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Tuscany Bike Tour

Route Rating
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Trip Highlights
  • Ride, relax and savor every drop of this vintage Backroads experience 
  • Pedal our favorite Tuscan roads with ample shuttle support
  • Luxuriate at handpicked hotels that represent Tuscany's finest
  • Taste critically acclaimed wines with a local sommelier
  • Discover idyllic hilltop towns brimming with medieval and Renaissance architecture

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

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Chianti to Montalcino, the Birthplace of Brunello

Few things in this world live up to the hype. But everything you've ever heard about Tuscany is true. It's not a destination. It's an experience. Routes lined with cypress trees overlooking the patchwork vineyards below will stop you on your bike. And no view will compare to that view. Until you round the next bend and see another. It's a wonder anyone ever finishes the rides. And that's only what you'll see; imagine the wines and flavors you'll discover.

Day 1 The quintessential Tuscan journey, offering the most scenic routes from Florence to Montalcino  Sample fresh cheeses at an agriturismo before biking serene roads past olive orchards, farmhouses and wheat fields  Pedal to medieval Greve and stroll through nearby Montefioralle, the home of Amerigo Vespucci, the Tuscan explorer who discovered New York Harbor.

Days 2-3 Ascend quiet roads into the heart of the Chianti region The hidden nooks of Via delle Volte, Castellina's unique arcaded passageway, are a delight to explore  Cruise the ridge to the ancient hilltop town of Radda, long the center of Chianti wine production Visit Badia a Coltibuono ("Abbey of the Good Harvest"), where you're treated to a private tour and olive oil tasting  Wine and dine in exclusive style - for one special evening, San Felice's renowned restaurant is open just for us.

Day 4 The narrow streets of Montalcino, known for harboring the region's finest wines, are yours to discover  Point your wheels toward southern Tuscany, where stately cypresses crisscross open rolling hills  Our route leads through the chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine paintings.

Days 5-6 Taste world-famous Brunello  Pedal through the undulating wheat fields and hilltop towns of the Val d'Orcia  In Pienza, marvel at extraordinary Renaissance architecture and sample splendid pecorino cheese.

Guests Reviews About This Trip

Beyond special...the indulgence of a consistent 5-star experience in locations only experienced in the movies.
Fredric Levin - Aspen, CO
We had a spectacular trip. I made the comment to my wife after the very first day of biking that I could go home today and feel like all my expectations had been fulfilled - and that was just the first day! Thanks, Backroads, for the trip of a lifetime!
Michael Kellum - Allen, TX
We had a fabulous time - our leaders were fantastic!! We loved the fact that support was always available and that we periodically saw the other group members on the road but for much of the time it was just the two of us enjoying the scenery and the ride. We can't wait to come back and do another Backroads trip. Meals were fantastic and we totally enjoyed the flexibility to ride as much or as little as we wanted. All in all it was definitely the best vacation ever - can't wait to download my 500+ pictures - everywhere was "una bella vista."
Michelle Ross - Atlanta, GA

Premiere Inns

Castello del Nero
Castello del Nero

Tavarnelle Val di Pesa (1 night) Situated on a hilltop overlooking rolling vineyards and olive orchards in the Colle Fiorentini, this former castle is steeped in Tuscan charm. (pool, spa)

Relais Borgo San Felice
Relais Borgo San Felice

San Felice (2 nights) Praised by the Hideaway Report as an "enchanting resort enclave set within a restored medieval hamlet fringed by olive groves and vineyards in the Chianti Classico region." A Relais & Châteaux member. (pool, spa, tennis)

Castello di Velona
Castello di Velona

Castelnuovo dell'Abate (2 nights) This 11th-century fortress features terra-cotta floors, individually decorated rooms and stunning views of the Val d'Orcia. A Small Luxury Hotels of the World member. (pool, spa)

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 $6,698 pp dbl. occ. 8 - 9 guests $5,298 pp dbl. occ.
4 - 5 guests $6,098 pp dbl. occ. 10 - 11 guests $4,698 pp dbl. occ.
6 - 7 guests $5,598 pp dbl. occ. 12 or more guests $4,398 pp dbl. occ.

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 22 1400
2 25* 1700 38* 2200 48 2900 55 3300
3 20* 1900 31 2500 38 3200 48 3900
4 28* 1200 33* 1200 49 2600 61 3500
5 22* 2000 32* 2400 45 3500 62 4700
6 14 900

* Includes a shuttle

For 35 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.


Premiere Inns

6 days, 5 nights
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Trip Price**
  • $4,398 to $4,898 pp dbl. occ.
  • (+$1,860 for sgl. occ.)

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arrow View Bike Options and Available Upgrades


Florence, Italy

Detailed Itinerary

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Dates & Prices

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2014 Classic Dates
Trip Notes

All meals included except 2 lunches, 1 dinner

Recommended Reads

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Cancellation Policy

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** Prices may change. Once you book your trip, your price is guaranteed.