A cyclist riding towards the camera on a white gravel road
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Bruschetta in Tuscany
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A cyclist riding towards the camera on a white gravel road 23TCG_GCORDINI_A7C00347x-1600X670 23TCG_GCORDINI_DSC06139x-1600X670 23TCG_GCORDINI_A7C00286x-1600X670 23TCG_JBonnamour - 46-1600X670 23TCGL-Tuscany-Gravel-1600X670 - 23TCG_Hotel-Capanna-esterni2-1600X670 23TCG_JBonnamour - 23-1600X670 Bruschetta in Tuscany 23TCG_GCORDINI_DSC06229x-1600X670 23TCG_JBonnamour - 19-1600X670

Tuscany Gravel Bike Tour

Ride the Famed White Roads of Tuscany

Our Tuscany Gravel bike tour is brimming with amazing rides, and the culinary delights, history and classic beauty that make this region famous. Tuscany’s limestone gravel roads are deeply intertwined with Italy's heritage. This legendary countryside brims with the kind of pure delights that awaken your senses. Your eyes stare in disbelief at sun-drenched, rolling vistas speckled by cypress trees and endless vineyards. Everything comes alive with the fragrant smells of olives and those deep Chianti reds. Your taste buds will indulge in rich pastas, pizzas, and all the great wines of the region. This is everything you imagine from a Tuscan vacation, but so much more as we get off the grid and onto a gravel adventure fit for royalty. You'll ride on timeworn white gravel roads, known as the strade bianche, that set the stage for Italian pro races of today and eras past, into the Crete Senesi with its stunning other-worldly views, and over to the scenic Val d’Orcia. Discover the quintessential Tuscan villages of Gaiole, picturesque Montalcino, and the most regal of them all — Siena. This is the ultimate Tuscan unpaved adventure you won’t want to miss. Book your trip with confidence »
Learn if a Gravel trip is right for you »
Tuscany Gravel Bike Tour
$3299 Per Person
5 Days & 4 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Hotel Level: ?
From $3299 per person View All Details
Trip Wows
Pedal on the same hilly paths as the historic and famous bike events the region is known for
Taste superb Tuscan wines and world-recognized Brunello di Montalcino
Stay in a 16th-century transformed village that today is a luxury destination in the heart of the Tuscan countryside
Explore white gravel roads — the strade bianche — lined with cypress trees and immerse yourself in Italy’s less-traveled paths
Discover the charming, medieval towns of Montalcino, San Quirico, and the historical center of Siena as well as the UNESCO World Heritage site, Val d'Orcia
Tuscany Gravel Bike Tour
It is an incredible journey to discover the hidden corners of the Tuscan territory. Nothing is like the "white roads" of Tuscany; perfect for cycling, quiet, picturesque, rich in history, and ready to host cyclists, whether it's a pro race or an historical re-enactment. At the top of each new hill, I am rewarded with unique, postcard scenery. The atmosphere that you breathe is one of a kind, the people are cheerful and light-hearted and never refuse a good glass of Chianti or Brunello.
-Giorgio, Trek Travel Guide

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price is guaranteed.
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Single Occupancy from: +$899
Apr 29 – May 3 
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May 13 – May 17 
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May 27 – May 31 
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Jun 10 – Jun 14 
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Aug 26 – Aug 30 
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Sep 2 – Sep 6 
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Sep 16 – Sep 20 
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Sep 23 – Sep 27 
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Sep 30 – Oct 4 
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Oct 7 – Oct 11 
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Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

You'll meet your guides in Florence, a marvel of Renaissance art and where you'll find the Uffizi galleries, the Duomo, and the Galleria dell'Accademia, home of Michaelangelo's David. From here you'll take a one-hour private shuttle to the charming town of Villa a Sesta. After a delicious Tuscan, picnic-style lunch, you'll be fit to your Trek Checkpoint gravel bike, and then we're off on a rolling, scenic ride through stunning cypress trees and to the impressive Abbadia a Monastero, a monastery dating back to the 9th century. We'll arrive at our hotel where you can relax, unpack, and prepare for our first night's dinner and social hour at the hotel.

Today's Ride:

Monastero d'Ombrone Loop
Approximately 16 mi | 26 km and 1,180 ft | 360 m


Villa Curina Resort

Included Meals:

Lunch | Social Hour | Dinner

Buongiorno! We arise in Chianti with an appetite for a hearty breakfast and a menu of adventure. Today you will cover some of the most beautiful roads in the area. After a brief warmup on the pavement, you'll turn onto the gravel roads toward the historic, medieval towns of Vagliagli and Radda. In centuries past these limestone-white, unpaved roads, known by their Italian name strade bianche, were the only connections between those villages! We'll stop for lunch at a cafe of your choosing in Gaiole, a small Tuscan village with a unique history of vintage cycling. Don’t miss a visit to the Eroica cycling store to learn more and pick up a souvenir and signature caffè latte. After lunch, we'll continue winding through fragrant vineyards to the cypress-lined entrance of Castello di Brolio, the famous castle that has been the home of the Ricasoli family for 800 years. The afternoon is yours for relaxing at the hotel before we gather for a chef-inspired pizza dinner in the evening.

Today's Ride:

Radda to Gaiole Loop
Approximately 40 mi | 64 km and 3,900 ft | 1,200 m

Short Option:

Radda to Gaiole with Shuttle
Approximately 24 mi | 38 km and 2,560 ft | 780 m

Avid Option:

Radda to Gaiole to Castelnuovo Loop
Approximately 48 mi | 78 km and 4,750 ft | 1,450 m


Villa Curina Resort

Included Meals:

Breakfast | Dinner

It's another spectacular day of cycling discovery and adventure as you follow the white gravel routes featured in one of Italy’s most famous pro races, taking you to beautiful Siena, the start and finish point to the race. In this picturesque town you can enjoy the views while sipping your macchiato in the vibrant Piazza del Campo, Siena’s main historic square and local meeting point. From Siena, you'll head south through the almost lunar landscape of Crete Senesi to Buonconvento, where we'll stop for a special lunch with incredible, sweeping views of Tuscan rolling hills. With 360 degree vistas, you can appreciate the contrast between the dense vineyards of Chianti and the vast, rolling fields of Val d'Orcia. We arrive this afternoon at our destination, an elegant luxury agriturismo, that has a unique perspective on the traditions of this beautiful region. Tonight, your guides will shuttle you to the nearby walled fortress of Montalcino for a dinner of your choice.

Today's Ride:

Villa Curina to Buonconvento with Shuttle
Approximately 30 mi | 50 km and 2,620 ft | 800 m

Avid Option:

Villa Curina to Siena to Capanna
Approximately 37 mi | 60 km and 3,200 ft | 1,000 m


Capanna Suites

Included Meals:

Breakfast | Lunch

Rise today with a cappuccino in preparation for some of the region's most stunning views. Our ride today takes us to the hills of Val d'Orcia. The Val d'Orcia is an incredible agricultural landscape that is a UNESCO World Heritage site due to its continued adherence to Renaissance layout and aesthetic. It is like cycling inside a painting! You'll continue through the medieval villages of San Quirico d’Orcia and Pienza, with buildings dating to the 15th century and epic views from every hilltop. Don't forget to stop and savor the scenery and maybe even take a few pictures before we head back to the hotel. Tonight, we celebrate a week's worth of memories with a special dinner prepared with seasonal ingredients sourced straight from the hotel farm and perfectly paired with select local vintages. We'll toast together and recap the highlights of an incredible week!

Today's Ride:

Pienza to Lucignano D'Asso Loop
Approximately 38 mi | 61 km and 3,900 ft | 1,190 m

Short Option:

Pienza to Lucignano D'Asso with Shuttle
Approximately 25 mi | 40 km and 2,600 ft | 790 m

Avid Option:

Capanna to Lucignano D'Asso Loop
Approximately 44 mi | 70 km and 4,270 ft | 1,300 m


Capanna Suites

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

It's sadly time to say farewell to this Signature Tuscan unpaved adventure. Choose to rise early for one last glorious spin at the base of Montalcino through lush, fragrant vineyards as a warm sun rises over the Tuscan countryside. Or, skip the ride and savour a cappuccino at the hotel, recounting the memories of a week well-spent. However you say goodbye to the sumptuous heart of Italy, you'll be sure to take a small bit of it in your soul as you leave.

Today's Ride:

Brunello Loop
Approximately 9 mi | 14 km and 780 ft | 240 m

Included Meals:



hotel image

Villa Curina Resort

Castelnuovo Berardenga, Italy

Explorer Accommodation | Set peacefully in the countryside, surrounded by the verdant hills of Chianti and just a few kilometres from Siena, this charming hotel has it all, including rich sunset views; incredibly romantic, well-appointed and individually decorated rooms; a refined, elegant restaurant; and beautiful gardens that surround the entire property, all encompassed in a 16th century hamlet that has a long and rich history.
hotel image

Capanna Suites - Agriturismo, Spa, & Wine Club

Montalcino, Italy

Luxury Accommodation | Capanna Suites is a unique luxury destination - a boutique agritourismo offering true immersion in the local terroir to understand the path of the grape to your glass, and the farm to your table. Room designs explore the perfect balance of rustic chic. Enjoy the modern amenities and high-quality materials that help create an incredibly comfortable stay. It's also a beautiful introduction to Brunello wines in the Montalcino region, as you decompress and enjoy the best in food, accommodations, and optional spa treatments.

What's Included

For us, the details matter most

Every moment of our Trek Travel Tuscany bike tour has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Checkpoint SLR 7

Take on the challenge of gravel with the knowledge that you are riding the best gravel bike in the business. With a high performance frame designed to be nimble yet stable, and the smoothing effect of rear IsoSpeed technology, it will let you ride with ease on any type of surface. The rugged drivetrain allows you to enjoy smooth and reliable shifting no matter the terrain. It also features Shimano hydraulic disc brakes for predictable and safe stopping power wherever you go. The 45mm tubeless gravel tires will give you confidence to tackle any bump in the road. If you want to escape the concrete, and adventure unpaved, let this bike take you there. Learn More


Trek Electric-Assist Domane+ SLR 7

Take the tailwind with you and leave your limits behind on the all-new Domane+ SLR 7. With a groundbreaking ratio of ultra-lightweight design and electric assist, Domane+ SLR 7 has everything you love in a road bike, with the extra boost to take you farther than ever before. This performance e-road bike will help you on the climbs, hang with the fast group, and venture further on your cycling vacation. So go ahead – take the long way. With Domane+ SLR 7, there’s always room for more distance, more speed, and more fun! Upgrade to the Domane+ SLR 7 on this trip for $399 (3-6 day trips) or $599 (7+ day trips). Available in limited quantities. Please contact a Trip Consultant to check availability. Learn More


  • Four nights of accommodation at two historic hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, three lunches, and three dinners
  • Two social hours of drinks and hors d'oeuvres
  • Ride a Trek Checkpoint SLR 7
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Santini cycling jersey to keep
  • Trek Travel water bottles to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, a flat pack (containing a tube, levers, and a CO2 cartridge with inflator), front and rear Bontrager Flare R lights, a Bontrager saddle, and Shimano SPD mountain style pedals
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your trip
  • A digital photo album of your trip
  • Entrance fees for all activities, private tours and events


  • Upgrade your ride to the Trek Electric-Assist Domane+ SLR 7 specially outfitted with 40mm Bontrager GR1 tires (+$399, subject to availability.)
  • Trek Checkpoint SLR 7 carbon gravel bike with Shimano GRX electronic shifting and Bontrager carbon wheels
  • Tubeless Pirelli Cinturato Gravel M tires, size 45 mm
  • Trek Travel Santini cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano SPD mountain style pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • In-frame storage containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Guide gratuities are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this Signature Gravel trip, we suggest a tip for your guides between $200-$250 per guest and, of course, you may choose to give more if your guides made your trip an unforgettable experience. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or our staff can help before or after the trip. Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the bike trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

43 kilometers / 27 miles
215 kilometers / 133 miles
755 meters / 2,476 feet
3,773 meters / 12,380 feet
The unpaved surfaces on our Tuscany Gravel bike tour are rated as Intermediate. About 50% of the riding is unpaved. You can expect primarily well-made, smooth dirt roads with small, sparse to moderate amounts of gravel, including the well-known white gravel roads known as the strade bianche. At times, there will be short sections of rougher road that may have chunky gravel as well as some potholes, ruts, or washboard surfaces, however there is always enough room to pick up a different line or go around obstacles. This trip covers Chianti and Crete Senesi areas of Tuscany. The terrain is a mixture of rolling hills and short, steep hills to keep you on your toes. On some days you will ride 4-8 miles (6-12 kilometers) of pavement before you reach gravel. Once on gravel roads, expect minimal traffic and no services as you will be traversing rural agricultural land. Your guides will be able to drive all roads with the support van. Our Tuscany Gravel Bike Tour is best suited for Type 3 Riders who have experience riding gravel roads and are accustomed to hilly terrain. Type 2 riders who are comfortable riding gravel but are looking for less mileage can ride the short options and utilize the shuttles as indicated. Type 4 Riders will enjoy the extra mileage and climbs the avid route options offer. If you have gravel experience but are concerned about your physical ability to conquer the mileage and elevation, you may want to try our Domane+ electric-assist bike option.
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. Some non-riding options during on our Tuscany Gravel bike tour are:
  • Shop and explore the medieval villages of Radda, Montalcino, Pienza, and San Quirico
  • Spend a day in Siena, take a historical tour or enjoy restaurants and shopping
  • Relax at local spa and pool
  • Wine and cheese tasting in Montalcino
  • Discover walking trails of the Val d'Orcia, a UNESCO World Heritage site

See itinerary for specific daily ride distances and elevation options. This is a Signature Gravel trip. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. On our gravel cycling vacations, Trek Travel seeks to find well maintained, non-technical gravel roads and bike paths; unmaintained roads and roads with ruts or deep or chunky gravel are avoided as much as possible. However, gravel roads are dynamic by nature. Road surfaces change throughout the year depending on maintenance (grading, adding new gravel) and weather, particularly rain. Our guides will be constantly monitoring road conditions and may change the routes as needed to provide the best possible riding experience. In addition, as with all of our trips, at times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our Today’s Ride options.

Travel Details

How to Get There

Florence Airport (FLR)
10:30 AM
Via Fiume, 12, 50123, Florence, Italy

Say Farewell

Florence Airport (FLR)
12:30 PM
Via Fiume, 12, 50123, Florence, Italy


We suggest that you arrive at least one day prior to the start of your Tuscany bike trip, 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 the Florence Airport (FLR).The airport is about three miles from the town center. You can take a taxi (approximately 20 euros) directly to the hotel, or a bus which departs hourly.

You can also fly into Rome or Milan and take a train or flight from either city. From Rome’s Fiumicino Airport (FCO), you may take a direct train to Rome’s central station, Roma Termini. Follow the “Stazione/Railway Station” signs. Trains depart twice hourly. Tickets can be purchased at a Biglietteria office or from ticket machines. All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform. The ride takes 30 minutes. From Roma Termini, transfer to a train for Florence. The Eurostar trains depart frequently and are the quickest. The trip takes one and a half hours and costs between 44-62 euros one way per person. In Florence, taxis are available to take you to your hotel. Taxi service is available from Rome Fiumicino Airport to central Rome for around 50 euros. For information about travel through Milan’s Malpensa Airport (MXP), consult the website www.airportmalpensa.com.

Your Trek Travel guides will meet you on Via Fiume, 12, 50123, Florence, Italy, in front of the Hotel Albani at 10:30 AM on the first day of the trip. Please wait here to meet your Trek Travel guide. You’ll then shuttle 90 minutes to your lunch spot for a taste of Tuscan cuisine. After lunch, your guides will do a bike fitting to ensure your comfort on your Trek Checkpoint SLR 7 this week, before you take your first spin through the countryside. Please have your first day’s riding gear handy and separate from your other luggage to facilitate the bike fitting and ride.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip starts with their names and contact details. If you cannot reach them, please call our first hotel, Villa Curina Resort in Castelnuovo Berardenga (+39 0577 355630) and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel in Villa Curina Resort for approximately 150 euros. The trip takes over an hour from the center of Florence.

View our pre hotel recommendations


You will say farewell to your guides at 11:00 AM at your final hotel, Capanna Suites in Montalcino. You’ll depart by private shuttle to Hotel Albani, Florence, arriving at around 12:30 PM. The hotel is a 5-minute walk from Santa Maria Novella train station where trains connect to many European cities. Please do not book seats before 1:30 PM, allowing adequate connection time for any ongoing travel or possible traffic delays. The airport in Florence (FLR) is three miles from the city. You can reach it by train, taxi, or shuttle bus; please do not schedule a flight prior to 4:00 PM. Visit www.TrenItalia.com for train information.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Spring and fall in Tuscany are usually clear and sunny, with pleasant daytime temperatures (70F-85F/21C-29C) and evening temperatures 10-15 degrees cooler. A jacket will be useful in the evening. Rain is always a possibility, however, so be prepared with wet-weather gear and warmers in order to best enjoy your cycling vacation. Packing List

Before and After Your Trip


Before: 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. Michelangeo’s David in the Galleria dell’Arte 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 pre-trip hotel:


After: Rome, Italy

Rome is a powerhouse of stunning architecture and ancient history, beautifully told through its ruins and buildings. It seems that every street you walk down provides another unexpected glimpse of ancient times, yet modern bustle and energy abounds as well. The Coliseum, the Forum, Vatican City, and the Pantheon are some of the must-see attractions. Be sure to linger on the Spanish Steps one afternoon and take advantage of great shopping and fantastic cuisine. We recommend the following accommodations for your post-trip hotel:

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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