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Italy self guided bike tours are available any date in our unique ‘always private’ format! We can offer any of the trips in a private guided version as well.  All of our self guided bike tours shown below include superior lodging, local support, and exceptional customer service ! Custom guided groups welcome! Have questions, or can’t decide which is best for you?  Contact us ! Our friendly team is ready to help!

Italy – Tuscany Escape Short Bike Tour

Italy – Puglia Short Escape Bike Tour

Italy – Eastern Sicily Baroque Discovery Bike Tour

Italy – Tuscany Etruscan Treasures Bike Tour

Italy – Sardinia Discovery Bike Tour

Italy – Best of Puglia Cycling Tour

Italy – Piedmont Wine Country E-bike Tour

Tailwind on every ride? – See e-bike trips

Book your fall training now – see Ride Camps

European Classic booking fast – see the trips

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Tuscany Bike Tour

Tuscany Self-Guided Bike Tour

Val d'Orcia — Explore the beating heart of the Tuscan countryside

Tour Duration

Self-Guided

Activity level.

Hotel Level

Trek Domane SL 7 Gen 3 Trek Electric-Assist Verve+

Starting from

$ 2,199.00 per person

Have a question?

See the Tuscany you've always imagined on this self-guided bike tour, with its incomparable riding, breathtaking beauty, and rich culture.

Every day is your perfect day on our Tuscany self-guided tour as you weave your way through the heart of this famed region. You’ll get to discover at your own pace all the wonders of this captivating landscape. As you pedal over golden, rolling hills, explore the serene beauty of cypress-framed paths, ancient farms, and hilltop villages that sit behind towering medieval walls. Tuscany's culinary legacy, from its fresh, simple cuisine to world-class wines, complements the experience at every turn. We have designed a perfectly curated itinerary so that you can create your very own ideal experience and spend your time savoring each and every moment. Learn more about Self-Guided trips and if they're right for you »

Ride along quiet roads lined with cypress trees in the beautiful Tuscan landscape

Stay in a historic building which has been transformed into an elegant and charming hotel

Explore the unique cultural landscape of Val d'Orcia designated a UNESCO World Heritage Site

Pamper yourself with the world-famous Brunello di Montalcino wine and "vino nobile" di Montepulciano

Indulge in fresh Tuscan pasta dishes and discover local pecorino cheese

Vineyards sprawling across hillside in Tuscany

What Guests are Saying

All was great. Traveling without the hassle of bikes was worth every penny. Having the routes pre-loaded made for ease when unsure where to go ride safely.

Liz, Trek Travel Guest

The rides were phenomenal. Great conditions, great views, great challenges, all very rewarding. Even with selecting the long option ride, I still found the balance of down time to be great. There's enough flexibility within to make the trip YOUR OWN trip. Excellent job.

Carolyn., Trek Travel Guest

An amazing trip. We were married in Florence the day before our Trek trip started. It was the best way to spend our honeymoon. We were able to spend time together cycling which is an activity that brought us together and that we are both very passionate about!

Brian, Trek Travel Guest

Love these bikes and routes, and Jonathan, our bike expert in San Quirico!!! Having the bike garage with light charging stations was a huge help. My daughter in law now wants to buy a new Trek road bike!

Jeannie, Trek Travel Guest

Great location. Charming village with more restaurant options than I expected. Loved being in just one place. Plenty of options on rides. Lorenzo was a gracious manager and available to address any issues. The accommodations were perfect. Very comfortable and quiet. The breakfasts from the hotel’s top class restaurant were great.

Brett, Trek Travel Guest

San Quirico to San Giovanni d'Asso Loop

The "Crete Senesi" offers one of the most photographed rural landscapes in the world: cultivated fields crossed by rows of cypresses and unparalleled views.

Dates & Pricing

Book early for the best price

Join Waitlist

Limited Availability

April 22-26, 2024 limited availability.

Hotels you`ll stay at on this date:

• Hotel Villa Liberty

Available bikes:

• Trek Electric-Assist Verve+ 3

$ 2199.00 per person

Double Occupancy

Single Occupancy from: + 999.00

May 20-24, 2024

• Trek Domane SL 7

June 3-7, 2024

June 10-14, 2024, june 17-21, 2024, june 24-28, 2024, july 1-5, 2024, september 2-6, 2024 limited availability, september 9-13, 2024 limited availability, september 16-20, 2024 limited availability, september 23-27, 2024, october 7-11, 2024, october 14-18, 2024, april 14-18, 2025, april 21-25, 2025, april 28-may 2, 2025, may 5-9, 2025, may 12-16, 2025, may 19-23, 2025, may 26-30, 2025, june 2-6, 2025, june 9-13, 2025, june 16-20, 2025, june 23-27, 2025, september 1-5, 2025, september 8-12, 2025, september 15-19, 2025, september 22-26, 2025, september 29-october 3, 2025, october 6-10, 2025, october 13-17, 2025.

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Arrival / Departure

Where to Arrive

Amerigo Vespucci (Florence) Airport (FLR)

Pick-up location :

Villa Liberty Boutique Hotel, San Quirico d'Orcia

Pick-up time :

Where to Depart

Drop-off location :

Drop-off time :

Additional Arrival Information

We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Florence’s Amerigo Vespucci Airport (FLR) and rent a car for the duration of the trip. Most major rental car companies are available at FLR. Advance booking is recommended. If you are not renting a car, the Florence airport is about three miles from the town center. You can take a taxi (approximately €20) to the centre of town, or a bus which departs hourly. From Florence (Santa Maria Novella train station) there are frequent direct trains to Siena. The trip takes about 90 minutes and a one-way ticket costs about ten euros. Italian train schedules can be found on www.TrenItalia.com .

The trip takes place in the Tuscan countryside that is not well served by public transportation. For this reason, if you have not rented a car, we suggest you take a taxi ride from Siena to San Quirico d'Orcia. A private transfer from Siena to San Quirico takes about one hour and costs approximately €150. We suggest you contact our local driver ahead of time to arrange the transfer. Our Trip Consultant can provide you with our recommended local contact information.

Your Trek Travel host will meet you at your trip hotel Villa Liberty (Via Dante Alighieri 119, 53027 San Quirico D'orcia SI) at 11:00 AM on the first day of the trip. Depending on the number of guests booked for your departure date, it is possible we will ask you to shift your meeting time by approximately 30 minutes. Please have your riding gear readily accessible to avoid having to unpack your luggage. After a trip overview, you may change into your cycling gear where you will then be fitted to your Trek bike ensuring you will be comfortable for the week. Following a safety talk and a review of the details of the route, you'll begin the day's ride through the Tuscan countryside.

If you will be late for the meeting or are going to miss it altogether, please inform your host. If you cannot reach them, please call our hotel, Villa Liberty (+39 0577 899028) and leave a message with your expected arrival time and contact details.

Additional Departure Information

Your Trek Travel host will meet you at 11:00 AM at the trip hotel to take your bike and equipment before your departure. The hotel staff will be happy to reserve a taxi for you for Florence or other destinations. The trip to the airport in Florence takes approximately two hours. Please allow adequate connection time for any ongoing travel to accommodate possible traffic delays.

Day 1 Welcome to the rolling hills of the Val d'Orcia

Welcome to the rolling hills of the Val d'Orcia

Meet your Trek Travel host at your hotel, Villa Liberty, located in the heart of the medieval village of San Quirico d’Orcia. They'll give you a brief orientation of the adventures ahead and will fit you to your Trek bike, ensuring a comfortable ride for the week. Then, it's off on your self-guided bike tour in the enchanting landscape of the Val d’Orcia, famous for its unique and pristine views. Your first stop is the tiny medieval spa town of Bagno Vignoni, wh... Meet your Trek Travel host at your hotel, Villa Liberty, located in the heart of the medieval village of San Quirico d’Orcia. They'll give you a brief orientation of the adventures ahead and will fit you to your Trek bike, ensuring a comfortable ride for the week. Then, it's off on your self-guided bike tour in the enchanting landscape of the Val d’Orcia, famous for its unique and pristine views. Your first stop is the tiny medieval spa town of Bagno Vignoni, where you can dip your toes in the historic thermal springs and take pictures of the Roman baths located right at its center. Continue this scenic loop with a gentle climb up to Pienza, a UNESCO heritage site renowned for its pecorino cheese and considered one of the symbols of the Italian Renaissance. Wander through its streets and grab the best gelato in town at “Buon Gusto” before cycling back to your hotel at your leisure. Take some time to relax perhaps with a glass of wine in the garden and afterwards we suggest you walk to one of our favorite restaurants in the heart of San Quirico to enjoy your first Tuscan dinner! Read More

Villa Liberty

Meals included

Highlight of the Day

Visit Pienza

Stroll through this UNESCO heritage site with an ice cream in hand and get a photo of the valley below from one of the amazing viewpoints!

Ride Options

Ride Option 1

TODAY'S RIDE:

San Quirico to Bagno Vignoni to Pienza Loop - Approximately 19 mi | 30 km and 1,458 ft | 444 m

TODAY’S ACTIVITY:

Visit a Roman Thermal Spa Town

Day 2 Montalcino—the home of the famous Brunello DOCG wine

Montalcino—the home of the famous Brunello DOCG wine

This morning’s route lifts you high above the Val d’Orcia, a vista of rolling hills blanketed with vines and cypress trees. You'll ride up to Castiglione d’Orcia, admiring the remains of what was once the mighty Rocca Aldobrandesca, a fortress that dominates the village. Your first stop today will be the renowned Abbazia di Sant’Antimo, a monumental 12th-century Romanesque abbey, where if you're lucky, you may arrive to the haunting choral harmonies of the ... This morning’s route lifts you high above the Val d’Orcia, a vista of rolling hills blanketed with vines and cypress trees. You'll ride up to Castiglione d’Orcia, admiring the remains of what was once the mighty Rocca Aldobrandesca, a fortress that dominates the village. Your first stop today will be the renowned Abbazia di Sant’Antimo, a monumental 12th-century Romanesque abbey, where if you're lucky, you may arrive to the haunting choral harmonies of the monks' Gregorian chants. Your lunch destination is the walled village of Montalcino with its 14th-century fortress and steep cobblestone streets. Here you can discover the delights of Brunello wine, one of the finest Italian varietals, and enjoy lunch at your leisure at one of Montalcino’s many trattorias. When you're ready, cycle back to San Quirico along winding roads and relax at the hotel before selecting a local bistro in town from the list of Trek Travel recommendations. Read More

Discover the delights of Brunello wine

Brunello di Montalcino is considered to be one of the finest Italian varietals and your lunch stop in the walled village of Montalcino is th... Brunello di Montalcino is considered to be one of the finest Italian varietals and your lunch stop in the walled village of Montalcino is the perfect opportunity to taste it. Choose from one of Montalcino’s many trattorias where you can opt for a wine tasting on its own or paired with each course of your lunch! Read More

San Quirico to Montalcino Loop - Approximately 34 mi | 54 and 3,927 ft | 1,196 m

Ride Option 2

AVID OPTION:

San Quirico to Monticchiello to Montalcino Loop - Approximately 48 mi | 77 km and 4,822 ft | 1,470 m

Visit the Abbazia di Sant’Antimo

Day 3 Traverse the moonscape of the Crete Senesi

Traverse the moonscape of the Crete Senesi

Today you’ll head north following winding ribbons of road into gently undulating terrain into one of Italy’s most dramatic regions, the Crete Senesi. Here vineyards and olive trees give way to cultivated fields crossed occasionally by rows of cypress trees and a few solitary farmhouses. Riding here gives you a feeling of peace and, if you feel like adding some more mileage and elevation, take the avid route to Asciano, pedaling through meandering roads overlooki... Today you’ll head north following winding ribbons of road into gently undulating terrain into one of Italy’s most dramatic regions, the Crete Senesi. Here vineyards and olive trees give way to cultivated fields crossed occasionally by rows of cypress trees and a few solitary farmhouses. Riding here gives you a feeling of peace and, if you feel like adding some more mileage and elevation, take the avid route to Asciano, pedaling through meandering roads overlooking the surrounding ridges on an other-worldly route. We highly recommend you stop for lunch at our favourite restaurant in the tiny village of Montisi, Taverna da Roberto (please, make a reservation ahead of time). You'll be amazed by the passion and love he puts into preparing a delicious farm to table lunch for his guests! After lunch, continue your loop back to the medieval village of San Quirico d’Orcia where you can relax, perhaps with a spa session. The evening is yours to explore the cobbled streets of the town and to enjoy dinner at one of the many small bistros recommended by our local experts. Read More

Ride through the Crete Senesi moonscape

The Crete Senesi, the badlands of Tuscany, offer some of the most dramatic views of the week. The dramatic colors of this clay-dense soil ma... The Crete Senesi, the badlands of Tuscany, offer some of the most dramatic views of the week. The dramatic colors of this clay-dense soil makes it appear almost lunar. At once barren and stunning, the sprawling expanse of undulating fields will make you get off your bike to take a photo or to simply marvel at the natural landscape. Read More

San Quirico to San Giovanni d'Asso Loop - Approximately 25 mi | 40 km and 2,465 ft | 751 m

San Quirico to San Giovanni d'Asso to Asciano Loop - Approximately 43 mi | 69 km and 4,377 ft | 1,334 m

Experience Roberto's Slow Food Movement

Day 4 Discover Montepulciano, a charming town of rare beauty offering a "noble wine"!

Discover Montepulciano, a charming town of rare beauty offering a "noble wine"!

Enjoy your morning cappuccino before venturing out on a spectacular ride through the Val d'Orcia. Your destination today is one of Tuscany's prettiest towns, strung along a ridge at 605 meters above sea level and surrounded by walls and fortifications. Montepulciano is well known for its Renaissance buildings and churches, but it is especially renowned for its noble wine “Vino Nobile di Montepulciano"—simply divine! Stop for lunch in this elegant town and don't ... Enjoy your morning cappuccino before venturing out on a spectacular ride through the Val d'Orcia. Your destination today is one of Tuscany's prettiest towns, strung along a ridge at 605 meters above sea level and surrounded by walls and fortifications. Montepulciano is well known for its Renaissance buildings and churches, but it is especially renowned for its noble wine “Vino Nobile di Montepulciano"—simply divine! Stop for lunch in this elegant town and don't miss the opportunity of tasting its high-level vintage made from Tuscan Sangiovese grapes. There are plenty of wineries where you can sample it. After lunch, continue your ride at your own pace surrounded by idyllic cultivated hills. Back at the hotel in San Quirico, take some time to relax with a stroll in town soaking up the tranquil atmosphere of this ancient medieval village. Tonight, we suggest you dine at the local trattoria Il Vecchio Forno to celebrate a trip of a lifetime in a magical region of Italy! Read More

Visit Montepulciano

Stop for lunch at one of Tuscany's prettiest towns. Explore its medieval streets filled with beautiful Renaissance buildings and churches an... Stop for lunch at one of Tuscany's prettiest towns. Explore its medieval streets filled with beautiful Renaissance buildings and churches and taste its famous “Vino Nobile di Montepulciano." Read More

San Quirico to Montepulciano Loop - Approximately 32 mi | 52 km and 3,750 ft | 1,143 m

San Quirico to Torrita to Montepulciano Loop - Approximately 39 mi | 63 km and 2,765 ft | 843 m

Day 5 Rise early and watch the sun rise over the Tuscan countryside

Rise early and watch the sun rise over the Tuscan countryside

If you're up for it, close out your Tuscany self-guided bike tour by rising early for a final bike ride to Monticchiello as you watch the sunrise creeping over the classic Tuscan countryside. Or simply linger over a hot cappuccino and walk into town at your leisure, enjoying your final moments in this enchanting region. Your Trek Travel host will meet you at the hotel at 11:00 AM to take your bike and say farewell before you leave for Florence or other destinations.

Sunrise ride to Monticchiello

There's no better way to say farewell to your Tuscany Self-Guided Bike Tour than a sunrise ride. Wind your way up a quiet backroad to the hi... There's no better way to say farewell to your Tuscany Self-Guided Bike Tour than a sunrise ride. Wind your way up a quiet backroad to the hilltop village of Monticchiello to take in breathtaking views of Pienza and San Quirico and the surrounding hills. Read More

San Quirico to Monticchiello Return - Approximately 20 mi | 32 km and 1,494 ft | 455 m

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Rider Information

Rider Level: 3

Terrain: Hilly

The terrain is consistently hilly. Every day the routes will feature hills as many of the towns you stop at sit atop hills. The ascents are not exceptionally steep, however they are often upwards of five kilometers long, and along narrow and winding roads. Our Tuscany Self-Guided Bike Tour is best suited for our Level 3 Riders. For those eager to experience every mile but mindful of their physical limits, our electric bike option offers a comfortable and enjoyable solution. Level 4+ Riders will enjoy the extra mileage the avid route options offer.

Daily Average

26 miles | 42 kilometers

132 miles | 212 kilometers

2,432 feet | 741 meters

12,159 feet | 3,706 meters

There are a variety of non-riding options on this trip for riders who want to take the afternoon off or travel companions who want to spend little or no time in the saddle. Non-riders are welcome on a Self-Guided trip if they are staying in the same room with a riding guest. Non-riders will be offered a $500 discount from the trip price. Please contact a trip consultant for details and to book a non-riding companion. Some of these options may need to be scheduled before your trip—please contact one of our Trip Consultants for more information. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:

• Shop and explore the medieval villages of Pienza , San Quirico, Montalcino, and Montepulciano
• Relax by the pool in the hotel's beautiful gardens
• Stroll through quaint medieval villages
• Enjoy a wine tasting of the renowned Brunello wine in the heart of Montalcino
• Experience an olive oil tasting tour
• Take a traditional Tuscan cuisine cooking class

On a self-guided tour you need to feel comfortable changing a flat, as this is a common event when cycling. All self-guided trips include Ride With GPS, which is like having a personal guide in your pocket! You'll get turn-by-turn directions and recommendations from Ride With GPS, plus the you'll have the added navigation support of a Garmin GPS. In the rare case of a bicycle breakdown or mechanical issue beyond a simple repair, your Ride With GPS app will have detailed contact information with emergency phone numbers to call for assistance. Learn more about our Self-Guided Bike Tours .

• Up to three daily route options
• Ride With GPS app loaded with emergency phone numbers and local suggestions
• Pre-loaded routes on a Garmin GPS

Villa Liberty is an elegant 4-star boutique hotel set in an ancient Renaissance villa with bright and spacious communal areas. The rooms are a perfect blend of Tuscan tradition and modern luxury, decorated with exclusive works of art. Instead of a fully dedicated wellness area, the spa’s features are scattered throughout the property in the heart of charming San Quirico d’Orcia. There is also access to a wonderful outdoor pool surrounded by tranquil gardens where you can relax after the ride. Breakfast is served at the hotel’s own traditional trattoria “Al Vecchio Forno” within short walking distance from the accommodation.

Bikes & Gear

Trek Domane SL 7 Gen 3

Trek’s continuous innovation has led to one of the best bikes on the road – a light weight, stable, and technologically advanced machine to make even the hardest roads seem easy. The Domane SL 7 Gen 3 is a beautiful high-performance endurance road bike with wireless electronic Ultegra Di2 12-speed drivetrain for lightning-fast precision shifting in any conditions. The combination of the carbon frame with front and rear IsoSpeed, carbon wheels that come stock on the bike, and hydraulic disc brakes keep it smooth, safe, fast, and most importantly, fun!

Trek Electric-Assist Verve+

Fun from the first pedal stroke, our e-bikes give you the boost you want to venture further on your bike tour. With its low-step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain, with energy to spare.

Additional Gear

• Trek Travel water bottles to keep
• Bontrager saddle
• Bontrager helmet
• Bontrager front and rear Flare R lights
• Garmin Edge 830 or 1030 GPS computer with pre-loaded routes
• Shimano SPD-SL road style pedals, Shimano SPD mountain style pedals, caged, or flat pedals
• A flat pack containing a tube, levers, and a CO2 cartridge with inflator
• For the most comfortable ride, we recommend you bring your own saddle. If you prefer, you can bring your own pedals and helmet on the trip and your host will install your gear on the first day during your bike fit.

Trip Inclusions

• Four nights of accommodation at one handpicked hotel
• Daily breakfast
• Daily lunch and dinner recommendations
• Up to three daily route options on riding days
• A bike lock, all necessary chargers and a floor pump
• Bike fit on the first day to help you find your optimal riding position
• Ride With GPS Experience on your phone to get all the information you need on your self-guided adventure

• Airfare and transportation to and from the trip meeting/departing locations
• Lodging before and after the trip
• Personal items purchased during the trip
• Optional activities not scheduled by Trek Travel
• While we provide daily breakfast, the other meals are not included. On self-guided trips, Trek Travel provides restaurant recommendations and invites you to explore the local cuisine at your leisure
• Trek Travel jersey's are not included on our Self-Guided bike tours but they are available for purchase. Visit our Trek Travel Online Shop to see your options.

Guide Gratuities

For self-guided bike tours you are welcome to thank your host (preferably in the local currency) with a gratuity based on their level of professionalism and service.

Additional Details

Your Day. You Decide.

Our self-guided vacations are designed to fit all types of travel styles. Whether you like to spend your time relaxing or on a non-stop adventure, you get to decide what your day looks like. Choose your mileage, itinerary, and experience level and leave the rest to us!

Your Trip Need to Knows:

• We do our best to avoid busy roadways as much as possible, however, urban riding and sections of busy roads are unavoidable for some segments of your rides.
• It’s a good idea to carry cash when visiting some of Tuscany’s smaller villages and for paying for small items like coffee. You’ll be amazed at the quality of coffee you can get for just a few euros.
• Expect slower service in restaurants and cafés in Tuscany. Be aware that meals usually take a little longer and are traditionally multiple courses.

Before and After Your Trip

Siena, Italy

One of Italy's medieval jewels, Siena is a labryinth of rambling red-brick lanes. Siena's heart is its central piazza known as Il Campo, a shell-shaped square dominated by the red Palazzo Pubblico and its tower, Torre del Mangia. Admire it from below or climb over 500 steps to the top to enjoy a wonderful view—this is one stop you don't want to miss in Siena. Piazza del Campo is known worldwide for its architectural beauty and its particular "shell" form. Another unmissable highlight is the stunning Gothic Duomo full of treasures, including its marble pavement, Piccolomini library frescoes, and incredibly ornate interiors. We recommend the following accommodations for your pre-trip hotel:

Where to Stay

Hotel Athena

This 4-star hotel is nestled among the heart of the old town, with the cathedral and Piazza del Campo only steps away. It has been designed with luxury and rustic sensibility in mind, as each room comes equipped with a range of modern amenities. Enjoy panoramic views of the Tuscan countryside from a rooftop terrace adjacent to the hotel bar. www.hotelathena.com

Grand Hotel Continental Siena

Set in a 17th-century building, this luxury 5-star hotel is located in the historical center of Siena, 250 meters from Piazza Campo square. It offers elegant rooms with frescoed ceilings and period furnishings. With treasured artwork, rooms and suites feature porcelain and Travertine marble details, and original Tuscan terracotta floors. The elegant Sapordivino restaurant offers gourmet traditional cuisine, while at the Lounge Bar by Sapordivino guests can enjoy an aperitif or cocktail. www.starhotels.com

Palazzo Ravizza

This historic 3-star hotel is a family-run property in the heart of Siena, offering elegant rooms with characteristic 1920s furnishings. All rooms are different in size, and furnishings vary from frescoed walls or ceilings to terracotta floors. Some rooms have views of the garden or the hills surrounding Siena. www.palazzoravizza.com

Florence, Italy

Florence is the majestic heart of Renaissance art and intellect. Several days can be spent wandering the streets in the shadow of Brunelleschi’s Duomo and strolling beside the Arno. Along with the Duomo and Ponte Vecchio, the Uffizi gallery, a pillar of the Renaissance and Medici eras, merits a visit. Michelangelo's David in the Galleria dell'Accademia is not to be missed. Keep in mind while exploring Florence that opening hours vary and are quite often inconsistent. Different museums are open on different days and lines can be very long. It’s worthwhile to pay a few extra euros and pre-book your tickets—this will enable you to bypass long lines of visitors at the entrances. We recommend the following accommodations for your post-trip hotel:

Eurostars Florence Boutique

This boutique hotel is a true masterpiece of hospitality, a historic palazzo restored and converted into a 4-star hotel, just 50 steps from the River Arno and a 10-minute walk into the heart of Florence. Discover the magic of Florence on two wheels with their fleet of Trek bikes or admire stunning city views from the rooftop terrace. www.eurostars-florence-boutique.com

Hotel Il Guelfo Bianco

This patrician home of the 16th century is close to the old market in the heart of downtown Florence, just a short walk to the Cathedral and principal museums. This 3-star hotel recently re-opened its doors to guests after having undergone a complete restoration. The Renaissance architecture and the refined furnishings reflect the Florentine character. www.ilguelfobianco.com

Hotel Montebello Splendid

The Hotel Montebello Splendid is an elegant 5-star, boutique hotel located just 10 minutes walk from all the main monuments and points of interest in Florence. Take advantage of their concierge services to plan your stay in Florence to the last detail. www.palazzomontebello.com

Average monthly temperature and precipitation

Packing and Weather

Spring and fall in Tuscany are usually clear and sunny, with warm daytime temperatures (75-90ºF/24-32ºC) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Summers are hotter with higher daytime temperatures (80-95ºF/27-35ºC) and evening temperatures 10 degrees cooler. Rain is always a possibility, so be prepared with wet-weather gear in order to best enjoy your vacation. View our Packing List

Ready to book?

To reserve your space on a trip, you can either call us at 866-464-8735 to speak with an expert Trip Consultant or book online any time by clicking the “BOOK THIS TRIP” icon near the upper right of each destination’s overview page.* Once you have submitted your reservation online, a Trip Consultant will contact you within one business day to answer any questions you may have and to confirm space, bike, and room availability on your desired trip. Your booking will be finalized once your no-risk deposit is paid. If you make a reservation more than 90 days prior to the trip, a $750 no risk deposit is due at the time of booking.** If you reserve your trip less than 90 days prior to the departure, the full balance is due at the time of booking. Once your booking is complete you will receive an email confirmation with important information pertaining to your trip.

*Please note that select trips cannot be booked online at this time. For those trips, please call a trip consultant at 866-464-8735.

**Deposit amounts vary for all Race, Cross Country, Special Edition, Ride Camp, Discover, and Self-Guided tours. Please confirm deposit amounts for all trips with your Trip Consultant at time of booking.

What happens once I book?

When a trip is booked, a guest confirmation letter is immediately sent out. One week prior to the trip start, you’ll receive an email containing your trip start meeting location reminder and any last-minute information that you’ll need to know before you go. Once you arrive at your destination, your Trek Travel host will brief you on the day-to-day plan for the trip and give you an overview on the daily route information and detailed maps within the Ride with GPS app. Your host will also review with you the preloaded Garmin GPS computer that allows you to ride with complete confidence and independence.

What if I have to cancel my trip?

We understand things happen in life and sometimes you have to cancel or change your self-guided bike tour. We want to make it as easy as possible to do so and below you’ll find our timeline.

Have a question? Just give us a call, 866-464-8735. Read our Cancellation Policy

Travel Protection

Trek Travel recommends that you purchase a travel protection plan to help safeguard you and your travel investment against the unexpected. We offer a travel protection plan through Arch RoamRight that provides coverage for unforeseen events that could affect your ability to travel with us. Learn more about our Travel Protection

Travel Services

We've collaborated with a specialized travel agency committed to delivering tailored vacation planning, ensuring your entire Trek Travel journey is nothing short of unforgettable. Learn more about our Travel Services

Single Supplement

Your Self-Guided trip price is per person based on two guests sharing a room. If you are a solo traveler or if you want to stay in your own private room while traveling with other people, you will have a Single Supplement Fee added to your trip price at the time of booking.

General Self-Guided FAQs

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to the most common questions that don't necessarily pertain to a specific trip. See Self-Guided FAQs

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Guaranteed trips.

Our trips are guaranteed to run once we have one confirmed booking on the trip.  Click here to view our full guarantee policy .

Trek Travel reserves the right to cancel trips with zero guests, therefore you must book with Trek Travel before making travel arrangements for the trip. We are not responsible for travel arrangements made prior to confirming your Trek Travel Trip. Select trips are not guaranteed.

Sold Out/Waitlist

This trip is currently sold out, but you may be added to the waitlist in the case of availability.

If a date is marked with Limited Availability, there are few spots left to book. We will secure additional rooms from our hotels before confirming your reservation.

Looking to travel with a small group? Ask our trip consultants about private trips and learn more .

What are your trip styles?

Classic - reserve:.

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discovor:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Train like the pros in some of their favorite riding destinations.

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.

Enjoy a bike tour on your schedule with just your chosen travel companions.

If a date is marked as Private, it is reserved for a private group.

Looking to travel with a small group or looking for a custom date? Call our trip consultants at 866-464-8735

What is the Difference?

Ultimate luxury:.

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.

Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.

These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.

On select cycling vacations, you’ll stay at a mix of hotel levels, from Explorer to Luxury to Ultimate Luxury. Rest assured, no matter which level of hotel you’re at, our trip designers carefully select every accommodation.

Road : 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).

Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).

Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).

Road : 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).

Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).

Road : 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).

Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).

Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).

Road : 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).

Gravel: 3-5 hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).

Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).

Single Occupancy

Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself

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Bicycle Tours — Italy

Tuscany Gravel - The White Roads of L'Eroica

Self-guided - val d’orcia to gaiole in chianti - 7 days.

• Dates & Prices

Strade Bianche means 'white roads' in Italian, named after the limestone gravel turning into white dust on the famous racecourse of L'Eroica, now famous among gravel cyclists around the world. These iconic Tuscan roads boast steep climbs, fierce attacks, and breathtaking vistas, making it a must-visit for gravel cycling enthusiasts, as well as for bicycle travelers who prefer quiet, unpaved backroads. On our self guided bike tour itinerary, you'll experience some of the routes of L'Eroica, carefully selected as part of our unpaved and gravel roads itinerary. You'll also discover the marvelous scenery, famous wines, and exquisite picturesque medieval towns that make Tuscany famous.

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Pienza & Montefollonico

Highlights: Rennaissance Pienza, Bike fitting and test ride, Montefollonico

Meet and greet in Pienza. Known in Italy as "the purest renaissance town", Pienza is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets. For those arriving early enough in the afternoon, you can go on a test bike ride to Palazzo Massaini and Montefollonico. Daily Distance: 25km (15 miles) - 12 km asphalt and 13 km gravel Elevation Gain: +558/-565 m (+1837/-1854 ft) Accommodation: Relais Il Chiostro di Pienza , or similar.

Montepulciano & Bagno Vignoni loop ride

Highlights: Val d'Orcia, Montepulciano, Monticchiello, Bagno Vignoni

Your tour starts with a loop ride from Pienza. Spring brings red poppy blossoms to the vibrant green wheat fields of Tuscany, and nowhere is the bloom more brilliant than the hills of the Val d’Orcia, a UNESCO World Heritage Site. As we pedal through these corridors of proud cypress trees, the scenery may look familiar from such films as Gladiator and The English Patient. Follow the gravel tracks off the beaten path through a timeless slice of Tuscany. You'll come to hilltop Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. Enjoy the lovely, picturesque lanes of this hilltop medieval town, before setting off on a breathtaking and challenging gravel section that brings you to Monticchiello, the quintessential Tuscan hill town. Back in the valley, the next destination is Bagno Vignoni, a thermal spa town that dates back to Roman times. Be sure to visit the Madonna di Vita Leta chapel on the way back to Pienza. Daily Distance: 52km (32 miles) - 17 km asphalt and 34 km gravel Elevation Gain: +872/-875 m (+2861/-2871 ft) Accommodation: Relais Il Chiostro di Pienza , or similar.

Cycle Pienza to Montalcino

Highlights: Pieve a Salti, the lands of Brunello wine, Montalcino, Lucignano d'asso

To get from Pienza to Montalcino we've selected the sections of L'Eroica called Lucignano d'asso and Pieve A Salti. You leave Pienza and after 6 km of pavement, the white roads begin toward Cosona and reach the little hamlet of Lucignano - a caffe espresso at Emporio bar is a must here! Once you reach the paved road you ride only one km and start the other Eroica gravel section known as Pieve a Salti, where you'll be surrounded by beautiful Tuscan rural landscapes. We recommend lunch in Buonconvento, where you'll prepare for the famous climb to the famed wine town of Montalcino, a total of 10 km (half paved, half gravel) through enchanting vineyards and wineries. Once in town we suggest a visit of the hilltop fortress dominating the valleys below, where you'll be provided breathtaking views of the routes you've cycled today. Daily Distance: 41km (26 miles) - 17 km asphalt and 24 km gravel Elevation gain: +855/-807 m (+2805/-2647 ft) Accommodation: Hotel Giglio , Vecchia Oliviera , or similar.

Cycle to Siena

Highlights: Castiglione del Bosco, Siena, Passo del Lume Spento

L’Eroica—meaning “The Heroic”—is a celebration of the golden age of cycling. The event takes place every October when thousands of hardened cyclists travel back in time to ride these gravel roads on primitive machines of the past. The heavy lugged-steel bikes with down-tube shifters and impossible gear ratios are no match for the red wine in the participant’s water bottles and the racer's spirit. Today, we’ll have our own taste of cycling’s heroic origins as we join one of the most beautiful gravel sections of L’Eroica. From the heart of Brunello di Montalcino, Tuscany’s most celebrated wine region, ride to the top Passo del Lume Spento. Wonderful gravel cycling continues, arriving at Castiglion del Bosco, the biggest brunello winery and farm, which belongs to Ferragamo, the famous Italian fashion designer. Once in Bibbiano, you'll tackle the Piana section and and reach Murlo, another caffè stop must! Shortly you will face another legendary Eroica section to Radi, with some steep yet short ups and downs. At Ville di Corsano you deserve a light lunch. From here you have the last 12 km on secondary paved roads to marvelous Siena, one of the highlights of the tour. Daily Distance: 56km (35 miles) - 32 km asphalt and 24 km gravel Elevation gain: +1015/-1229 m (+3330/-4032 ft) Accommodation: Villa STR , or similar.

Gaiole in Chianti, the Eroica town

Highlights: Gaiole, Chianti vineyards, Siena

Today's destination is starting point of the Eroica race. After breakfast, head out into magical land of Chianti. Exiting Siena via an Eroica gravel section, making your way through wheat fields before entering the vineyards of this celebrated wine region. After reaching Pianella, you'll being a long, glourios section to Canonica a Cerreto, Vagliagli, always cycling through Chianti Classico vineyards, counting castles and old hilltop hamlets! You'll make it to Radda in Chianti for lunch time after cylcling gravel most of the day. From Radda, it's only 8 km to Gaiole still on the Eroica itinerary, including the breathtaking landscsapes near San Donato in Perano and Vertine. Daily Distance: 46km (29 miles) - 16 km asphalt and 30 km gravel Elevation Gain: +923/-874 m (+3028/-2867 ft) Accommodation: Castello di Spaltenna , or similar.

Chianti hills and Castello di Brolio loop ride

Highlights: Chianti Senese hills, Castello di Brolio, Castelnuvo Berardenga

On today's loop ride you'll explore the villages and hamlets of the Chianti Senese region. Start from "your" Spaltenna castle in Gaiole, reaching Castello di Brolio afer 10 km, a joyous cappuccino stop, after which you'll get on gravel sections of L'Eroica. Castelnuvo Berardenga, San Gusmé, and Villa a Sesta, are some of the small Tuscan hamlets you'll cross on today's glorious ride. On the return to Gaiole you'll have two options, including a challenging uphill to Castagnoli. Daily Distance: 54km (34 miles) - 44 km asphalt and 10 km gravel Elevation Gain: +1013/-1012 m (+3323/-3324 ft) Accommodation: Castello di Spaltenna , or similar.

Tour ends in Giaiole in Chianti

Highlights: Badia a Coltibuono optional ride

If you are feeling stronger and full of energy at this point, this morning you can tackle a 20km loop ride to Badia a Coltibuono, ending back in Gaiole where you will leave bikes. Or choose to end your tour after breakfast. Frequent buses to Siena are available, from where you can take fast train to your next destination. Daily Distance: optional 21km (13 miles) Elevation Gain: +395/-420 m (+1296/-1378 ft) PLEASE NOTE : The final itinerary, including hotels and/or activities described here, are subject to changes according to availability. City hotel taxes are not included.

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