Rome's Leonardo da Vinci-Fiumicino Airport (FCO) and then travel on to Pisa by train.

Please note that trip start and end locations are subject to change and can vary by departure. A Travel Planner, complete with trip details specific to your chosen date, will be sent to you at time of booking or soon after and will be viewable in your Backroads account.

* Start/End locations may vary. Do not book flights until your trip details are confirmed.

Hike across a dramatic landscape to Portovenere, taking in expansive vistas of the Golfo della Spezia • Walk along coastal trails past terraced vineyards and olive groves • Splendid views await at our waterfront hotel • Savor fresh frutti di mare at a seaside restaurant.

Experience Italian warmth and hospitality at this tranquil waterfront hotel, complete with sweeping views of the Golfo Dei Poeti.

Get to know the Cinque Terre’s majestic coastline, a World Heritage site, by hiking and by train • Well-groomed paths lined with ancient stone walls lead from stunning Riomaggiore through cliffside Manarola, quiet Corniglia and vibrant Vernazza to inviting Monterosso al Mare • Pass elegant villas en route to posh Portofino • A walk along Portofino’s postcard-perfect waterfront is a must • Explore Santa Margherita Ligure, the childhood home of Christopher Columbus • Enjoy Mediterranean flavors and dinners by the sea.

Just steps from the bay of Santa Margherita, this art nouveau-style hotel is set atop a promontory, surrounded by oak, pine and palm trees.

Head inland to Chianti's quintessential Tuscan villages, vineyards and cypress-flanked lanes • Hike through the medieval villages of Greve in Chianti and Panzano • Stroll through the narrow streets of the historic ridgetop Radda, the epicenter of Chianti Classico • Walk to 1,000-year-old Castelvecchi wine cellars to enjoy a signature Backroads picnic with a glass of local wine • Soak up grand pastoral panoramas from the strada bianca (white road), surrounded by vineyards and olive groves • Sip regional wines at a fun and informative tasting • Extend your walking tour in Cinque Terre and Tuscany with a visit to Florence, birthplace of the Italian Renaissance and our magnificent gateway city.

Owned by the same family since the 1500s, this former manor house offers vistas of the countryside, olive groves and vineyards of Chianti Classico. (pool)

Our trips range in activity levels from leisurely (1) to avid (5) with plenty of options in between. Several routes are offered each day so you can choose your perfect amount of activity. Learn more

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What's Included

• All breakfasts, 4 lunches, 4 dinners
• Expertise and services of our experienced Trip Leaders
• Snacks and beverages between meals
• Additional guides and experts from the region on many trips
• Van shuttles to support a variety of route options
• Comprehensive Travel Planner with detailed pre-trip information
• Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
• All gratuities at hotels and restaurants
• Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
• On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
• Trailercycles, carriers, and kid-sized helmets for Family Trips
• Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
• Park and other entry fees
• Fares for trains, ferries and other modes of travel as listed in the Travel Planner
• Select coach transfers
• Baggage transfers and porterage

Not Included: Leader gratuities, transportation to and from your Backroads trip start & end locations, and on-your-own meals & activities.

Straight Talk

We want to make sure you're on the trip that's right for you. Every Backroads trip is unique and this one is no exception.

Cinque Terre is a popular tourist destination with busy peak seasons, especially during the summer months and on national holidays. Like any sought-after national park destination and World Heritage site, crowds are common. To access the best hiking areas in the Cinque Terre, we will sometimes be riding on state-operated regional trains alongside locals and other tourists. Like all public transportation, the trains can be subject to delay and may be crowded during peak seasons. Because the national park is still recovering from trail damage from previous years, weather-related trail closures may occur. In the event of a trail closure, your Backroads Trip Leaders will have alternate hikes and activities available.

Our routes through this captivating terrain are a combination of loop hikes and out-and-back trails that begin and end in the same location. In some cases our shuttles will get us to and from the trailheads, but due to the nature of these trails, we usually won't see our vehicles along the route. Ample trail support in the form of water, snacks and encouragement is provided by your Backroads leaders and local guides. 

​Hotel della Baia is a modest property with a picturesque location. While this property is simpler than the typical Backroads standard, we've chosen it because of its proximity to our favorite routes and the fantastic Mediterranean views.

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Hiking Tuscany

Excursions, hiking and cycling in the nature.

Birdwatching

Sezione italiana

Andrea innocenti.

Hiking tour in Tuscany with local guides for your groups on the best hiking tour in Tuscany . Best hikes in Tuscany All our activities are in Tuscany. Consulting, hiking and cycling tours in Tuscany. Tuscany is a region very rich in heritage and natural areas. We love Alpi Apuane (Apuan Alps) , Garfagnana , Chianti , Valdinievole , Maremma and the area close to Montecatini Terme. We lead groups in Chianti with wine and food tasting. We also think that two of the most interesting areas of Tuscany are the geothermal area between Grosseto and Livorno and the archaeological area in the Southern Tuscany where Etruscan developed their cities and where today we can visit the Etruscan ruins close to seaside and much more. Local expert guides will give your groups information, safety and reliability. Well tested trails in Tuscany, visiting naturalistic site, heritage, Middle Age villages and ruins.

Cycling and hiking in Tuscany with your group on the best and significant trails of Tuscany. Insert our tours during your holiday and enjoy hikes in Tuscany.  If you can’t find a solution right for you on this pages ask us for tailor made trails. HikingTuscany.com can design the best solution for you.

Don’t limit your visit to Tuscany to cities of art. Enter in the real Tuscany, in its countryside, woodland, marshes, seaside and rocky coasts. Breath the scent of Tuscany with our local guides hiking in Tuscany with us. Why choose a self-guided tour in Tuscany, when you can enjoy a safe a surely interesting trail with a local guide? Choose our solutions. Our team will propose you exiting trails in Tuscany. Not the common and tourists ones, but the trails most significant and interesting in order to let you visit the real landscape, the real environment and nature of Tuscany. You will find out wild flowers, animals, farm during cycling and hiking in Tuscany.

Some of the best hikes in Tuscany:

Hiking in Chianti

Hiking in geothermic area

Etruscan graves and the rocky seaside

Birds in Tuscany

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“...one of the best vacations ever...”

Peggy and I had a fantastic walking tour in Tuscany! We want to give everyone in the Girosole organization who helped contribute a big “molto bene” for making this one of the best vacations ever. It’s obvious that Girosole had done a lot of research on the route, towns, accommodation and ristorantes. Everything that Girosole provided was first class. But what stood out for us was the customer service. We highly recommend Girosole and hope we’ll have the opportunity for returning – perhaps to explore Cinque Terre next time. Thanks once again for a memorable vacation.

“...wonderful and memorable experience...”

A truly wonderful and memorable experience! Luca was not only very knowledgeable and good company; he was always prepared to go the extra mile and nothing was too much trouble for him. We felt thoroughly spoilt. Thank you so much for all your efforts on our behalf. It really was a pleasure dealing with Girosole. Just as an aside: perhaps you should suggest that clients allow for A LOT of extra baggage space for pecorini cheese, paneforte, chianti classico vino, shoes and handbags!!!!!

“...enjoyed our trip immensely...”

Our trip was wonderful! Luca was an excellent guide, very efficient, knowledgeable, and personable. I enjoyed practicing my rusty Italian with him, & he taught me several proverbs & expressions. When he saw I was very interested in Alpine wildflowers he helped me find & identify some along the trails. He was a delightful companion. The tour was very well designed, in terms of our hiking ability & fitness level. We started with a fairly easy hike & worked our way up to more challenging. At the end we felt like we’d had a good workout, but were not exhausted. The other couple in our group were very close to us in terms of experience & fitness. We’d recommend your tours to any active people who want to see Italy off the beaten path. We enjoyed our trip immensely & will remember it (& Luca) fondly. Thanks!

"...the perfect combination..."

We had a marvelous trip, and much of it was due to the planning that went into the Girosole itinerary – it was the perfect combination of walking, scenery, history, culture, time spent with the group, and time to explore on our own. I can’t imagine a better way to see the Amalfi coast. Our guide Ulisse was very friendly and helpful – he did a wonderful job of keeping us organized, giving us the history of the area, and providing advice on things to do when we were on our own. We would like to travel again with Girosole (maybe Tuscany next time) and will certainly recommend the walking tours to all of our friends.

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Via Francigena: The Ultimate Walking Tour in Tuscany

By: Author Dave Lee

Posted on Last updated: March 20, 2024

My return to Florence after 20 years allowed me to revisit one of Italy's most beautiful cities. However, it was only a prelude to the main event: a one-week tour of Tuscany along the Via Francigena.

The Via Francigena is an ancient pilgrimage route from Canterbury, England, through France, Switzerland, and Italy. The journey ends in Rome.

Tuscany is home to 400km of the Via Francigena, offering visitors the chance to experience the countryside as pilgrims have for over 1,000 years.

My week on the Via Francigena was organized by S Cape Travels in partnership with Tuscany Tourism and the Adventure Travel Trade Association as part of my attendance at the 2018 Adventure Travel World Summit in Montecatini Terme.

Our guides included the wonderful Ottavia of S Cape Travels Italy and knowledgeable Roberta Ferraris, author of the official Via Francigena guidebook . As you'll see, the itinerary they created for us included time spent on the Via Francigena in northern, central, and southern Tuscany. We relied on van transfers to bridge the gaps.

Table of Contents

Day 1 – Arriving in Montecatini Terme

Day 2 – lunigiana to pontremoli, day 3 – filetto, pietrasanta, and lucca, day 4 – lucca to gambassi terme, day 5 – pieve di cellole, san gimignano, and siena, day 6 – walk san quirico to bagno vignoni, final thoughts on the via francigena.

Our tour began in Montecatini Terme, an 18th-century spa town centrally located in Tuscany, a little over an hour's train ride west of Florence.

Arrival day would be the easiest of the trip, as we only walked from Hotel Tuscany Inn by the train station to the 19th-century funicular for a ride up the hill to Montecatini Alto.

The original town was located on a hilltop, which made sense in medieval times, as it was easier to defend. At Ristorante La Torre, we had the first of many delicious meals highlighting regional Tuscan cuisine.

Courses included bruschetta (tomatoes, basil, and olive oil on bread), vegetable soup, Tuscan peasant food (made by mixing leftover bread with tomatoes into a mushy consistency), and various kinds of cheese and ice cream. There was plenty of red and white wine, as was the norm for us at the following lunches and dinners.

Tip: A room with a view doesn't have to cost a lot. Check Booking.com for last-minute deals. I recommend getting a hotel with a view north toward the old town. I did this for a night after the conference and was so glad I did. 

The following day, we were up early for breakfast and a van transfer to Cavezzana d'Antena, in northern Tuscany, near the Emilia-Romagna border. We were dropped off just shy of 11 a.m. local time. We followed the well-marked Via Francigena route through olive farms, the dirt trail hugging the hillside.

Our guides informed us that northern Tuscany is less visited than the south, and I could understand why. We were immersed in the forest much of the day, not walking amongst the rolling vineyards so commonly associated with this region of Italy.

However, the trail and scenery were at their most varied on this day, something we'd only come to appreciate by the end of the tour.

One moment, I'm taking a photo of Roberta in what looks like a lush green forest, and no more than ten minutes later, we're walking through multi-colored fall foliage , chestnuts crunching below our feet.

It was also our most physically active day. There were a handful of short but steep inclines, and I was huffing and puffing up all of them. Using my Fitbit Versa, I tracked our daily hikes and the total distance traveled.

On our second day, we walked 9.58 miles (15.4 km) over five hours and twenty-two minutes (including an hour break for lunch) on the trail. This amounted to 21,000 steps, about three to four times my average daily step count at home.

We were all grateful when we reached the spot for our picnic lunch overlooking the valley. Ottavia and Roberta got to work slicing bread and unpacking all the food we'd brought, including plenty of cheese, prosciutto, olives, grapes, and tomatoes. After an hour of chowing down and resting our feet in the sun, we packed up for the final downhill stretch to the medieval town of Pontremoli.

Pontremoli means “trembling bridge” in Italian, a name it got from a bridge that once crossed the Magra River, which runs through town. The most dramatic entrance into town is the Porto Parma, which we walked through on our way to the 1,000-year-old Piagnaro Castle.

Statue Stele Museum

The castle houses the Statue Stele Museum , which has become a repository for ancient stone statues found in the region, some dating back to 4,000 BC. Following a brief museum tour, we walked further into town to the main square before being scooped up by our van for the 15-minute ride to the hotel.

Dinner at the hotel highlighted regional favorites, including Lunigiana testaroli with pesto, beef tagliata with rocket and parmesan, and apple cake with hot cream for dessert. Exhausted from a long day two of our walking tour in Tuscany, I fell asleep quickly after dinner.

On our third day, we woke up to grey skies and light rain. Following breakfast at the hotel, we took the van to visit Pieve di Sorano, a 10th-century Romanesque church in Filattiera.

Pilgrims would stop in churches like this as they traveled south on the Via Francigena to Rome. This particular church has been robbed in the past, so the interior can only be viewed by appointment.

Due to the rain, our guides offered us the choice of spending the rest of the morning doing an olive oil tour and tasting. We didn't have time for the second day or to walk a short section of the Via Francigena as planned. I chose the olive oil experience, as it's a product I use almost daily to cook with at home.

Olive Oil Tour and Tasting

Perched above Pontremoli, along the section of the Via Francigena we'd hiked the day before, is Francesca Ferrari's olive farm , which she runs with her husband Paolo (and adopted dog Homer).

After they purchased the old stone house and property in 2005, it took the couple several years to clean it up as it had been left in terrible condition. In 2009, they began using the basement and former wine cellar as an educational and training space, and in 2011, they started renting four guest rooms to visitors.

At just nine hectares, it's a small family-run business focusing on quality over quantity. They do everything on-site, from growing and pressing the olives to packaging the extra virgin olive oil. We were visiting a few weeks before the annual harvest in early November.

While outside, Francesca gave us their company's history, Lucchetti Ferrari, and then led us into the basement, where she explained the olive oil-making process.

For the tasting, we first sipped the extra virgin olive oil straight from a clear shot glass. Then she presented us with homemade honey chestnut bread drizzled with oil and a small container of their oil to take home.

Lunch in Filetto

Once the tour was over, we reunited with the rest of our group for lunch at Alla Piazza di Sopra , a charming spot in the town of Filetto just south of Filatteria.

As you can tell from the photo above, lunch consisted of many little things, including a variety of local cheeses (always my favorite), pastries, and colorful grilled vegetables. For dessert, we were served warm almond-flavored cake.

Pietrasanta

Following a relaxing lunch, we left Filetto by van for the one-hour drive south to Pietrasanta, an ancient Roman town located a few miles inland from the coast at the base of the Apuan Alps.

During the drive, we saw evidence of the marble quarries carved into the mountains. The region was an essential source of marble for artisans during the Renaissance.

At the center of Pietrasanta is the Piazza Duomo, a historic plaza lined with churches and museums. The plaza is regularly used to display art, such as the collection of sculptures depicting heads in various forms and materials pictured above.

Marble Studio Tour

In keeping with what the region is known for, we had the opportunity to tour a working marble studio.

Cervietti Franco S.N.C. has been a family-run business for generations. Walking through the warehouse with the owner, training his son to take over the family business, was a novel experience. The studio uses local marble and traditional and modern methods to serve clients worldwide.

The sizes of the sculptures they produce range from small to monumental. Many were religious figures, though I spotted the face of Michael Jackson, too. Raw marble is also exported worldwide, and we were told a handful of powerful families control the mines.

Dinner in Lucca

We left the marble studio for the walled city of Lucca, a UNESCO World Heritage site 40 minutes away. After checking into our hotel just outside the city walls, we walked into the old town for dinner at Ristorante Mecenate .

On the menu tonight are a delicious caramelized onion tart, prosciutto, a red pepper pudding you smear on bread, testaroli pasta with pesto, breaded and fried beef topped with tomato sauce and capers, and custard for dessert.

Guided tour of Lucca

Our morning began with a guided tour of Lucca, a city that became a Roman colony in 180 BC. The three miles (five kilometers) of walls were built for defensive purposes in the 16th century. When the need to defend the city passed, the tops of the walls were repurposed as streets and pedestrian walkways.

Highlights of our walk included:

• Lucca Cathedral
• Chiesa di San Michele in Foro (church) and Davino, the mummified remains of an 11th-century pilgrim from Armenia enshrined at the altar
• Basilica di San Frediano Lucca (there's a beautiful gold mosaic on the facade)
• Piazza dell'Anfiteatro, a plaza at the center of an old Roman coliseum that once sat 10,000 people
• 12th and 13th-century towers

Lucca is a city I could easily spend a few days exploring.

Tip: Lucca is an easy day trip from Florence. Check out Get Your Guide for tours of Lucca . 

Lunch on an Organic Farm

It was an hour's drive southeast from Lucca to reach our lunch spot, The Doctor's Cheese  in Coiano. Since 2009, Guido and his wife Stefania have produced high-quality organic cheeses using cow, goat, and sheep milk.

They welcomed us with big smiles and an even bigger spread of their cheeses, including an earthy truffle cheese (my favorite) and ricotta with honey (I had more than one serving of that, too).

Since men and women cannot survive on cheese alone, they also provide bruschetta, raw wild boar marinated in olive oil, boar sausage, and bruschetta.

The setting for lunch was idyllic–a few picnic tables in front of the farmhouse with views of the surrounding hills. It was one of the many “pinch me; I can't believe this is real” moments from our walking tour in Tuscany.

Read more about my lunch on an organic farm in Tuscany on Feastio.

Walk from Coiano to Gambassi Terme

After lunch, it was time for us to put in some miles on the Via Francigena. Roberta opened her map and briefly briefed us on our afternoon walk from Coiano to Gambassi Terme.

We set off on foot from the farm, walking uphill through olive trees until we reconnected with the trail. Soon, we walked briskly along ridges with panoramic views of the Tuscan countryside.

It was a reasonably easy and relatively flat stretch of the Via Francigena, ending with walks through several vineyards. But between the warmer-than-usual weather and sun exposure, I worked up quite a sweat. We covered 6.4 miles (10.3 km) over two and a half hours.

Pieve of Saint Maria

We hopped in the van for the 15-minute drive to Pieve of Santa Maria, another Romanesque church visited by pilgrims on the Via Francigena.

Adjacent to the church is Ostello Sigerico, a hostel where we met an Irish pilgrim walking the length of the Via Francigena from Canterbury to Rome. He estimated that he would need another two weeks to finish, making his full traverse of the trail a three-month affair.

We couldn't help but notice he was using the official guide for the Via Francigena, written by our guide, Roberta. We brought this detail to his attention, which delighted him, and he then asked for her autograph.

He also showed us his Pilgrim Passport , an informal ID that serves as both a souvenir and a way to identify one's pilgrim status on the Via Francigena.

The benefit of carrying the Pilgrim Passport is that it can help you gain access to churches and monasteries and benefit from discounts from some hotels, B&Bs, hostels, and restaurants.

Meeting this gentleman brought the whole experience to life in a new way. The Via Francigena wasn't just a trail used a thousand years ago. It's alive and well today, too.

Our accommodation for the night was Tenuta Sant'Ilario , a gorgeous family-run agriturismo hotel in an old stone farmhouse.

The hotel produces olive oil and wine, and there's a small restaurant on the property where we had a delicious three-course dinner (ricotta cheesecake, pork loin, and pannacotta).

We began walking straight from the hotel after breakfast on our fifth morning. It was nice not having to get in the van, and I much prefer walking in the morning when the sun isn't so high in the sky. The weather was beautiful, and the trail was pretty flat that day.

We mainly walked along dirt roads past vineyards, precisely the kind of imagery I had in mind when I decided to attend the Adventure Travel World Summit in Tuscany.

We even encountered some men picking grapes by hand in one vineyard (and they were okay with us taking photos of them, too). These scenes always remind me of the I Love Lucy episode, in which Lucy smashes grapes in a barrel with her feet.

We walked down cypress-lined roads, past old stone homes now rented out on Airbnb. I know this because one owner was in his yard and all too happy to come out and chat with us. We also passed hunters out with their dogs searching for wild boars, rabbits, and other game.

In total, we walked just shy of three hours, covering 7 miles (11km) at a 25-minute pace. As some in our group (me!) felt knackered, we hopped in the van for the final stretch to a thousand-year-old church.

Pieve di Santa Maria Assunta a Cellole

The Pieve di Santa Maria Assunta a Cellole is another church along the Via Francigena that pilgrims visited en route to Rome. It's now part of the Monastery of Bose , which was built around it.

When we peeked into the church around noon, monks were praying and chanting, so we couldn't enter. However, it's a peaceful setting to pursue religious studies and undoubtedly worth a brief visit.

Visit San Gimignano (UNESCO)

The church and monastery are on the outskirts of San Gimignano, a UNESCO World Heritage Site 35 miles (56km) southwest of Florence. The city was an essential pilgrimage stop and an easy day trip from Florence.

The ruling families who once oversaw San Gimignano built towers as signs of wealth and power. It's estimated there were once 72 such towers in the town, though only 14 remain standing today.

Before touring the town, we had a relaxing and well-deserved lunch at  Ristorante Osteria Delle Catene , featuring local wine, bread, cheese, soup, and incredibly delicious white beans.

For dessert, a cake smothered in lemon cream. And a cappuccino, because this is Italy.

It was also recommended we try the gelato in the main square. There are two popular options: Gelateria Dell'Olmo, which bills itself as the best gelato in the world above the door, and Gelateria Dondoli, owned by Sergio, a world-champion gelato maker.

The latter had a longer line, but our guide, Ottavia, recommended the former, so I went there. I can't recall exactly what I ordered, but it was definitely chocolate, and the other flavor was either vanilla or mascarpone. It was delicious.

A sign of high-quality gelato is that it melts slowly, even in the sun or warm weather. This is good news for those of us who are trying to take photos with our phones before we make a mess!

Powered by coffee and gelato, it was time to climb the 177-foot (54m) Torre Grossa . The top offers spectacular views of the town and countryside. I highly recommend it!

Tip: If you're based in Florence, you can visit San Gimignano directly or as part of an extended day tour with additional stops in Tuscany. Check out Get Your Guide for options. 

Dinner in Siena (UNESCO)

We left San Gimignano around 5 p.m. by van for a one-hour drive to Siena, another UNESCO World Heritage city.

With less than two hours to spare between checking into our rooms at La Villa di STR and dinner, I showered and went for a walk on my own to see the impressive Siena Cathedral (Duomo di Siena) and iconic Piazza del Campo (above).

The plaza hosts the Palio di Siena , an annual horse race where dirt is laid down, and jockeys ride bareback around the track for three laps. The competition lasts about 90 seconds. Such events date back to medieval times.

As much as I wanted to see Siena by day and spend more time there, I have to admit it's incredible by night, and I'm glad to have had at least a small taste of it. Along with Lucca, I'd love to go back one day.

Speaking of taste, we dined al fresco at Il Pomodorino , with views of the cathedral in the distance. An enormous amount of antipasto (mixed meats, cheeses, olives) and pizza was served. My mouth waters just looking at the photo of the white pizza above.

San Quirico d’Orcia

Our final morning of the trip began with breakfast at the hotel and a one-hour drive south to the quaint little town of San Quirico d'Orcia. We took our time walking down the main street and ducking into the pretty Community Gardens (Horti Leonini). On our way out, we ran straight into a parade from the opposite direction.

Walk through Val d'Orcia from San Quirico to Bagno Vignoni (UNESCO)

Once the parade had passed, Roberta led us out of town to rejoin the Via Francigena. On our sixth and final day, we walked 6 miles (10km) through the Val d'Orcia, a UNESCO World Heritage Site.

Per UNESCO :

The landscape of Val d’Orcia is part of the agricultural hinterland of Siena, redrawn and developed when it was integrated in the territory of the city-state in the 14th and 15th centuries to reflect an idealized model of good governance and to create an aesthetically pleasing picture. The landscape’s distinctive aesthetics, flat chalk plains out of which rise almost conical hills with fortified settlements on top, inspired many artists.

Once again, we were walking on relatively flat dirt roads.

Related: Walking the Camino de Santiago

We stopped in a picturesque hamlet for a picnic lunch on the steps of the small San Biagio church. A friendly cat quickly endeared himself to everyone as we gobbled down our last helpings of bread, cheese, prosciutto, and fruit from the tour.

Bagno Vignoni

Our walk concluded in Bagno Vignoni, known for its thermal pool in the central plaza. There wasn't much to see beyond the pool, which would be a sweet spot to grab lunch, so we mainly hung out in a gelato shop. I broke with tradition, ordering strawberries instead of chocolate.

Wine Tasting at Casato Prime Donne

Our last stop was a wine tour and tasting at Casato Prime Donne in Montalcino, a 30-minute drive north of Bagno Vignoni (about 50 minutes south of Siena).

Casato Prime Donne was Italy's first all-female winery, and artwork by women featured inspiring quotes on the grounds. The land we were on has been in Donatella Cinelli Colombini's family for 500 years.

The tour began with our first tasting in the gift shop. After that, we left the main building to taste our second wine next to the Tinaia “del Vento” or Windy Fermentation Room. Eight stainless steel vats under a shed-like roof face the vineyards from which the grapes are grown.

According to their website, this area was designed to “experiment with indigenous yeasts out in the open.” Our third tasting was in the wine cellar, where we saw something I'd never seen before in a fermentation room — concrete vats. I learned concrete was used long before stainless steel to make wine.

Roberto Turchi, a painter, is projected onto the vats and a screen as classical music plays. The history, music, and visuals made our visit to Casato Prime Donne one I won't soon forget.

Our tour ended with a two-and-a-half-hour drive back to Montecatini Terme, where it all began.

As this article grew by the day, I debated breaking it into several smaller stories. I stuck with one to demonstrate how much there is to see, do, and eat if you go for a walking tour in Tuscany along the Via Francigena. My week was rich in landscapes, culture, history, food, wine, and new friends.

One thing I haven't mentioned yet is the trail markings. They were everywhere on the sections we walked. Tuscany has taken the lead in improving and promoting the Via Francigena in Italy, and it shows.

I have little experience hiking without a guide, especially on multi-day trips. However, based on what I saw, I would feel comfortable stretching my comfort zone and hiking solo using the official guidebook . More experienced hikers and trekkers would likely find it easy.

Another option is the  self-guided trips  offered by S-Cape Travel. The tour price includes logistical support and hotels, as well as a mobile app that provides your GPS location on the trail.

Dave is the Founder and Editor in Chief of Go Backpacking and Feastio . He's been to 66 countries and lived in Colombia and Peru. Read the full story of how he became a travel blogger.

Planning a trip? Go Backpacking recommends:

• G Adventures for small group tours.
• Hostelworld for booking hostels.

The 11 best things to do in Tuscany

O ne of Tuscany's main draws is that it has something for every type of traveller and, in fact, you can create a fully rounded itinerary even if you only have a few days.

Here is our guide to the best things to do in the region, from biking down classic country roads to truffle hunting in the woods, to scoring an antique heirloom, or blending your wine like a Renaissance man, plus insider tips on where to find the best tomato, or fresco.

For further inspiration, see our  guide to Tuscany  and its best hotels , restaurants , beaches and drives .

Enjoy a glass of wine with a side of Modernist architecture

Modern architecture is not something you see often in Italy, particularly in Tuscany, which makes Antinori nel Chianti Classico, a new showcase for Antinori’s vintages, even more groundbreaking. A visionary soaring complex of steel and light, it calls to mind Richard Serra’s sculptures. Situated outside the town of Bargiano, about 20 minutes' drive from Florence, the showstopper was designed by architectural firm, Archea. Inside the structure, which took seven years to design and construct, the layout is a mixture of cantina, bar, restaurant and museum, all dedicated to the famous Antinori wines. 

Insider tip: To taste a number of vintages rather than choosing a bottle, sample a flight of the label’s range at the property’s tasting room.

Contact:   antinori.it

Price:  ££

Get back to the land with a visit to an organic farm

Podere Il Casale, an organic farm close to Montepulciano and Pienza, exemplifies Tuscany’s zero-mile approach to food (getting ingredients from home, or as close to home, as possible). The property, owned by a Swiss family who fell in love with Italy, has a hippie bohemian feel as peacocks and sheep wander about and volunteers help out, sleeping in campers at night. Come to see how they make cheese and then sit down to sample their sustainable and seasonal menu. 

Insider tip:  Be sure to pick up a jar of their homemade honey too.

Contact:   podereilcasale.com

Head to the woods to sniff out a truffle

This prized ingredient is one of Tuscany’s and Italy’s most famous products, a kind of foodie couture. Sniffed out by dogs or pigs, the best of them sell for exorbitant prices internationally but here you can get them for a fraction of the price. Even more fun is to set up a truffle hunting tour that finishes with you sampling your own truffle with a plate of local pasta. The hunters and their dogs who accompany you seem right out of central casting. Book your hunt with a good outfitter such as  Select Italy  or Truffle Hunter . 

Insider tip: You can find black truffles here much of the year but for the prized white variety book your trip for October or November.

Join the party at one of the region's festivals

All over Italy the concept of the local festa (festival) thrives and Tuscany is no exception. Most visitors to the region will be familiar with Siena’s Palio , the twice-a-summer bareback horse race that pits contrada (neighborhood) against contrada , in a most medieval way. But it’s only one of the spectacles on offer. In Montepulciano at the Botte di Bravio, two men roll 50kg barrels up the city’s twisted streets in a way that makes Crossfit look wimpy. Meanwhile in Pienza at the Fiera del Cacio, teams of children and adults put a new spin on bowling, spinning pecorino cheese in circles in the town’s main square.

Insider tip: Join a neighborhood dinner after the competition, there are usually a few tickets on hand for non residents.

Learn how wine is made

Going to see how wine is made and the estates that turn out the best vintages has to be one of Tuscany’s main pleasures. The properties range from more professional tours (there is often a restaurant on site too) to small family producers where a call in advance to see if they are open is a must (your hotel should be able to set up a tour at most estates). Among the vineyards to consider: Avignonesi  is one of Montepulciano’s most famous producers for its Vino Nobile wine, which can be sampled at the property’s excellent restaurant. At Montalcino’s Casanova di Neri , a Brunello maker that has scored consistently in the high 90s in Wine Spectator, the tasting room can popped into without an appointment. 

Insider tip: Make time for smaller family operations too. Ask a local for their favorite low-key producer and where you can try a hand at blending.

Visit the thermal baths before enjoying a cocktail

Bagno Vignoni has long been on travelers’ radars for good reason. In the Middle Ages, it was a stop along the Via Francigena, the route that took pilgrims from Rome to France, and in this little town they found natural thermal springs to ease their muscles. Today, after exploring the thermal waters – either at the free springs just out of town or at a hotel like Il Albergo Posta Marcucci – visitors can head to the speakeasy Il Barriano a watering hole with elixirs so balanced and unusual even the monks would have been impressed. At the bar’s helm is Bledi Ndoci, an Albanese mixologist who came to Italy as a child and moved to the Val d’Orcia recently —try the Mais Amor with Tequila, Mezcal, Elicriso, corn, lime, and ginger salt. 

Insider tip: Heading into the Christmas holidays Bagno Vignoni is particularly delightful with its lit-up tree on the water and the mist coming off the central square in a ridiculously romantic way.

Contact:  facebook.com/ilbarrinobagnovignoni/

Take to the hills on a cycling tour

Even though Tuscany is most highly rated for its eating and drinking, sporty types will find lots to entertain and challenge thanks to the notoriously hilly landscape. Cycling is a favorite diversion here with outfitters such as  Duvine  and Backroads  specialising in tours through the region (one also can easily rent a bike for the day too and the proliferation of ebikes has made those epic hills a bit more manageable). Hikers will find paradise here too; there are hundreds of unpaved roads here called white roads that lead between towns and beautiful abbeys. Meanwhile if a Vespa is more your speed rent one through a company such as  Tuscany by Vespa .

Insider tip: Before your trip pick up a copy of Walking and Eating in Tuscany and Umbria – the authors suggest excellent walks that end with a great meal (try Montalcino to the Abbey of San’t Antimo).

Shop for sustainable products

One of the growing trends all over the country, from food producers to clothing designers, is to keep products as sustainable as possible, and made with quality ingredients, or textiles. The thinking is that with this kind of emphasis Italian labels will continue to be one of the greatest offering on the global market. Of course, this philosophy has been around for centuries. In Anghiari, for example, the showstopping linens and table wear at Busatti  have been made on looms here since 1842. At Tenuta di Spannocchia , a farm and castle that’s been around since 1225, extra virgin olive oil and multi-floral honey are only some of the organic and biodynamic products they make and sell on site. 

Insider tip: If you stay at a property like Tenuta di Spannocchia you can also learn about other projects like the raising of Tuscan farm animals, which were on the verge of going extinct. 

Explore the atmospheric markets

While many of the weekly markets have started selling as many cheap clothes as heirloom tomatoes, there are still some atmospheric and authentic options. One of the best has to be Greve in Chianti’s Il Pagliaio, held every fourth Sunday of the month, March through December. Everything on sale is organic and you can find seasonal gems such as Porcini mushrooms or melt in your mouth figs.

Other exceptional markets include Livorno’s Il Mercato Centrale, where a vast complex of stalls is housed in an impressive 19th-century building – not surprising considering the city’s location on the coast, the seafood choices are excellent. And Carrara, known for its beautiful white marble, also has a famous market, the Mercato delle Erbe, held every Saturday morning, and highly rated for its organic focus.

Insider tip : If antiques are more your passion, make tracks to Arrezzo, which takes place the first weekend of the month. Candlesticks and jewellery are only a few of the finds to put in your suitcase. 

Marvel at a park full of sculptures

Capalbio, a lovely town close to the sea, has long been the preferred second home choice for noble Romans and the society set. Its beautiful beaches and easy proximity to the Eternal City, make it a popular choice for short breaks, but there’s a less well-known attraction that’s more than worth a stop. The town’s ‘Tarot Garden’ – Il Giardino dei Tarocchi – is home to a series of sculptures by Niki de Saint Phalle (she envisioned her creation in a dream while she was shut up in an asylum). These 12-15 meter high sculptures scattered through a 14-acre garden atop Etruscan ruins are made from mosaics and are one of the most famous works by the artist. The surreal kaleidoscope renditions represent each card of the tarot deck – a sphinx, for example, comes with mirrored blue hair and a red crown, one breast covered by a flower and the other by a purple heart. 

Insider Tip: Sample the Italians take on glamping nearby with a stay at the lodges of Terra di Sacra in a WWF refuge and close to chic beach clubs like La Dogana. 

Contact:   ilgiardinodeitarocchi.it

Visit a child-friendly vineyard

Illy is a world-renowned name in the coffee universe, but less well known is the family’s foray into the wine world at the spectacular Podere ai Ripi vineyard outside of Brunello-famous Montalcino. Biodynamic and organic, the wine has quickly risen to award-winning status thanks to the loving attention of owner Francesco Illy and his main oenologist, Sebastian Nasello. The unusual circular cantina known as the “golden cellar” is state-of-the-art, and we love the wines’ names like Amore e Magia (love and magic), Amore e Follia (love and folly,) and Lupi e Sirene (wolves and mermaids). One of the best aspects of the property is how child-friendly it is: instead of waiting impatiently for parents to finish their seemingly endless tastings, children can gather eggs, pet the donkeys and other animals like the beautiful Chianina cattle, and dress up like a farmer while learning about the property’s eco-sustainable garden. 

Insider tip: Before or after your vineyard visit head to the 12th century abbey of Sant’ Antimo, one of the most beautiful structures in all of Tuscany. 

Contact: podereleripi.com

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11 Best Hotels in Tuscany, From the Coast to the Outskirts of Florence

By Alex Erdekian

While Tuscany is hands-down one of the best places in Italy to visit, there's no getting around it—it's difficult to plan a trip there. The myriad of tiny towns you've never heard of, vineyards, hills, and networks of highways to cross en route to your destination are the region's entire charm, but also are what makes it so complicated to navigate. However, a great hotel (and accommodating concierge) can help smooth out the process—which is why we've rounded up Condé Nast Traveler's highest regarded Tuscany hotels. Read on for 11 of the best hotels in Tuscany.

Every hotel on this list has been selected independently by our editors and reviewed by a Condé Nast Traveler journalist who knows the destination and has visited that property. When choosing hotels, our editors consider properties across price points that offer an authentic and insider experience of a destination, keeping design, location, service, and sustainability credentials top of mind.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

La Roqqa Arrow

The location: Porto Ercole, an area with built in exclusivity due to a hard to reach location on a quiet bay

Top amenities: Balconies or terraces in every room; everything from hiking and biking tours to horse riding or wine tasting tours can be arranged by the guest services team

It’s been eons since a new hotel graced Porto Ercole, a chic but discreet village on the Monte Argentario peninsula that’s home to Caravaggio’s tomb. The newcomer creating ripples on this part of the rock-strewn Maremma coastline is petite La Roqqa, a cliffside retreat whose distinctive coral-orange façade and secluded views of the Tyrrhenian Sea provide a forward-looking alternative to Hotel Il Pellicano, the area’s sine qua non grande dame since 1965. In the 55 rooms and suites, floor-to-ceiling windows let sunshine flood onto walls of sage green or Terra di Siena orange, which pop against crisp white bed linen. Designers Palomba Serafini, Milanese masters of uncluttered contemporary chic, have mixed midcentury pieces and Gaetano Pesce’s iconic Up chairs with ultramodern features, including an eye-catching white central staircase spiraling from the entrance. On the alfresco rooftop, Ferragamo-clad locals sip Negronis gilded by sunset rays in view of the 16th-century Forte Stella and harbor yachts below. Aperitivo hour turns into dinner at the outdoor Scirocco restaurant, where chef Francesco Ferretti knocks up fresh sea bass and other local seafood capped with Venetian grappa. Days spent lounging at the hotel’s smart Isolotto Beach Club are broken up by lunches of avocado and tuna salads paired with a local white. Or you can ask friendly staff to book you a Vespa tour along the rugged coast. It’s la dolce vita reimagined for the next generation. —Erin Florio

Hotel Il Pelicano Arrow

Porto Ercole

The location: Porto Ercole, a coastal town in Southern Tuscany situated around a yacht-filled harbor, halfway between Florence and Rome Top amenities: The beach club—one of Italy's best oceanfront properties, and a 2023 Michelin-starred restaurant

Il Pelicano is one of Italy's most legendary and best-known hotels, one which has been open since 1979 and where Sophia Loren and other Hollywood royalty have stayed. The bedrooms are crisp and bright: some have ocean views, some have balconies and terraces, and some have floors made of Carrera marble. The more casual restaurant, Pelligrill, is considered a classic with the yacht crowd and overlooks the pool and ocean, perfect for sunset; while the 2023 Michelin-starred Restaurant Il Pellicano earned accolades for its creative uses of ingredients from land and sea including pigeon, lobster, and shrimp.

Casa Iris Arrow

The location: Orbetello, a small, walled coastal town on a lagoon and a peninsula, Grosseto, once the site of an ancient Etruscan settlement; located midway between Florence and Rome

Top amenities: Breakfast served, highly personal service from the two owners

This luxurious, all-done-up bed and breakfast, set in a peach colored palazzo on the town's main drag, is highly personal, with just three bedrooms inside and the owners filling the roles of concierges. Before they purchased it, the 15th century property was full of historic frescoes—the owners proceeded to hire a restorer who had worked on the Sistine Chapel to make it their own. A cozy breakfast is served to guests in the communal kitchen, featuring fresh apricot jam; and the rooms are works of art, with walls whose historic layers of paint have been scraped into designs.

Rosewood Castiglion del Bosco Arrow

The location: Montalcino, a hilltop town famed for its production of Brunello di Montalcino wine, made from the town's sangiovese grosso grapes—it's an hour and a half by car from Florence and 45 minutes by car from Siena

Top amenities: On-site Brunello di Montalcino winery, 18-hole golf course, cooking classes, spa, infinity pool, truffle-hunting outings

We've already listed the terrific amenities—which, yes, include truffle hunting—but if you need more information on Rosewood Castiglion del Bosco, we'll go on. This Tuscan estate is on 5,000 acres and has 42 suites and 11 villas. Travel reporter and Condé Nast Traveler contributor Laura Itzkowitz —who lived in Rome previously and writes often about Italy—describes the bedrooms as “lavish” in her hotel review for the magazine:

“If money were no object,” she writes, “I would check into one of the sumptuous villas and never leave. Each one comes with a private heated pool, though some feature woodburning pizza ovens, a home theater, or tennis court.”

Shannon McMahon

Chris Schalkx

Caitlin Morton

Emily Pennington

Castello di Vicarello Arrow

Poggi del Sasso

The location: A true village in central Italy with a population of 88

Top amenities: Vegetable garden with ingredients used in food on-site, yoga, alfresco spa

This nine-suite retreat, formerly an actual family home, is set within a 12th century medieval castle. But in spite of the down-home, rustic setting—there are no TVs—this place is totally chic. Mario Testino shot a Vogue photo shoot here featuring Lara Stone. The food is an offering that sets Castello di Vicarello apart from the others in the Tuscany hotel landscape. Here's how contributor Sophie Goodwin describes it in her first-person Condé Nast Traveler hotel review: “Ingredients are fresh from the vegetable garden, eggs straight from the chicken coop, and cakes and bread baked every morning. Breakfast is slices of Pecorino with bread, eggs with sunny orange yolks, and strong Italian coffee. Wild boar is breaded and served with a dollop of olive-oily-aioli, the al-dente spaghetti comes with fresh tomato.”

We don't need any more convincing.

Renaissance Tuscany Il Ciocco Resort & Spa Arrow

The location: Outside the walled medieval city of Lucca, an all-time classic day trip from Florence

Top amenities: Spa, pool, bar, 24-hour service

The Renaissance Tuscany Il Ciocco Resort & Spa, a 180-room luxury resort hotel by Marriott International, is surrounded by 1,500 acres of green hills and land—and by all of the special perks, amenities, and experiences you would expect from the brand. These include marble bathrooms in the rooms, cooking classes from the restaurant, and destination weddings packages. The ideal location in the heart of Tuscany means exploring the region's vineyards, tasting wine, and biking, hiking, and horseback riding are all activities on demand—not to mention the ability to stroll through the historic towns of Lucca and Barga.

Fontelunga Hotel & Villas Arrow

The location: The city of Arezzo, in eastern Tuscany, is well-known among history buffs and wine enthusiasts alike, and is home to a famed 15th century fresco of Mary Magdalene, as well as ample Chianti wine vineyards

Top amenities: Complimentary breakfast and bicycles, pool bar, on-site dinner parties, private cooking lessons at an extra cost

Italy writer Bridget Arsenault kicks off her hotel review of Villa Fontelunga in the dreamiest way possible:

“Set amid 200 olive trees,” she writes, “Villa Fontelunga's marmalade-colored building appears against the blue sky as you enter the driveway. Set within the beautiful hilltop town of Cortona, the hotel offers spectacular views across the Val di Chiana in the heart of Tuscany. An intimate, fairly remote Tuscan getaway, this hotel takes some research to track down. Once there, you'll find everyone from honeymooners to Italian adventure-seekers inspired by Under The Tuscan Sun to retired couples enjoying la dolce vita.” If that isn't inspiring enough, the details she reports—including the two tiny dogs who run around the property, the Tuesday and Thursday chef-hosted dinner parties, and the honesty bar by the pool—really seal the deal.

Relais Sant'Elena Arrow

The location: Bibbona, situated between beach and forest, and home to a centuries-old fortress and medieval piazzas Top amenities: Complimentary breakfast with an Instagrammable spread, guided farm tour with olive oil tasting, cooking class, holistic spa

This dreamy farmhouse-style 16-room boutique hotel emulates the Tuscan experience to a tee. Guests enter a secluded tangle of ivy, rose gardens, stone walls, and wood beams, the stuff of Italian storybooks. The rooms and the dining program alike are top-tier. Bedrooms are full of antiques and rain showers, while the food offered includes fresh ingredients from the on-site garden and olive oil made on-property. The food was the favorite part for reviewer, Bridget Arsenault again, who also highly recommends the bookable cooking class:

“There's daily lunch (poolside or in the whimsical garden) and you can order drinks throughout the day,” she writes. “Dinner is an otherworldly affair. You can also book an on-site cooking class and learn to make Tuscan classics like ribollita and pappa al pomodoro, fresh pastas with ragu, and tiramisu.”

She also reports a romantic vibe, and says that you'll find plenty of honeymooners and couples here.

Cala del Porto Arrow

The location: Harbor-side, in a small town on Tuscany's Southern coast

Top amenities: Sister property Cala Beach located directly on the beach, hands-on winemaking opportunity, bookable experiences including cycling tours in the Maremma and day trips to the archipelago's island

It's hard to go wrong when you're staying on a serene archipelago surrounded by turquoise harbors, smack between land and sea—the glittering ocean and Tuscan wine country. At Cala del Porto, guests get the best of both worlds. But the resort itself takes the joys even further with five-star service, in-room balconies, four restaurants, and planned experiences and excursions that are made accessible, including private yacht tours, golfing and wellness packages, and biking and wine tasting tours.

Hotel Adler Thermae Arrow

Bagno Vignoni

The location: Bagno Vignoni, a hamlet in the province of Siena well-known for its dramatic hot springs, overlooking Val d'Orcia, a UNESCO World Heritage Site since 2004

Top amenities: Thermal swimming pools, sauna, steam bath, holistic spa

One of the most unique places to stay on this list, Hotel Adler Thermae makes use of its location on Tuscany's hot springs in the most delicious way possible—by providing a compound of thermal swimming pools, baths, and spas full of travertine grottoes, stalactites, and stalagmites, for guests to luxuriate in. Staying somewhere like this is one of those wish list travel experiences most people only dream about. The resort has plenty of other things going for it too, though: a glass-roofed restaurant, stellar wine list, and in-room terraces, to name a few.

Castel Monastero Arrow

Castelnuovo Berardenga

The location: Castelnuovo Berardenga, a village that's a day trip from Florence, full of castles and Romanesque churches Top amenities: Interlocking swimming pools

Castel Monastero, a castle of a hotel 15 miles from Siena with 75 guest rooms, is well-situated for the quintessential Tuscany trip. The spacious accommodations here have “wood beams, comfortable leather sofas, terra-cotta floors, and views into the valley,” according Traveler 's review of the hotel. The interlocking swimming pools have those picture-perfect valley views, as well. Oh, and how could we forget? There's also a 13th century wine cellar on the property.

For more inspiration, see our first-hand researched rankings of Italy's best hotels, Airbnbs, and villas.

Editor picks:

• Our Ultimate Italy Where-to-Stay Guide
• Best Hotels in Florence
• Best Hotels in Rome
• Best Hotels in Venice
• Best Airbnbs in Italy
• Best Airbnbs in Rome
• Best Airbnbs in Venice
• Best Villas in Italy
• Best Villas in Tuscany
• Best Villas in Lake Como

2023 Readers' Choice Awards picks:

• Best Hotels in Italy, According to Readers
• Best Hotels in Florence, According to Readers
• Best Hotels in Rome, According to Readers
• Best Hotels in Venice, According to Readers