Backroads guests biking through a poppy field
Aerial view of Tuscan fields
Backroads guest biking through Tuscany
Aerial view of Tuscany
Backroads guest biking through Tuscany
Backroads guests enjoying pizza in Tuscany
Person biking through tree lined road in Tuscany.
Man posing with wine grapes.
Tuscany alleyway
Person holding red wine glass up to camera.
Bikers posing for a picture
Cup with text that reads "Biscotti"
See all photos

Tuscany Bike Tour

A Taste of Italy from Pienza to Siena & Chianti

Couples, Friends & Solos

6 days 5 nights

Activity Level: 2-5

Casual & Casual Plus Hotels

From: $3,999 - $4,449 pp dbl occ

($600 - $700 for sgl occ)

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.

Italy Tuscany Bike Tour map
Italy Tuscany Bike Tour map


Start Arezzo / End Florence

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


  • Capture a quintessential Tuscan experience, biking from south to north through a beautiful rolling landscape
  • Sample fine wines in charming enotecas 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


Accommodations may vary based on departure date.
6 Days Casual & Casual Plus Hotels
Accommodations may vary based on departure.
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, ride 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.

Exterior view of Albergo le Terme
Albergo le Terme
Bagno Vignoni
| Casual Hotel

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.

Aerial view of the Borgo Casabianca
Borgo Casabianca
| Casual Plus Hotel

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

Days 4-6

Engage in a fascinating Q&A session with a renowned local author | 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.

Aerial view of the Villa Curina
Villa Curina Resort
| Casual Plus Hotel

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

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. View cancellation policy.

Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy in USD.

October 2023
Oct 8 - Oct 13
Sold out

Looks like you’re traveling with a smaller group

Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.

Please Select a Group Size

Group size is required to show per-person pricing. Your group size can be approximate and can change.

Activity Level: 2-5

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Daily Route Options

* Includes shuttle.
Day 1
Level 2 | 23 miles | 1200 ft. gain
Day 2
Level 2 | 18 miles* | 1500 ft. gain
Level 3 | 34 miles | 2500 ft. gain
Level 4 | 47 miles | 3800 ft. gain
Level 5 | 65 miles | 5700 ft. gain
Day 3
Level 2 | 14 miles* | 1900 ft. gain
Level 3 | 27 miles* | 2600 ft. gain
Level 3 | 37 miles* | 3800 ft. gain
Level 4 | 42 miles | 4200 ft. gain
Level 5 | 51 miles | 5300 ft. gain
Day 4
Level 2 | 23 miles* | 2400 ft. gain
Level 3 | 26 miles | 3300 ft. gain
Level 4 | 43 miles | 4400 ft. gain
Level 5 | 57 miles | 5500 ft. gain
Day 5
Level 2 | 18 miles* | 2000 ft. gain
Level 3 | 30 miles* | 3700 ft. gain
Level 4 | 49 miles | 4200 ft. gain
Level 5 | 57 miles | 5500 ft. gain
Day 6
Level 2 | 13 miles | 1200 ft. gain

What's Included

Available Bike Options

The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Click the arrow to see all bike options.

Backroads Performance Road Bike
Backroads Performance Road Bike
Performance Road Bike

Included in your trip price

This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork. 

Backroads Touring Bike
Backroads Touring Bike
Touring Bike

Included in your trip price

A proven classic, this custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.

Backroads Electric-Assist Bike
Backroads Electric-Assist Bike
Electric-Assist Bike

Included in your trip price

Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+

Cannondale Synapse Pro Carbon Bike
Cannondale Synapse Pro Carbon Bike
Carbon Bike

Ride like a pro with the top-of-the-line carbon Cannondale Synapse Hi-Mod Red ETAP AXS. Delivering phenomenal acceleration and handling in a light and powerful package.
$650 rental fee; subject to availability

Co-Motion Torpedo Tandem Bike
Co-Motion Torpedo Tandem Bike
Tandem Bike

This hand-built frame features Co-Motion's custom-designed cro-moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train, and a custom, upgraded wheelset. For experienced tandem riders.
$400 rental fee

Also Included

  • All breakfasts, 4 lunches, 4 dinners
  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Ask a trip expert

Have a question and need expert advice? Our team of Trip Consultants is here to help! You can also visit our Help Center.

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