| Months |
April, May, June, August, September, October | View Dates» |
| Price (USD) |
From $2,499 | See Pricing» |
| Start & End |
Florence, Italy |
| Trip Length |
6 days | 5 nights |
| Rider Type |
3 | Learn More» |
| Daily Rides |
Options from 15 - 50 miles |
| Beyond Biking |
Historical Site Visit, Cultural Tour, Wine Tasting, Food tasting, Spa, Shopping |
| Trip Options |
Make it Private or Choose Your Own Date |
 |
Bid farmers "Buongiorno!" from the seat of your Trek bike as you tour the roads of Tuscany. 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–you’re sure to fall under its spell on this cycling vacation of a lifetime.
Trip Wow’s
- Step back in time with a private guided walking tour through the village of Volterra to discover its ancient Etruscan and Roman roots.
- Enjoy a sumptuous picnic lunch at Villa di Filicaja as well as a tasting of our good friend Antonio’s locally produced wine and olive oil. Spend time with your host and learn more about how he came to run Italy’s largest horse rescue shelter.
- Stay in our best kept secret, the incredibly beautiful town of Volterra, a hidden gem away from any tourists.
Days 1 – 3 | Castellina in Chianti
Stay at Palazzo Squarcialupi
Cycle through the rolling hills of the Chianti countryside | Discover the local wines of Chianti during our private wine tasting | Visit Radda in Chianti, the capital of the Ancient League of Chianti | Visit art galleries, shop artisan’s stalls, and discover hidden walkways exploring the walled towns of Castellina in Chianti and Monteriggioni
Days 4 – 6 | Volterra
Stay at Palazzo Squarcialupi
Challenge yourself on rides to hilltop towns and enjoy the small winding roads through the Tuscan hills | Learn about Volterra's rich history with an evening walking tour with your local guide
Palazzo Squarcialupi | Chianti, Italy
Located in the heart of Castellina in Chianti, a medieval city and one of central Tuscany's most charming villages. The hotel, a 14th century palace, boasts a remarkable view of the stunning Chianti hillsides and comfortable rooms that highlight the hotel's original structure.
Park Hotel Le Fonti | Volterra, Italy
Recently renovated, the Park Hotel Le Fonti is designed according to old Tuscan traditions, while at the same time offering all the comforts of a top modern hotel. The view of the surrounding hills from the swimming pool and terrace are unbeatable!
What’s Included in the Trip Price
- 5 nights of accommodation
- Daily breakfast, 1 lunches, 1 social hours, 3 dinners, and all snacks and drinks for each day
- The knowledge, support, and camaraderie of experienced guides
- Daily route support
- The use of a Trek Domane™ 5.9 carbon road bike, or Trek Domane™ 5.9 Women’s Specific Design carbon road bike (limited selection), or Trek 7.6 FX™ hybrid bike
- The use of Trek bike helmets and other gear and equipment to make your ride comfortable
- Trek Travel water bottles
- Private tours
- Entrance fees to all group events/activities
- All luggage transfers
- All transportation during the trip, including private coaches
- Comprehensive trip literature and complimentary Trek merchandise
- All gratuities for special events, local guides, transfers, hotels, and restaurants
- $300 Discount on a 5 or 6 series Trek Domane or Madone, or Project One purchased at your local Trek retailer
Not Included
- Airfare to and from the trip
- Transportation to the trip pick-up location
- Lodging before and after the trip
- Gratuities for Trek Travel guides
- Personal items purchased during the trip
- Some meals are not included in each destination, which allows you the opportunity to explore regional cuisine on your own. Your guides are happy to make recommendations should you so desire.
What is the weather going to be like?
Fall in Tuscany is 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. Rain is always a possibility, however, so be prepared with wet-weather gear in order to best enjoy your vacation.
What are the daily rides like?
| Rider Type | 3 |
Average Daily Mileage | 40 |
| Terrain | hilly |
Average Daily Elevation | 2,100 |
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. 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. 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. See Itinerary for specific daily ride distance and elevation options.
What are the options for a non-rider travel companion?
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. See Included In The Trip Price for more information.
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
- 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
General FAQs
Didn’t find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don’t necessarily pertain to a specific trip.
| Trip | Dates | Price (USD) |
| Tuscany 2013Value Series |
May 12-17, 2013 |
Limited Availability |
$2,499 per person | $850 single occ. |
| Value Series |
May 19-24, 2013
|
Limited Availability |
$2,499 per person | $850 single occ. |
| Value Series |
Jun 2-7, 2013 |
Sold Out
|
$2,499 per person | $850 single occ. |
| Value Series |
Jun 16-21, 2013 |
Limited Availability |
$2,499 per person | $850 single occ. |
| Value Series |
Jun 23-28, 2013 |
Guaranteed Date* |
$2,499 per person | $850 single occ. |
|
Sep 8-13, 2013 |
Guaranteed Date* |
$3,299 per person | $850 single occ. |
|
Sep 15-20, 2013 |
Guaranteed Date* |
$3,299 per person | $850 single occ. |
|
Sep 22-27, 2013 |
Guaranteed Date* |
$3,299 per person | $850 single occ. |
|
Sep 29-Oct 4, 2013 |
Guaranteed Date* |
$3,299 per person | $850 single occ. |
|
Oct 6-11, 2013 |
Guaranteed Date* |
$3,299 per person | $850 single occ. |
| Tuscany 2014Value Series |
Apr 20-25, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
Apr 27-May 2, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
May 4-9, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
May 18-23, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
Jun 15-20, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
Jun 22-27, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
Jun 29-Jul 4, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
Jul 27-Aug 1, 2014 |
|
$2,499 per person | $850 single occ. |
| Value Series |
Aug 3-8, ,2014 |
|
$2,499 per person | $850 single occ. |
|
Sep 7-12, 2014 |
|
Coming soon |
Note: Value Series are the same trip but at a seasonal rate thanks to our relationship with our hotel partners.
Want to travel with your with friends, family, or colleagues? We can make any trip private. More»
Our dates don't fit your schedule? Use Travel Match and suggest your own date. More»
*Our 2013 trips are guaranteed to run once we have one confirmed booking on the trip. Trek Travel reserves the right to cancel trips with zero guests, therefore you must book with Trek Travel before making travel arrangments for the trip. We are not responsible for travel arrangements made prior to confirming your Trek Travel Trip. Guaranteed trips do not include Cross Country, Santa Barbara to Taos, Pyrenees Sea to Sea, or any Race trips.
Wow’s From Our Guests & More Photos
When we asked our guests what their favorite WOW's were from their Tuscany bike vacations, here is what they said…
The designs for the rides were a perfect mix linking all of the important points of interest with the countryside of Tuscany. The camaraderie and challenge all combine to create a close-knit group of newly found friends—Tom
All of Tuscany was beautiful - Diane and Nate provided incredible service/assistance when needed. Always cheerfully and with professionalism. It was truly a trip of a lifetime! We have many pictures and happy memories.—Carol
I had a fantastic time on my first Trek Travel vacation! Nate and Diane contributed to my wonderful experience, and the other guests on the trip were all very nice. We had good chemistry and I think everyone on this trip had a great time! Hope to see everyone in Lake Cuomo (hint, hint)!—Maria
The bike! I had the Madone 5.5 and it was great. The guides! Very supportive of whatever we wanted. The scenery! First trip to Tuscany and it was fun!—Bruce
This was our first cycling trip and it definitely exceeded our expectations!—Katharine
