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Tuscany Bike Tour

A Journey through Chianti

  • 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 like Castello del Nero, which houses a Michelin-starred restaurant
  • Taste Chianti and vernaccia, among other critically acclaimed regional wines
  • Discover idyllic hilltop towns brimming with medieval and Renaissance architecture

Tuscany is not a destination. It's a sublime experience. Cypress-lined roads overlooking the vineyards 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, flavors and luxuries you'll discover. 

Tuscany Italy Map


Day 1 Embark on the quintessential Tuscan journey, offering the most scenic routes from Florence to Siena  Sample Tuscan specialties at an agriturismo (working farm) before biking past olive orchards and vineyards  Easy pedaling along the sette ponti (seven bridges) road through well-kept villages leads us to our hotel for the night, Il Borro, a former village with an award-winning winery  Kick off the week with superb cuisine inspired by Tuscan flavors. 

Days 2-3 Descend on quiet roads into the Arno River Valley  as you pedal the Strade del Vino Terre di Arezzo toward the heart of the Chianti, passing through legendary wine villages like Gaiole in Chianti  Ride into the Crete Senesi, an area known for pecorino cheese  Explore Siena's medieval back streets and stunning piazza del campo, home to Italy's most important horse race, Il Palio  Learn the nuances of Tuscany's renowned red wines at an exclusive sommelier-led tasting at Borgo San Felice before heading to an osteria dinner.

Day 4 Cruise the ridge to ancient hilltop Radda, a cycling epicenter and former capital of the Antica Lega del Chianti (Old Chianti League)  Visit the neighboring (and rival!) villages of Gaiole and Castellina in Chianti, connected by immaculate roads and plenty of ups and downs  Settle into luxury with a world-class spa treatment at Castello del Nero  Celebrate Tuscan-style with a Michelin-starred dinner at the hotel's La Torre restaurant.

Days 5-6 Point your wheels toward the Colli Fiorentini, northern Tuscany's slice of Chianti wine production  Pedal the verdant Elsa River Valley to the spectacular World Heritage town of San Gimignano, crowned by 13 towers  Celebrate la dolce vita over a glass of refreshing vernaccia white wine, a Tuscan favorite, before heading to Florence.

Despite the record temperatures in 2015, the trip was an amazing combination of quality cycling and cultural immersion. Our leaders were well-versed in all aspects of the region: culture, architecture, economics, and culinary. Our second Backroads trip and we are already planning our 3rd in 2017!
C. Garland - Park City, UT
$4,798 - $5,248
pp dbl. occ.
(+$1,260 to $1,660 for sgl. occ.)


6 days, 5 nights
Route Rating

Open 7 Days a Week
6 am - 6 pm Pacific time

Start / End
Florence, Italy

All breakfasts, 4 lunches, 4 dinners included


C Classic Dates


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Premiere 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.

800-462-2848 Open daily, 6 am - 6 pm Pacific time

Il Borro

Il Borro

San Giustino Valdarno (1 night)

This family-owned hotel resides in a stunning setting atop a narrow ridge and features an acclaimed winery. A Relais & Châteaux member. (pool, spa)

Borgo San Felice

Borgo San Felice

San Felice (2 nights)

Described 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)

Castello del Nero

Castello del Nero

Tavarnelle Val di Pesa (2 nights)

A castle with a Michelin-starred restaurant steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)  

Guest Reviews

There's no better way to find out about Backroads than by hearing it from the people who have traveled with us. For more about the Backroads Experience, read our Guest Testimonials.

800-462-2848 Open daily, 6 am - 6 pm Pacific time


by PowerReviews
Tuscany Bike Tour

(based on 7 reviews)

Ratings Distribution

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  • 4 Stars



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  • 1 Stars




of respondents would recommend this to a friend.

Reviewed by 7 customers

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Highest Quality We Have Come To Expect. No Disappointments!


from Park City, UT

Verified Buyer

Comments about Tuscany Bike Tour:

Despite the record temperatures in 2015, the trip was an amazing combination of quality cycling and cultural immersion. Our leaders were well-versed in all aspects of the region: culture, architecture, economics, and culinary. Our second Backroads trip and we are already planning our 3rd in 2017!


Unforgatable trip!


from São Paulo, Brazil

Verified Buyer

Comments about Tuscany Bike Tour:

It was a fantastic trip! Great leaders! The rides were challeging but not impossible I would recomend this trip to all my friends, for sure


Great Times in Tuscany


from New York

Verified Buyer

Comments about Tuscany Bike Tour:

You guys did an excellent job on this trip! Beautiful hotels with great amenities, great riding, excellent leaders and delicious food. Keep up the good work!


Fantastic trip !


from Montreal, Canada

Verified Buyer

Comments about Tuscany Bike Tour:

Excellent trip all around,everything was first class! Our leaders were both fantastic. One of our best vacations ever !


Return as soon as possible


from Curitiba, Brazil

Verified Buyer

Comments about Tuscany Bike Tour:

Great TEAM, great accommodations, great support.
Will return!


Great !!


from Porto Alegre-RS/BRAZIL

Verified Buyer

Comments about Tuscany Bike Tour:

It was pefect trip! I've only have a problem with bugs bite (Im alergic ) but everthing else was terrific!!


Let's Do That Again!


from Fairbanks, Alaska

Verified Buyer

Comments about Tuscany Bike Tour:

My husband and I had a fabulous time in Italy celebrating our 30th wedding anniversary using Backroads! The trip was fun and exciting -- we will be using Backroads again. The guides with us were helpful, knowledgeable, and engaging. Some of the people we met on the trip have remained in contact and become friends. If you are thinking an active vacation is what you want to do, go with Backroads. You won't regret it.

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Dates & Prices

The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind—you won't be charged to transfer to a different trip before your final payment is due.

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

800-462-2848 Open daily, 6 am - 6 pm Pacific time


Interested in a Private Trip? Check out the Make It Private tab for private dates available, or call us at 800-462-2848.

This Trip Is Rated Levels 2-4

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.

800-462-2848 Open daily, 6 am - 6 pm Pacific time

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 20 1100 26 2000
2 22* 2200 35* 3000 40 4100
3 25* 1900 30* 2100 39 3100
4 24* 2100 36 2800 40 3900
5 19* 1700 26* 2200 42 4100
6 14 1100


* Includes shuttle.

Learn more about how we determine our route ratings and fully support a range of abilities and interests.

Please note that our distance and elevation figures come from Ride with GPS. Other sources (such as Map My Ride and Garmin devices) may give differing elevation figures due to different GPS and mapping technologies. Readings from a Garmin or a smart phone are influenced by other factors such as air pressure.

Why Travel with Backroads in Tuscany

You Get the Most out of Tuscany

Our perfectly planned routes and legendary on-trip support free you to focus on enjoying your rides through stunning Tuscan landscapes, following cypress-lined roads as they wind among sunbaked hilltop villas. No other biking company covers as much of Tuscany as we do. But just as importantly, we've figured out how to ensure the experience is captivating, not grueling – with three leaders and two vans always there to back you up.

Only the Best Hotels

On this Premiere Inn trip, you can count on the best lodgings Tuscany has to offer. In fact, the hotels we've chosen in this region have higher retail room rates than those offered by any other active travel company—even when their trips cost more.

Great Bikes Included (or Upgrade)

Choose a Backroads Custom Titanium or Custom Electric Assist bike—both are included in your trip price. Maybe a Specialized carbon-fiber pro model is more your speed or go for double fun on a tandem. Our fleet is the best in active travel, so you don't have to roll the dice on this vital trip component. Learn why our titanium bikes are ideal for most riders. See the bike options for this trip.

Navigate Your Way in Tuscany

Your ride comes equipped with a Garmin Edge Explore 1000, the best bike-touring GPS device on the market. This is a Backroads exclusive, and it's included with your bike in Tuscany. If you prefer to bring your own device, we also have downloadable GPS files and of course, our good old paper directions are always available. Read more on why our navigation options are the best.

We Live in the Neighborhood

Our Trip Leaders in Tuscany live in the area and are deeply engaged in their communities, giving them unique inside knowledge they're happy to share in making your experience that much richer. They'll introduce you to people, customs and parts of town you'd likely never encounter on your own—and teach you a few local phrases to help break the ice.

Everyone at Their Own Pace

We design and support our Tuscany trips to suit mixed abilities and varied interests—so you can set your own pace, then change things up as the day unfolds. And all guests are free to do the same, traveling together or apart, with no one cramping anyone else's style. Which sounds easy in theory, but it's hard to pull off. Here's more on how we do it.

A Variety of Routes Each Day

In Tuscany you head off each morning after choosing among several expertly designed routes—all with detailed directions, mileage and shuttle options. Unlike trips with one fixed daily route (or worse, one guide that everyone's obliged to follow), you're free to enjoy the best of the region at your pace, stopping wherever you want to explore further.

Our Cultural Roots Run Deep

Thanks to our extensive connections in Tuscany, Backroads takes you off the beaten track and deep into the region's culture in ways that traditional travel can never hope to do. We know the people and their customs, the legacy of art and architecture, the complex history and politic—and if we're not sure, our amazing local experts can fill in the blanks.

A Second Van When You Need It

Backroads is the only active travel company providing two support vans in Tuscany—because we know it's essential to ensure a truly great travel experience. It doubles our ability to be there when you need us to offer hydration, lighten your load or give you a lift if it's time to take a break. Read more on why two vans make all the difference.

More Leaders to Support You

On our Tuscany trips we have an extra leader supporting you along the road—for a total of three, compared to the industry standard two. So we can be in more places at once, giving personal attention to guests traveling at their own pace. Here's more on our Trip Leaders.

In Europe Since 1988

Backroads has been welcoming active travelers to Europe since before the Berlin Wall came down. Today it's virtually our second home. We know the perfect roads and trails, the most scenic valleys and hilltop towns, the hidden churches and gem-like museums, the up-and-coming vintners and celebrated chefs—and, of course, all the best places to stay.

We've Set the Standard

For nearly four decades we've worked to earn and maintain our right to call Backroads the world's #1 active travel company. In pursuing that vision on behalf of our guests, we believe we've set the standard for our industry—captured in the Backroads Quality Guide, which clearly sets out the benchmarks of excellence, choice and support that we live by

Your Trip Will Run. Period.

Under our Book with Confidence policy, your Backroads trip will run even for one or two people (or a family of three or four), subject to a nominal extra fee. Or transfer to another trip, and we'll give you a credit. It's all part of our trademark commitment to treating guests with integrity, transparency and total accountability. Read all the details.

We Know Where We're Going

Tom Hale has been keeping Backroads on track, with one eye on the horizon, since 1979. His passion for active travel, and for ensuring the highest-quality travel experience, is evident in every detail we add to make a guest's trip unforgettable—and the fact he's right there in the office, making it happen. To hear Tom describe his vision, watch our video.  

800-462-2848 Open daily, 6 am - 6 pm Pacific time

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 the selection of dates below for your group; some dates are only available for 16 or more guests while other dates are available for 8 or more guests. If your party has fewer than 8 guests, or your preferred date is not available, we'll create a departure just for you. Call or email us to reserve your date.

800-462-2848 Open daily, 6 am - 6 pm Pacific time

Pricing for Private Trips


  • 10 or more guests: from $4,798 pp dbl occ
  • 8 - 9 guests: from $5,198 pp dbl occ
  • 6 - 7 guests: from $5,998 pp dbl occ
  • 4 - 5 guests: from $6,498 pp dbl occ
  • 2 - 3 guests: from $7,298 pp dbl occ


  • 10 or more guests: from $4,798 pp dbl occ
  • 8 - 9 guests: from $5,298 pp dbl occ
  • 6 - 7 guests: from $6,798 pp dbl occ
  • 4 - 5 guests: from $7,398 pp dbl occ
  • 2 - 3 guests: from $8,598 pp dbl occ

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


Don't see your ideal travel date? Make a Date! i

Other Trips in Tuscany

Easy to Book Private Trips

Invite your family and friends on an adventure that's entirely your own - for your group of 8 or more. Find out more