Trek Travel Tuscany Explorer Bike Tour
Ride along vineyards on a Tuscany bike tour
Poppy flower fields on our Tuscany, Italy luxury bike tours
Stay at Borgo di Vescine on Trek Travel's Tuscany Explorer Bike Tour
Rolling hills on our Tuscany, Italy luxury bike tours
The freshest of ingredients on our Tuscany, Italy luxury bike tours
Old world buildings on our Tuscany, Italy luxury bike tours
Where will the road take you on our Tuscany, Italy luxury bike tours
Trek Travel Tuscany bike tour and cycling vacation
Trek Travel Tuscany Explorer Bike Tour Ride along vineyards on a Tuscany bike tour Poppy flower fields on our Tuscany, Italy luxury bike tours Stay at Borgo di Vescine on Trek Travel's Tuscany Explorer Bike Tour Rolling hills on our Tuscany, Italy luxury bike tours The freshest of ingredients on our Tuscany, Italy luxury bike tours Old world buildings on our Tuscany, Italy luxury bike tours Where will the road take you on our Tuscany, Italy luxury bike tours Trek Travel Tuscany bike tour and cycling vacation

Tuscany Bike Tour

Pedal La Bella Toscana: Chianti to the Val d'Orcia

On a Trek Travel Tuscany bike tour, surrender your senses to the “allegria” of Italy. Soak in the rich sights and smells of the endless vineyards from the saddle of your bicycle. The quiet, rolling roads of the Tuscan countryside offer gorgeous terrain that's a joy to pedal for cycling experts and novices alike. Sample a Chianti Classico in Radda and perfect your “cucina Italiana” at a private pizza-making class. Discover the breathtaking scenery of the Val d’Orcia and the walled town of Montalcino, the birthplace of the revered Montalcino red wines. The seductive, relaxed pace of "la dolce vita" is nowhere more evident than it is during our Tuscany bike tour—you're sure to fall under its spell on this cycling trip of a lifetime. Book your trip with confidence »
See the self-guided version of this trip »

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$3799 Per Person
6 Days & 5 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Hotel Level: ?
From $3799 per person View All Details
Trip Wows
Ride along quiet roads lined with cypress trees in the beautiful Tuscan landscape
Take part in an exclusive, private pizza making class using an original wood oven taught by an Italian pizza chef
Explore the traditional Tuscan flavors of extra virgin olive oil and Chianti Classico
Discover the walled medieval town of Montalcino and sample its revered red wine - Brunello di Montalcino
Stay in a 13th-century village that has been transformed into a charming and elegant hotel
Tuscany Bike Tour
This trip was better than anticipated and I had high expectations based on previous participants' reviews! I am now convinced that this is THE way to see a new country and experience its culture; by the sights, sounds, and smells only obtainable by cycling through its countryside. The support of the Trek guides made it exceptionally easy and enjoyable. A perfect way to spend our 15-year wedding anniversary! We'll be back!
-Kathy, Trek Travel Guest

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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Apr 17 – Apr 22 
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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.

Welcome to your Tuscany cycling trip! A one-hour shuttle will deliver you to your starting point for today's ride, a countryside trattoria set among the rich vineyards of Chianti. After a delicious lunch of handmade pizza and salads, your Trek Travel guides will ensure that you have an excellent fit to your Trek bicycle while offering specific cycling tips for riding in Italy. You’ll then start with a rolling, scenic loop ride among the vine-covered slopes and olive groves of the Chianti region. This evening, you and your companions will gather for an Italian aperitif on the hotel terrace as our chef prepares seasonal delights for tonight’s Tuscan feast.

Today's Ride:

Hotel Il Colombaio to Vescine
Approximately 16 mi | 25 km and 1,900 ft | 579 m


Il Borgo di Vescine

Included Meals:

Lunch | Social Hour | Dinner

Don’t forget your camera today as you descend into the valley where vines and olive trees give way to shady chestnut trees as the landscape subtly shifts and changes. Stop to visit the Castello di Brolio and its famous L’Eroica caffè, home to great espresso and cool cycling memorabilia. For lunch we'll stop at Bar Dante in Radda in Chianti. Our hosts, Fabrizio and Carolyn pride themselves on serving the best bruschetta in Radda, washed down with a glass of local Chianti. Following lunch, continue your ride to the tiny village of Lucarelli and join the locals for the ritual of mid-afternoon espresso. Alternatively, choose to wander the tiny streets of Radda. Buy a local bike jersey or some delicious Tuscan olive oil before shuttling back to the hotel to relax and enjoy the pool. This evening is yours to explore Castellina in Chianti; wander the medieval cobblestone streets before discovering the “Via della Volte,” an impressive, historic, underground tunnel that is now a fascinating walkway filled with artisan boutiques and restaurants. Enjoy a family-style dinner in town on the piazza, or perhaps something a little more romantic, while savoring the picturesque views and unique atmosphere of this charming village.

Today's Ride:

Vescine to Radda in Chianti Loop
Approximately 32 mi | 51 km and 2,800 ft | 853 m

Short Option:

Vescine to Radda in Chianti
Approximately 22 mi | 35 km and 2,000 ft | 609 m

Avid Option:

Vescine to Radda in Chianti with San Donato Loop
Approximately 49 mi | 78 km and 4,500 ft | 1,371 m


Il Borgo di Vescine

Included Meals:

Breakfast | Lunch

Following your morning cappuccino, get ready to enjoy stunning views of Siena’s towers amid the vine-covered hills on the route today. Surrounded by ancient stone walls, wildflowers, and the scent and shade of the forest, you leave the 21st century far behind. Pause a while to take in the sight of your mid-day destination, the walled town of Monteriggioni, perched on a hilltop and dominated by 14 dramatic towers. For lunch, take your pick of the many al fresco options lining the piazza, before embarking on an exploration of this enchanting city. Shuttle back to the hotel from here, or continue riding through some of the leading wine-growing districts in Chianti. This evening, join your fellow travelers for a fun-filled pizza making session at the hotel. You will learn how to prepare a perfect Italian pizza, paired, of course, with the region's local wines. Under the guidance of an Italian pizza master, you'll use the original wood oven of the hotel, still functioning since the times when the hotel was itself a small village.

Today's Ride:

Vescine to Monterggioni
Approximately 36 mi | 57 km and 2,400 ft | 731 m

Short Option:

Vescine to Santa Colomba with shuttle
Approximately 26 mil | 41 km and 2,000 ft | 609 m

Avid Option:

Vescine to Monterggioni Loop
Approximately 49 mi | 78 km and 4,500 ft | 1,371 m


Il Borgo di Vescine

Included Meals:

Breakfast | Dinner

Today you’ll head north into one of Italy’s most dramatic regions, the Crete Senesi, following winding ribbons of road into southern Tuscany’s gently undulating terrain. The hills, distinguished by the dramatic colors of the soil and blessed with some of the most stunning views in Tuscany, are sure to take your breath away. Nestled in the heart of the Val d’Orcia is the tiny town of Montisi and our favorite restaurant of the region, Taverna da Roberto. Here you will relax and enjoy a delicious farm to table lunch prepared by our friend and local chef Roberto, who is both passionate and faithful to the traditions of the slow food movement. Choose to either jump in the van or return to your bike and ride along cypress-lined ridges to this afternoon’s destination, the medieval village of San Quirico d’Orcia and our boutique hotel, the Palazzo del Capitano. The evening is yours to explore the cobbled streets of the town and to enjoy dinner at one of the many small bistros on your own.

Today's Ride:

Vescine to Montisi with shuttle
Approximately 45 mi | 72 km and 3,600 ft | 1,097 m

Short Option:

Vescine to Arbia with shuttle
Approximately 29 mi | 46 km and 2,600 ft | 792 m

Avid Option:

Vescine to San Quirico
Approximately 58 mi | 93 km and 5,050 ft | 1,539 m


Hotel Palazzo del Capitano Wellness and Relais

Included Meals:

Breakfast | Lunch

This morning’s route lifts you high above the Val d’Orcia, a vista dotted with rolling hills blanketed with vines and rows of cypress. Your first stop is a tiny Roman spa town of Bagno Vignoni, known for its hot sulfurous springs. The town plaza is filled with a pool built by the Medici family centuries ago, where you can refresh your feet before you continue on your ride to Abbazia di Sant’Antimo, a stunning 12th-century Romanesque abbey. If you're lucky, you may arrive to the choral harmonies of the monks' Gregorian chants—magical! Our lunch destination today is the walled village of Montalcino, whose 14th-century fortress and steep cobblestone streets dominate the surrounding countryside. Here you'll discover the delights of Brunello wine, one of the finest Italian varietals together with lunch at a local trattoria. Cycle back along winding roads or reward yourself with a shuttle and more time to relax back at the hotel. This evening, you will experience an exceptional dinner at our favorite restaurant in the heart of San Quirico. Enjoy a selection of traditional dishes with a modern twist, paired with a unique selection of regional wines. We will toast to a week of great riding, warm fellowship, and truly phenomenal food!

Today's Ride:

San Quirico to Montalcino Loop
Approximately 34 mi | 54 km and 3,100 ft | 944 m

Short Option:

San Quirico to Montalcino with shuttle
Approximately 23 mi | 37 km and 2,100 ft | 640 m

Avid Option:

San Quirico to Montalcino with Pienza Loop
Approximately 52 mi | 83 km and 5,200 ft | 1,584 m


Hotel Palazzo del Capitano Wellness and Relais

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

It’s sadly time to bid farewell today as your Tuscany cycling trip comes to a close. Get up bright and early this morning to make the most of the stunning light and watch a bright new day unfurl over the classic Tuscan countryside. Or linger awhile over a hot cappuccino and enjoy a more leisurely paced morning in the hotel. However you say goodbye to Tuscany, you’re sure to take a little of this destination with you.

Today's Ride:

San Quirico to Bagno Vignoni Loop
Approximately 17 mi | 27 km and 1,200 ft | 365 m

Included Meals:



hotel image

Il Borgo di Vèscine

Chianti, Italy

Explorer Accommodation | Il Borgo di Vèscine is a XIII century Etruscan village which has been transformed into a charming and elegant hotel. The rooms have been lovingly created within the original houses of the medieval hamlet. Situated in the heart of the Chianti region, this hotel boasts its own wine cellar and restaurant that offers guests the finest Chianti Classico Riserva wines accompanied by typical “Chiantigiana” cuisine.
hotel image

Hotel Palazzo del Capitano Wellness and Relais

San Quirico d'Orcia, Italy

Explorer Accommodation | This historic 15th-century palazzo is nestled in the heart of the charming village of San Quirico d'Orcia, and boasts its own traditional trattoria - Al Vecchio Forno, an indulgent YON-KA SPA and tranquil gardens with two pools. Its mix of modern details and rich history is sure to enchant you.

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 Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019, we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More


Trek Electric-Assist Domane+ LT

The Domane+ LT combines the best of the race-built Domane endurance bike with a slight pedal-assist perfect for climbing the toughest hills. This bike primarily functions as a road bike, but on tough hills or in strong headwinds, you can get an extra boost by using the electric assist feature. Upgrade to the Domane+ LT on this trip for $500. Learn More


Trek Electric-Assist Verve+

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. Learn More


  • Five nights of accommodation at handpicked 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 Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag 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 pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals)
  • Bontrager WaveCel helmets
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your Tuscany cycling trip
  • A personalized digital photobook of your trip
  • Entrance fees for all activities, private tours and events


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Upgrade your bike to a Trek Electric-Assist Domane+ LT carbon road bike with Shimano Di2 electronic shifting
  • Trek Travel Bontrager cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Upgrade your bike to include carbon wheels (+$200, subject to availability)
  • 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 trip, we recommend $240-$300 per guest. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or Venmo 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?

48 kilometers / 30 miles
383 kilometers / 238 miles
792 meters / 2,600 feet
6,620 meters / 21,750 feet
On our Tuscany bike tour, the terrain is hilly, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of five kilometers long. Tuscany biking is best suited for our Type 3 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option—you still get a workout but can climb alongside even the strongest rider. Type 4+ Riders will enjoy the extra mileage the avid route options offer.
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 bike tour are:
  • Explore the walled city of Castellina
  • Shop and explore the medieval villages of Radda, Lecchi, Montalcino, Pienza and San Quirico
  • Take a side trip to Siena
  • Enjoy an Italian pizza making class
  • Opt to spend a half day at a local spa
  • Wine and cheese taste in Radda, Pienza or Montalcino

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. 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)
11:00 AM
Hotel Montebello Splendid, Florence, Italy

Say Farewell

Florence Airport (FLR)
12:30 PM
Hotel Montebello Splendid, 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 (~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 ~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 at the Hotel Montebello Splendid (Via Giuseppe Garibaldi, 14, 50123 Florence, Italy) at 11:00 AM on the first day of the trip. Should you wish to reserve a room at this hotel pre-or post-trip, please contact your Trip Consultant for a discount code. 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 Domane 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, Il Borgo di Vescine (+39 0577 741 144) and leave a message with your expected arrival time and contact details. You may take a taxi to the first night’s hotel in Vescine, Il Borgo di Vescine, for approximately 200 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 the Villa del Capitano, San Quirico. You’ll depart by private shuttle for Hotel Montebello Splendid, Florence, arriving at around 12:30 PM. The hotel is a 10-minute taxi 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. for train information.

For all guests returning to the United States, COVID-19 testing can be booked at the end of the trip at a convenient location that allows for proper timing to receive results. Your guides can provide more information on the first day, should you require a test during your trip with us. See our Travel to Europe page for updated information on the latest US re-entry requirements.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Spring and fall in Tuscany are usually clear and sunny, with warm daytime temperatures (75F-90F) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Summers are warmer with warm daytime temperatures (80F-95F). Rain is always a possibility, however, so be prepared with wet-weather gear 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:

Customer Reviews

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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