Backroads Tuscany Italy Bike Tour
Backroads Tuscany Italy Bike Tour
Tuscany Bike Tour - Siena Piazza del Campo
Tuscany Bruschetta, Italy
San Gimignano Landscape, Tuscany, Italy
Drinking wine in Tuscany
Backroads Tuscany Bike Tours
Tuscany Bike Tours
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Tuscany Wine Country Bike Tour

Cuisine, Culture & Chianti in the Heart of Italy

Couples, Friends & Solos

6 days 5 nights

Activity Level: 2-4

Premiere Hotels

From: $6,199 - $6,699 pp dbl occ

($1,750 - $2,300 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. Imagine the wines, flavors and luxuries you'll discover.

Italy Tuscany Wine Country Bike Tour map
Italy Tuscany Wine Country Bike Tour map


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 remarkable Crete Senesi and beyond
  • Luxuriate at handpicked hotels that represent Tuscany's finest, from elegance in Castelnuovo Berardenga to unforgettable COMO Castello del Nero
  • Taste Chianti Classico and Vernaccia, among other critically acclaimed regional wines that have been cultivated in the region for hundreds of years
  • Discover idyllic hilltop towns like San Gimignano and Siena, brimming with character and stunning examples of medieval and Renaissance architecture


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 adventure, riding scenic routes in the Chianti Classico wine region | Spin through the rolling countryside and take in the sweeping vistas—you’ll soon realize why this is one of the most famous regions in the world | 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 Berardenga | 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.

Exterior of the Hotel Le Fontanelle
Hotel Le Fontanelle
Castelnuovo Berardenga
| Premiere Hotel

Experience the essence of Chianti at this hilltop retreat encircled by the quiet Tuscan countryside. World Luxury Hotel Awards winner. (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.

Pool Como Castello De Nero
COMO 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)  

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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: 2-4

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 2 | 22 miles* | 1800 ft. gain
Day 2
Level 2 | 18 miles* | 1800 ft. gain
Level 2 | 22 miles* | 2400 ft. gain
Level 3 | 35 miles | 3400 ft. gain
Level 4 | 43 miles | 4400 ft. gain
Day 3
Level 2 | 27 miles* | 2200 ft. gain
Level 3 | 33 miles* | 2500 ft. gain
Level 4 | 47 miles | 4000 ft. gain
Day 4
Level 2 | 22 miles* | 2100 ft. gain
Level 3 | 33 miles | 3400 ft. gain
Level 4 | 44 miles | 4400 ft. gain
Day 5
Level 2 | 15 miles* | 1600 ft. gain
Level 3 | 36 miles | 3300 ft. gain
Level 4 | 43 miles | 4000 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! 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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