Tuscany Bike Tour
6 days
5 nights
Activity Levels 2-5
Casual & Deluxe Hotels
2025: May-Oct2026: May-Oct

A Taste of Italy from Pienza to Siena & Chianti
Bike 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.
Highlights
- Capture a quintessential Tuscan experience, biking from south to north through a beautiful rolling landscape
- Sample fine wines in charming enoteche and dine on handmade pastas, bruschetta and other local specialties
- Explore some of the region's most iconic towns, including Pienza, Montalcino, Siena and Radda in Chianti
- Pedal peaceful roads and green hills past picturesque Brunello, Chianti Classico and Sangiovese vineyards

StartArezzo
EndFlorence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary

Days 1-2
Experience some of the region's must-see highlights, including Pienza, a World Heritage site famous for pecorino cheese, exquisite ceramics and Renaissance architecture • After a nourishing 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 • Enjoy post-ride poolside lounging at our welcoming hotel.

Nights 1-2
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)

Day 3
Climb by bike 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 • Leave Val d'Orcia behind as you climb up the ridgeline to enter Crete Senesi area, where we reach an agriturismo with farm fresh Tuscan food • Our hotel's terrace provides an idyllic venue for a sunset aperitivo.

Night 3
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)

Days 4-6
Bike past the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings • Sun-drenched pastures dotted with sheep and crumbling stone farmhouses give way to oak woodland and olive groves • Take some time to explore Siena on your own • Ride rolling hills alongside Chianti Classico and Sangiovese vineyards • Get to know ridgetop Radda, the center of Chianti wine production • Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.





Nights 4-5
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
What's Included
See moreHotels
Adventure-Ready Hotels
Ideally located with ready access to trip activities, our Casual hotels are also known for their character and charm.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Nights 1-2
Casual Hotel
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)

Night 3
Casual Hotel
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
Nights 4-5
*Deluxe Hotel
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
Gallery















#MyBackroadsTrip
Bikes
Choose Your Perfect Bike
Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Included in your trip price
- Ideal for avid cyclists
- Redesigned for 2024
- Next gen titanium frame with carbon wheels
- Responsive, efficient and comfortable
- Drop handlebars only

Included in your trip price
- Suited for a wide range of cyclists
- Comfortable ergonomic seat
- Long wheel base adds to the bike's control and stability
- Upright handlebars only

Included in your trip price
- One of the lightest e-bikes available
- Provides plenty of power and more than enough battery
- Lower top tubes for easier mounting and dismounting
- Upright handlebars only
- Limited availability on Unplugged Bike Tours; learn more
Min. age to ride e-bike: 16+

- $400 rental fee
- Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train
- Custom upgraded wheelset
- Best for riders with some tandem experience.
Review Snapshot
by PowerReviews
Reviewed by 46 customers
Trip of a lifetime - could not recommend this company more!
The food, wine, and scenery in Tuscany is unmatched. What really made this trip though was the first-class service from the Backroads team. Miguel, Rose, Nadia, and Gianluca are all incredible people and we feel lucky to have gotten to know them on this trip. We did this trip on our honeymoon and felt the love the entire time!
An absolutely marvelous experience!
We enjoyed every moment of our Backroads cycling trip through Tuscany! Our guides, Giulia and Luca, were just fabulous - so warm, funny, and meticulous in attention to our safety and to every minute detail of the trip. We loved the itinerary. Highlights included a fascinating private tour of a contrada in Siena, delicious meals at different agriturismos, and truly beautiful 'casual' hotels! Perhaps the best part was experiencing the breathtaking landscape on a bike and feeling a tremendous sense of well-being from the challenge of those Tuscan hills. Fantastico!

Outstanding Trip-Highly recommend Backroads
The leaders were outstanding-friendly, knowledgeable, helpful, etc.. Everything was meticulously planned and coordinated. The hotels were all very nice, the meals were all good. The group also really gelled well and everyone got along great.
Yes, Tuscany is everything that people say it is and more.
I discovered this quote by Ernest Hemingway and it describes my experience on the Backroads Tuscany trip perfectly . . . "It is by riding a bicycle that you learn the contours of a country best, since you have to sweat up the hills and coast down them. Thus you remember them as they actually are, while in a motor car only a high hill impresses you, and you have no such accurate remembrance of country you have driven through as you gain by riding a bicycle."

A fantastic experience that I will remember forever
Everything was well organized, the accommodations and leaders were top notch, and I have already recommended Backroads and the biking Tuscany Tour to several friends since getting back. What I loved most was that every detail, from the bike routes to the accommodations, was well thought-out and taken care of. All I had to do was show up, relax, and bike!

Cycling Tuscany -- exceeded expectations start to finish
Fantastic trip, highly recommended, though moderately-challenging terrain so be ready if you aren't on an E-bike. Backroads supplies everything, and has thought of everything --- detailed route information, logistical support (including moving your luggage from hotel to hotel), great bikes in top-notch condition, and just the nicest and supportive leaders. The hotels are wonderful, the food is amazing, and the group size (16) was perfect --- and a great mix of ages and skill levels. Wonderful, wonderful, trip. If you're on the fence, hop off and ride, you'll love it.
Beautiful in every way!
What a wonderful trip! The Tuscan countryside is gorgeous and the food and wine is fantastic. But what makes a Backroads trip so much fun is the camaraderie of the group and the care and joy of the guides. In our case, we were led by the charming and capable Marco and Raphael, who were ably assisted on the road by Mikel and Franceso. We were two families (all adults) who had a fabulous time. Tuscany is very hilly though, and those of us on e-bikes were especially happy with our choice!

Tuscany by bike!
A fantastic trip with a professional adventure company. The guides were fantastic, accommodations gracious, biking superb, e-bikes a fantastic option, food that was a Tuscan treat.






This trip was far more than what I expected.
The whole trip was amazing, the views, the hotels, the food! Marcos, Tomasz, Francisco and Fran were awesome leaders.
Our trip to the Tuscany Region with Backroads was amazing!
Our leaders, Marco, Sherif, Frances, and Francesco made it come alive for us with their expertise, enthusiasm, and kindness. The beautiful rolling hills of vineyards and olive groves surrounding the medieval cities and towns serving fine wine, great food and robust coffee placed this on our bucket list for an ideal Italian cultural immersion. ... and Backroads delivered big time! Perfecto!
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
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