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Tuscany Explorer

Pedal La Bella Toscana: Chianti to San Gimignano

Surrender your senses to the “allegria” of Tuscany from the saddle of your bike. Awash in the rich sights and smells of the endless vineyards, 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, or stop in the walled town of Monteriggioni to enjoy a delicious white truffle. Discover the remains of Etruscan life and the spectacular Roman ruins in the hilltop town of Volterra. The seductive, relaxed pace of "la dolce vita" is nowhere more evident than it is here—you're sure to fall under its spell on this cycling vacation of a lifetime.

Trek Travel Bike Tour Luxury Upgrade Icon Upgrade to Tuscany Luxury

$3899 Per Person
6 Days & 5 Nights
Rider Type: ?
3 - Active Non-riders Welcome
Hotel Style: ?
Bike Included:
Trek Domane SL 7 More options available
From $3899 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 cooking class at a local winery and olive oil farm where you’ll create your own Tuscan feast under the guidance of an Italian master of the kitchen
Explore the traditional Tuscany flavors of extra virgin olive oil and Chianti Classico at our exclusive wine tasting
Discover Volterra’s ancient living Etruscan and Roman heritage on a walking trip guided by a local expert
Stay in a 13th century Etruscan village which has been transformed into a charming and elegant hotel
Watch the Experience
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!

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 and date are guaranteed.
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Single Occupancy from: +$650
Jun 3  – Jun  8
Sold Out
$3899 / Person, Double Occupancy Add to waitlist
Jun 10  – Jun  15
Guaranteed Limited Availability
$3899 / Person, Double Occupancy Book this date
Jun 17  – Jun  22
Guaranteed Limited Availability
$3899 / Person, Double Occupancy Book this date
Jun 24  – Jun  29
Guaranteed Limited Availability
$3899 / Person, Double Occupancy Book this date
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. All you need to do is pick any open 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 +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
*Pricing, availability and guest minimums are all subject to change at any time. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
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. We’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:

La Cantoniera to Vescine
Approximately 19 miles with 1,900 feet of climbing


Il Borgo di Vescine

Included Meals:

Lunch | Social Hour | Dinner

This morning, you'll climb high up above the vineyards, where you'll be rewarded by rich panoramic views of rolling Tuscan hills discreetly chaperoned by the ubiquitous cypress. As you gently descend you'll cruise through tiny medieval hamlets and into the shadow of the grand Castello di Brolio. 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 which 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 miles with 2,800 feet of climbing

Short Option:

Vescine to Radda in Chianti
Approximately 22 miles with 2,000 feet of climbing

Avid Option:

Vescine to Radda in Chianti with San Donato Loop
Approximately 49 miles with 4,500 feet of climbing


Il Borgo di Vescine

Included Meals:

Breakfast | Lunch

Don’t forget your camera today as you descend into the valley, enjoying stunning views of Siena’s towers amid the vine-covered hills. As you ride, vines and olive trees give way to shady chestnut trees as the landscape subtly shifts and changes. 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 alternatively continue riding through some of the leading wine-growing districts in Chianti. This evening, join your fellow travelers for a private wine tasting where you’ll taste the famous Chianti Classico wines of the region. Finally, it's on to enjoy another sumptuous dinner and more Tuscan hospitality before a well-deserved nights rest.
Today's Ride:

Vescine to Monteriggioni
Approximately 36 miles with 2,400 feet of climbing

Short Option:

Vescine to Strove with shuttle
Approximately 30 miles with 2,100 feet of climbing

Avid Option:

Vescine to Monteriggioni Loop
Approximately 49 miles with 4,000 feet of climbing


Il Borgo di Vescine

Included Meals:

Breakfast | Social Hour | Dinner

The breathtaking Elsa Valley, or Val d’ Elsa awaits you today. The quiet roads offer rich, colorful vistas of golden hills dappled with silver grey olive groves and framed by the dark green cypress. After this beautiful morning ride, you’ll enjoy a stop for lunch in the ancient town of Certaldo. Originally an Etruscan settlement turned medieval walled city, then Medici era stronghold the old town sits atop a plateau commanding magnificent views of the surrounding countryside. Walk or take the funicular up to wander through the beautiful brick old town and admire the 12th century frescos. Here you’ll enjoy an organic picnic lunch at an Osteria in the medieval center of town, full of shady terraces with the soft tunes of jazz floating their way through the tranquil old streets. Later, ride up to the stunning medieval town of San Gimignano or shuttle back for a refreshing dip in the outdoor swimming pool. This evening you are free to wander in the myriad of cobbled streets to shop for some souvenirs or taste a new Tuscan wine before dinner at your choice of many delicious trattorias in San Gimignano.
Today's Ride:

Vescine to Certaldo to Collegiata
Approximately 32 miles with 2,600 feet of climbing

Short Option:

Vescine to Certaldo w/shuttle to hotel
Approximately 24 miles with 1,600 feet of climbing

Avid Option:

Vescine to Certaldo to Collegiata with Ulignano Climb
Approximately 45 miles with 4,000 feet of climbing


Hotel La Collegiata

Included Meals:

Breakfast | Lunch

You will begin with a climb up through the famous Vernaccia di San Gimignano vineyards before gliding down to the valley below as the magnificent medieval town of Volterra comes into view. This historic town with Etruscan roots and Roman influences has many secrets to discover on its winding, cobbled streets. Have lunch at a cafe of your choosing before a historical walking tour guided by a local expert, to learn about the origins of this fascinating town dating back before the 7th century BC. This afternoon, choose to return to the hotel to relax or ride back through the breath taking Tuscan countryside. This evening, you are off to a private cooking class at a local family winery and olive-oil producing farm, where you’ll create your own Tuscan masterpiece under the guidance of a local Italian chef. We will toast to a week of great riding, warm fellowship, and truly phenomenal food!
Today's Ride:

San Gimignano to Volterra Loop
Approximately 40 miles with 4,000 feet of climbing

Short Option:

San Gimignano to Volterra
Approximately 19 miles with 2,400 feet of climbing

Today’s activity:

Learn the secrets of "Cucina Italiana" at a private cooking class


Hotel La Collegiata

Included Meals:

Breakfast | Social Hour | Dinner

It’s sadly time to bid farewell today. 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 Gimignano to San Benedetto Loop
Approximately 12 miles with 1,300 feet of climbing

Included Meals:



hotel image

Il Borgo di Vèscine 

Chianti, Italy

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 La Collegiata

San Gimignano, Italy

Originally a 15th century monastery, this luxurious 4 star hotel treasures its ancient Tuscan traditions, while at the same time offering all the comforts of a top modern hotel. Relax by the pool and enjoy a cocktail on the terrace or stroll into the medieval town of San Gimignano.

Travel Details

How to Get There

Florence’s AmerigoVespucci Airport (FLR)
11:00 AM
Home Hotel Florence, Florence, Italy

Say Farewell

Florence’s AmerigoVespucci Airport (FLR)
12:30 PM
Hotel Palazzo Vecchio, Florence, Italy


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 AmerigoVespucci Airport (FLR).The Florence airport is about 3 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 1.5 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 Home Hotel Florence (Piazza Piave, 3 - 50122 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 start 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 Hotel La Collegiata, San Gimignano. You’ll depart by private shuttle for Hotel Palazzo Vecchio, 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 2:00 PM. The airport in Florence (FLR) is 3 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

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip 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

Trek’s latest innovation has led to the best bike on the road—a light weight, stable and technologically advanced machine to make even the hardest roads seem easy. Ride confidently, comfortably and longer in the most beautiful destinations around the world. Upgrade your bike with carbon wheels for only $200. Learn More


Trek Electric-Assist XM700+

It’s lightweight and equipped with an adjustable pedal-assist motor that helps riders of all skill levels stay together, play together and make some great memories together. Included at no additional cost, these bikes will be available on a first-come, first-served basis, so reserve yours when you book today. Learn More

Trek 7.6 FX Hybrid

Trek 7.6 FX Hybrid
is also available on this trip


  • 5 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, 3 lunches and 3 dinners
  • Social hour of drinks and hors d’oeuvres on your first and last night of the trip
  • Ride a Trek Domane SL 7, Trek’s newest Electric-Assist, or a Trek 7.6 FX Hybrid
  • Three daily route options
  • Snacks and drinks for each day’s ride
  • Trek Travel Bontrager RL cycling jersey
  • Trek Travel water bottles to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, front and rear Bontrager Flare R lights, a Bontrager saddle and pedals of your choice
  • All gratuities for drivers, local experts and hospitality staff
  • All luggage transfers and transportation during your trip
  • A personalized photobook of your trip
  • Entrance fees for all activities, private tours and events


  • Trek Domane SL 7 carbon road bike with Shimano Di2 electronic shifting or Trek 7.6 FX Hybrid bike to use
  • Trek Electric Assist XM700+ also available in a limited quantity to use
  • Trek Travel Bontrager RL cycling jersey
  • Trek Travel water bottles
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals
  • Bontrager helmet and saddle to use
  • Bontrager front and rear Flare R lights
  • Flat pack
  • Upgrade your bike to include carbon wheels (+$200)
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • You may bring your own pedals and saddle on the trip. Your guides will install your gear on the first day during your bike fit.


Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the 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?

29 miles
171 miles
2,500 feet
15,000 feet
The terrain is consistently rolling, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of 5km long. Tuscany 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 on this trip are:
  • Explore the walled city of Castellina
  • Shop and explore the medieval villages of Radda, Lecchi, Montaione, Monteriggioni and San Gimignano
  • Take a side trip to Siena
  • Enjoy an Italian cooking class
  • Discover why Tuscan wines and olive oils are so renowned during our private wine-tasting
  • Opt to spend a half day at a local spa
  • Visit the museums of Volterra

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel strives 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.

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 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 all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

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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