Backroads Tuscany Italy Bike Tour
Backroads Tuscany Italy Bike Tour
Tuscany Bruschetta, Italy
Tuscany Bike Tours
Backroads Tuscany Bike Tours
Tuscany, Italy
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Dates for 2023 will be added soon.

Tuscany's Chianti Bike Tour

Quintessential Tuscan Town & Country

Couples, Friends & Solos

6 days 5 nights

Activity Levels 2-4

Premiere Hotels

From: $5,999 - $6,199 pp dbl occ

($1,500 for sgl occ)

Tuscany is not only a destination, it's a sublime experience. Pause on the cypress-lined roads that overlook the vineyards and take it all in. You'll think that no view will compare to that view, until you round the next bend and see another. It's a wonder anyone ever finishes the bike rides. And this is only a preview of what you'll see on our bike tour in Tuscany. Imagine the wines, flavors and luxuries you'll discover.

Tuscany Chianti Biking
Tuscany Chianti Biking


Start Arezzo / End Florence

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


  • Bike our favorite Tuscan roads—with ample van support, of course—as we wind our way from breathtaking Chianti to glorious Siena and beyond
  • Luxuriate at handpicked hotels that represent Tuscany's finest, from Relais & Châteaux elegance in San Felice to unforgettable Castello del Nero
  • Taste Chianti and Vernaccia, among other critically acclaimed regional wines that have been cultivated in the region for hundreds of years
  • Discover idyllic hilltop towns like Montepulciano, brimming with character and stunning examples of medieval and Renaissance architecture
Tuscany Biking Tour
Tuscany Biking Tour
The Backroads Experience
The Backroads Experience
Backroads Biking Trips
Backroads Biking Trips
Backroads Trip Leader
Meet Our Leaders


Accommodations may vary based on departure date.
6 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-3

Embark on a quintessential Tuscan bike tour, riding scenic routes in the Chianti Classico wine region | Sample local specialties at an organic agriturismo before biking past olive orchards and vineyards | Ride toward the heart of the Chianti, passing through legendary wine villages like Gaiole in Chianti and Castelnuovo Berardegna | Cycle into the Crete Senesi, an area known for its lunar landscape | Explore Siena’s medieval back streets and grand 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.

Borgo San Felice
Borgo San Felice
San Felice
| Premiere Hotel

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)

Days 4-6

Ride the ridge to ancient hilltop Radda, former capital of the Antica Lega del Chianti (Old Chianti League) | Visit the picturesque neighboring village of Castellina in Chianti | Celebrate in Tuscan style over dinner | Bike to Colli Fiorentini, northern Tuscany's slice of Chianti wine production | Follow cycling routes in the verdant Elsa River Valley to the spectacular World Heritage town of San Gimignano, crowned by 13 towers | Toast la dolce vita with a glass of refreshing Vernaccia, Tuscany's most famous white wine, before heading to Florence.

Castello del Nero
Castello del Nero
Tavarnelle Val di Pesa
| Premiere Hotel

A castle-turned-Renaissance villa steeped in Tuscan charm and situated on a hilltop overlooking rolling vineyards and olive orchards in the Colli Fiorentini. (pool, spa)  

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. View cancellation policy.

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

Activity Level: 2-4

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 1 | 8 miles* | 700 ft. gain
Level 2 | 12 miles* | 1100 ft. gain
Level 2 | 19 miles | 1800 ft. gain
Day 2
Level 2 | 17 miles* | 1800 ft. gain
Level 2 | 22 miles* | 2600 ft. gain
Level 3 | 32 miles* | 2900 ft. gain
Level 4 | 37 miles | 3700 ft. gain
Day 3
Level 2 | 25 miles* | 1900 ft. gain
Level 3 | 31 miles* | 2200 ft. gain
Level 4 | 41 miles | 3300 ft. gain
Day 4
Level 2 | 22 miles* | 2000 ft. gain
Level 3 | 37 miles | 3000 ft. gain
Level 4 | 42 miles | 4000 ft. gain
Day 5
Level 2 | 15 miles* | 1600 ft. gain
Level 3 | 36 miles | 3300 ft. gain
Level 4 | 45 miles | 4300 ft. gain
Day 6
Level 1 | 8 miles* | 400 ft. gain
Level 2 | 15 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! Read on for your available bike options for this trip. (click the arrow to see all available 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, our most popular 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
NEW! Electric-Assist Bike

Included in your trip price

Our newly redesigned titanium e-bike is a lightweight yet powerful machine unique in the world of e-bikes. It provides plenty of power to flatten the hills and more than enough battery range to cover the distance.

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—it’s built for hard-core riders.
$400 rental fee

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

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