• Tuscany cycling tours
  • Backroads Tuscany Bike Tour
  • Backroads Tuscany Bike Tours
  • Tuscany bike tour
  • Tuscany Bicycle Tours

Tuscany Bike Tour

A Taste of Tuscany from Pienza to Siena & Chianti

  • Capture a quintessential Tuscan experience from south to north
  • Sample fine wines before dining on local specialties
  • 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

Pedal from one unbelievable view to the next. Marvel at extraordinary 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 happy to report that everything you've heard about Tuscany is true.

Tuscany Italy Map


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 a spread of Tuscan specialties, 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 | Take some time to 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.

It was an 11 out of 10! Very Very well organized and executed. A great experience, I would highly highly recommend!
mcamm - Boston, MA
$3,198 - $3,598
pp dbl. occ.
(+$620 to $650 for sgl. occ.)


6 days, 5 nights
Activity Level

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

Start / End
Arezzo, Italy/Florence, Italy

All breakfasts, 4 dinners, 3 lunches included


C Classic Dates


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Casual Hotels

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

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)

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)

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 10 reviews)

Ratings Distribution

  • 5 Stars



  • 4 Stars



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  • 2 Stars



  • 1 Stars




of respondents would recommend this to a friend.

Reviewed by 10 customers

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It was fantastic! Clearly exceeded all of our expectations!


from Boston, MA

Comments about Tuscany Bike Tour:

It was an 11 out of 10! Very Very well organized and executed. A great experience, I would highly highly recommend!


Fantastic trip through Tuscany!


from Palo Alto, CA

Comments about Tuscany Bike Tour:

Really enjoyed this trip! Went with my adult daughter and her boyfriend, and we all had a fantastic time. We're reasonably active (choosing the longest biking option each day), and had a great time: great hills and biking, hotels and meals were very nice, and the trip leaders were very fun and knowledgeable. The other guests on the trip were all interesting, and we all became friends over many meals.

We are two vegetarians and one vegan, and the Backroads crew accommodated this with aplomb at every meal: the choices for our dietary restrictions were excellent!


Lifetime memory


from Seattle, WA

Comments about Tuscany Bike Tour:

Trip filled with challenging terrain, magnificent Tuscan landscapes, delicious food, beautiful unique hotels, This trip deepened my cultural awareness of Tuscany, while growing my physical strength as we cycled the challenging hills with our fabulous fearless leaders!

It doesn't get any better than this.

Ever grateful for this experience.


Tuscany Thrill!


from Huntington, NY

Verified Buyer

Comments about Tuscany Bike Tour:

Biking through Tuscany was one of the most thrilling vacations I have ever had, competing with my climb of Waynu Piccu (higher than Machu Piccu). The staff did everything possible to help me enjoy some measure of success (I am not a biker, per se!!); the food and accomodations were top quality; the group of bikers were the finest new friends anyone could hope to make anywhere! I hope to enjoy another Backroads trip in the near future!


Tuscany is Divine!


from Portola Valley, California

Verified Buyer

Comments about Tuscany Bike Tour:

What an amazing trip! The Tuscan countryside is breathtaking! The rides were incredible and well planned. The bikes were great. The leaders were outstanding! Loved this experience so much! Oh, and the food and the wine...divine! My husband and I can't wait to go back to Italy for more BackRoads trips!


This trip is one of my favorites...


from Pernes les fontaines, France

Verified Buyer

Comments about Tuscany Bike Tour:

We had super charming and professional leaders and a group with so much to learn and enjoy from each other.
Superb landscape, riding and such a perfect way as well to taste Italian cuisine & wines!!!


Best Vacation Ever!


from Philadelphia, PA

Verified Buyer

Comments about Tuscany Bike Tour:

First class all the way. The scenery was beautiful to bike through and the accommodations fantastic. Our guides, Rene and Stefano were wonderful - friendly and full of knowledge. We didn't want the trip to end.


Can't Imagine a Better Experience ...


from Twin Cities, MN

Verified Buyer

Comments about Tuscany Bike Tour:

Starting with our initial phone call to the BACKROADS reservations department, everything was fabulous. It was fabulous fun to be part of a relatively small (10 bikers) group, although there would have been different advantages had the group been bigger. The bikes themselves were terrific. The leaders were fun as well as knowledgeable and helpful. They accommodated a very rainy day well, making adjustments as needed to ensure that the day wasn't lost without compromising safety. The food was terrific, the cultural activities enjoyable, the scenery was breathtaking. I would do the trip again in a heartbeat.


This became our new all-time favorite vacation!


from Providence, Rhode Island

Verified Buyer

Comments about Tuscany Bike Tour:

Tuscany was gorgeous, but Backroads made it crazy great. Unique inns, great meals, fabulous wine tasting, beautiful routes, and great camaraderie. But the team leaders were the "straws that stirred the drink"! Enthusiasm, energy, fun and very knowledgeable. Even when we were tired after a long ride, they cranked up the fun quotient and kept us rocking!


Amazing Experience. Can't Wait to Do Another Backroads Tour


from Dallas, Texas

Verified Buyer

Comments about Tuscany Bike Tour:

It's hard to sum up how amazing this trip was. From the excellent guides (Luca and Renee), to the camaraderie of our fellow travelers, to the gorgeous and comfortable so-called "casual" inns where we stayed (if those were casual, what the heck makes something "premiere"?) everything was top notch. And of course, we were in Tuscany, so every day was like a postcard. And the food, of course, was delicious. We loved the special little Backroads events that you won't get on your own or, I suspect, with other tour groups -- apperitivos, pizza making night, the special tour of a Contrada in Siena. And for those wary of biking so far, the support is really excellent. I never felt like the van was far away, whether it was waiting at the top of a hill with a snack, or ready to give me a quick ride up a particularly challenging hill, or happy to take me and my bike to the next town if I was done for the day. We can't wait to take another trip with Backroads (it's already been too long), maybe next time a family trip with our kids.

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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 2-5

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 23 1200
2 25* 2200 34 2500 44 3800 65 5700
3 27* 2500 42 4000 51 5300
37* 3700
4 18* 2100 31 2200 40 3100 51 3900
5 24* 2500 24* 2500 38* 3600 53 4700
64 6100
6 13 1200


* Includes shuttle.

Learn more about how we determine our activity levels 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

We Know When to Gear Down

And that applies both on and off our bikes. Your Trip Leaders can preview every curve and climb of our routes through the Tuscan hills, offering great tips to ensure your ride is smooth and rewarding – or a lift in one of the vans if you redefine "reward" to mean a cappuccino in the next village or relaxing by the hotel pool. Every choice or diversion along the way reflects our long-standing passion for this beautiful region.

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.

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.

The Value of Casual Hotels

In addition to the ideal balance of comfort and hospitality in our choice of lodgings, this trip featuring Casual Hotels includes nearly all of your meals, plus everything from cocktail receptions to the best snacks along the road. So there's rarely a need to reach for your wallet – we've got you covered.

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.

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.

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.

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.

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.

The Best Leaders in Tuscany

Backroads has the best-qualified people to lead your trip in Tuscany, and our guests back that up, rating our Trip Leaders an average of 9.75 out of 10 for all-around quality of performance. Get the facts (and no fluff) on how we recruit and develop the very best people for your trip.

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.  

Signature Backroads Picnics

Guests rave about our picnic spreads. Enjoy a welcome break in a scenic spot, or a quick refuel stop if you don't want to lose momentum. And because we have two vans, one can host lunch while the other is out providing support along the route.

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 $3,198 pp dbl occ
  • 8 - 9 guests: from $3,598 pp dbl occ
  • 6 - 7 guests: from $4,598 pp dbl occ
  • 4 - 5 guests: from $5,198 pp dbl occ
  • 2 - 3 guests: from $5,998 pp dbl occ


  • 10 or more guests: from $3,198 pp dbl occ
  • 8 - 9 guests: from $3,698 pp dbl occ
  • 6 - 7 guests: from $5,398 pp dbl occ
  • 4 - 5 guests: from $6,198 pp dbl occ
  • 2 - 3 guests: from $7,198 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

C 2018 Classic Trips
2018 June
2018 October

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