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Tuscany Active Gourmet Bike Tour New!

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Trip Highlights
  • 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

Call 800-462-2848, Every day 6am-6pm,PST

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Chianti's History, Hills & Hearty Flavors

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.

Casual Inns

Accommodations may vary based on departure date. Any difference from what is listed below can be found by clicking on your desired date on the Dates & Prices tab.

Borgo Casabianca
Borgo Casabianca

Asciano (2 nights) An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool, tennis)

Villa Curina Resort
Villa Curina Resort

Curina (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
Hotel San Niccolo

Radda in Chianti (2 nights) This refurbished manor house enjoys an enviable location amid the many shops in the heart of town. (pool)

Guest Reviews About This Trip

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!
Jeff Cantarutti- Regional Manager, Italy

Trip Dates & Prices

Please click on a date below for specific pricing and possible itinerary variations.

2015 August
2015 September
2015 October
2016 May
2016 June
2016 July
2016 August
2016 September
2016 October

Don't see your ideal travel date? Call us at 800-462-2848 for Private Trip date availability.

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This Trip Is Rated Level 1-4

Routes For All Abilities
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.

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
1 24 2200
2 22* 1100 45 2200
Casabianca Cooking Class (2.5 Hours)
3 27* 2200
31 2400
36 2800
Chianti Classico Wine Tasting (45 Minutes)
4 15* 1400 25 3000
22 1900
Educational Olive Oil Tasting (30 Minutes)
Radda Cooking Class (2 Hours)
5 19* 2000 27 2900
34 3000
Pizza Making and Lunch (2 Hours)
6 12 700

* Includes a shuttle

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.


2 - 3 guests from $5,998 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 $4,098 pp dbl. occ.
6 - 7 guests from $4,798 pp dbl. occ. 12 or more guests from $3,798 pp dbl. occ.

All Private Singles-Solos trips require a minimum of 16 guests.

For 36 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. See our award-winning Europe Italy biking tours, Europe Italy walking and hiking tours and Europe Italy multisport tours.


Casual Inns

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Route Rating

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Arezzo, Italy/Florence, Italy

Detailed Itinerary

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Trip Notes

All meals included except 1 dinner

Recommended Reads

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