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Tuscany Bike Tour

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Trip Highlights
  • A quintessential Tuscan experience from south to north
  • Sample fine wines before dining on local specialties
  • Relax at day's end in cozy historic hotels, all with swimming pools
  • Explore some of the region's most celebrated towns, including Pienza, Montalcino, Siena and Radda in Chianti
  • Pedal rolling hills past Brunello, Chianti Classico and Sangiovese vineyards

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

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A Taste of Tuscany from Pienza to Siena & Chianti

To D.H. Lawrence, Tuscany was "the perfect centre of man's universe." Poet Shelley called the region a "paradise for exiles." Dante, a Tuscan native, more than likely called it "divine." You'll undoubtedly conjure up a few superlatives of your own as you pedal from one unbelievable view to the next, gaze in awe at incredible Renaissance art and architecture, and savor delicious pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Few things in this world live up to the hype. We're delighted to report that everything you've ever heard about Tuscany is true.


Days 1-2 Explore some of the region's most celebrated towns, including Pienza, famous for pecorino cheese, exquisite ceramics and Renaissance architecture After savoring Tuscan treats, pedal cypress-lined roads through southern Tuscany's open undulating terrain into the Val d'Orcia   Montepulciano, with its winding streets and hidden squares, invites a stroll.

Day 3 Climb through a sea of vineyards to the wine village of Montalcino,  where enoteche pour samples and remarkable views reach as far as Siena on a clear day  Check out Abbazia di Monte Oliveto Maggiore, the region's most notable monastery, where monks still pray in Gregorian chant.

Day 4 Engaging Q&A session with Dario Castagno, author of Too Much Tuscan Sun  Bike past the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings  Sun-baked pastures dotted with sheep and crumbling stone farmhouses make way for oak woodland and olive groves Explore Siena on your own.

Days 5-6 Pedal rolling hills alongside Chianti Classico and Sangiovese vineyards  Get to know ridgetop Radda, the center of Chianti wine production, and Castellina, a medieval village with a unique arcaded passageway  Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.

Casual Inns

Albergo le Terme
Albergo le Terme

Bagno Vignoni (2 nights) This charming family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)

Borgo Casabianca
Borgo Casabianca

Asciano (1 night) 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 (2 nights) A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool, tennis)

Guest Reviews About This Trip

I can see how these trips can become addicting. This was the BEST way to experience Tuscany. You are encouraged to be in the moment, focusing only on the road in front of you, the beauty that surrounds you and the food you will indulge in when you reach your destination.
Lisa Weitzman- Westport, CT
Magnifico! I can't think of a better way to immerse myself in the Italian culture in the Tuscany region than with Backroads. The scenery, wonderful local towns/bastions, the food (off the charts), gracious people, the great leaders and people on the trip exceeded my expectations once again. We ate like kings (peasants technically), stayed in wonderful accommodations complete with their own great views, sampled the wine like royalty, the pizza and sorbet we gorged on were out of this world, and we biked some of the most beautiful countryside I have traveled. Time will tell where Backroads will lead me next...
Jeff Dalton- Annapolis, MD
This trip changed my life. I am a passionate biker, and this was the best week of my life. I will be a Backroads junky.
Terry Reed- Potsdam, NY

Trip Dates & Prices

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

2015 August
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2015 October
2016 April
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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 2-5

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 23 800
2 25* 1600 34 1700 44 2500 65 4300
3 26* 2500 42 3000
51 3900
4 26* 1200 33 1500 47 2300
5 24* 2000 38* 2600 53 3400 64 4800
6 13 700

* 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 $5,598 pp dbl. occ. 8 - 9 guests from $4,198 pp dbl. occ.
4 - 5 guests from $4,798 pp dbl. occ. 10 - 11 guests from $3,698 pp dbl. occ.
6 - 7 guests from $4,398 pp dbl. occ. 12 or more guests from $3,398 pp dbl. occ.


2 - 3 guests from $5,698 pp dbl. occ. 8 - 9 guests from $4,198 pp dbl. occ.
4 - 5 guests from $4,898 pp dbl. occ. 10 - 11 guests from $3,698 pp dbl. occ.
6 - 7 guests from $4,498 pp dbl. occ. 12 or more guests from $3,398 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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Florence, Italy

Detailed Itinerary

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Trip Notes

All meals included except 2 lunches, 1 dinner

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