You've found the sweet spot. It's in that classic tableau of vineyard-draped hillsides and medieval villages. It's on your table, tucked between the earthy flavors of pappardelle al cinghiale and the rich aroma of local porcini and tartufo nero. It's in your glass - because you just discovered that a superb Chianti Classico tastes even better after a day of biking from one village to the next. It's all around you, in the welcoming smiles of our local Tuscan friends, chefs and winemakers. This is how vacations were meant to be. Sweet indeed.
Days 1-2 Climb the ridges and cruise the downhills in the beautiful Val di Chiana Kick off the week in true Tuscan style with a grigliata mista under the stars Flex your cycling muscles on a ride through the Val d'Orcia's rolling hills Explore the Renaissance gem of Pienza, pausing to taste pecorino cheese and southern Tuscan wines Prepare a traditional meal, from l'antipasto to i dolci.
Day 3 An exclusive wine tasting at Fèlsina estate, one of the finest producers of Chianti Classico View the bare chalk hills rising above woods and vineyards as you approach quintessential Chianti Stroll through grand piazze and alleyways, soaking up the medieval charm of Siena Treat yourself to a slice of Sienese panforte and local vin santo.
Day 4 Pedal through oak-shaded valleys and castle-crowned hills, watching the landscape alternate between perfectly symmetrical vineyards, gnarled olive trees and ancient forests Admire hand-painted pottery at Ceramiche Rampini, then explore the shops and markets of Radda in Chianti At a private olive oil tasting, learn why Tuscany's "liquid gold" is beloved around the world Create a four-course Tuscan spread in a local kitchen.
Days 5-6 World-famous Chianti vineyards provide a stunning backdrop for our ride Relax over a cappuccino in lively Castellina While your handmade pizza bubbles in the wood-fired oven, gaze across the valley to the villa where Mona Lisa once lived Visit the famed butcher shop of Dario Cecchini, who stocks specially prepared salts and medieval seasonings Enjoy a traditional osteria experience at Il Papavero, where our friends introduce you to classic Tuscan dishes with an elegant twist Treat yourself to a morning spin before returning to Florence.
- Return from your trip with actual know-how to create a Tuscan dinner for your famiglia back home - it's the ultimate keepsake!
- Journey into the heart of Chianti - and back in time - to sensational Siena and Radda
- Shadow the hilly course of L'Eroica, Tuscany's internationally recognized vintage bike race
- In ancient cellars, taste superb Tuscan wines, from Chianti Classico to Vino Nobile di Montepulciano
- Overnight in distinctive hotels where you're welcomed like family
Borgo Casabianca (2 nights): An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool, tennis)
Villa Curina Resort (1 night): A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool, tennis)
Hotel San Niccolo (2 nights): This refurbished manor house enjoys an enviable location amid the many shops in the heart of town. (pool)
Every Backroads trip is designed to appeal to a wide variety of
interests and fitness levels. We know your pace may vary from one
day to the next-and your traveling companion's may differ somewhat
from yours. So we present a range of mileage options, and each
day you decide exactly what and how much you want to do.
Routes For All Abilities
|Daily Route Options|
|Level 1||Level 2||Level 3||Level 4||Level 5|
|miles||feet gain||miles||feet gain||miles||feet gain||miles||feet gain||miles||feet gain|
|Casabianca Cooking Class (2.5 Hours)|
|Chianti Classico Wine Tasting (45 Minutes)|
|Educational Olive Oil Tasting (30 Minutes)|
|Radda Cooking Class (2 Hours)|
|Pizza Making and Lunch (2 Hours)|
* Includes a shuttle
2015 Dates & Pricing*
- 5/3-8 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 5/17-22 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 5/31-6/5 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 6/14-19 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 6/28-7/3 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 7/5-10 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 8/30-9/4 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 9/6-11 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 9/13-18 Price: $4098 pp dbl. occ., (+ $790 for sgl. occ.)
- 9/20-25 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 9/27-10/2 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
- 10/4-9 Price: $3898 pp dbl. occ., (+ $790 for sgl. occ.)
*Prices may change. Once you book your trip, your price is guaranteed.
Private Trips Options & Pricing
Gather your favorite people to share a Backroads adventure on a ready-to-book Private Trip - featuring all the legendary Backroads hallmarks from expert leaders to unforgettable activities.
You can pick from a large selection of dates for your group of 8 or more. Call us for date availability.
If your party has fewer than 8 guests, or if your preferred date is not available, we'll create a departure just for you.
Pricing for Private Trips (prices may vary based on departure date)
|2 - 3 guests from $5,898 pp dbl. occ.||8 - 9 guests from $4,598 pp dbl. occ.|
|4 - 5 guests from $5,198 pp dbl. occ.||10 - 11 guests from $4,198 pp dbl. occ.|
|6 - 7 guests from $4,798 pp dbl. occ.||12 or more guests from $3,898 pp dbl. occ.|
All Private Singles-Solos trips require a minimum of 16 guests.
Guest Trip Reviews
This trip brings you the full taste of Tuscany, including world-famous wines, cheeses, grilled meats, pasta and pizza. Every day you'll enjoy several special culinary-focused activities, plus opportunities for exploring, shopping and interacting with local people. We visit the two most beautiful areas of the region - the Val d'Orcia and Chianti - passing through countless small villages along the way. Though the daily biking mileage on this trip is shorter than on our other Tuscany trips, be prepared for lots of uphills and downhills on winding country roads!- Regional Manager, Italy