Tuscany Wine Country Bike Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Older Teens & 20s Best for ages 17-23 (min. age 14)

Families with Teens & Kids Best for ages 9-17 (min. age 4)

From $6,199 - $6,999 /person

6 days

5 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere Hotels

Premiere Hotels - From lavish luxury to on-trend boutique, offering experiences as unique as the regions we explore.

Casual Plus Hotels - A step above Casual but not quite Premiere.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

Tuscany Wine Country Bike Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Older Teens & 20s Best for ages 17-23 (min. age 14)

Families with Teens & Kids Best for ages 9-17 (min. age 4)

6 days

5 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere Hotels

Premiere Hotels - From lavish luxury to on-trend boutique, offering experiences as unique as the regions we explore.

Casual Plus Hotels - A step above Casual but not quite Premiere.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

2024: Jun, Aug-Oct 2025: May-Oct

From $6,199 - $6,999 /person

Cuisine, Culture & Chianti in the Heart of Italy

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.

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Highlights

  • 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
Italy Tuscany Wine Country Bike Tour map

Italy

Start Arezzo

End Florence

Airports & Travel details*

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

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Itinerary

Days 1-3

Description

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.

Accommodations

Nights 1-3

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)

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Days 4-6

Description

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.

Accommodations

Nights 4-5

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)  

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

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What's Included

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From $6,199 - $6,999 /person

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Hotels

World-Class Hotels

Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

See itinerary with Casual Hotels

Nights 1-3

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)

Nights 4-5

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)  

From $6,199 - $6,999 /person

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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.

Backroads Performance Racer 2.0
Backroads Next Generation Performance Road Bike

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
Backroads Touring Bike
Backroads Touring Bike

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
Backroads Electric-Assist Bike
Backroads Electric-Assist Bike

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

Min. age to ride e-bike: 16+

Cannondale Synapse Pro Carbon Bike
Carbon Bike
  • $650 rental fee; subject to availability
  • 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
  • Built for hard-core riders
Co-Motion Torpedo Tandem Bike
Tandem Bike
  • $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.

From $6,199 - $6,999 /person

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From $6,199 - $6,999 /person

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Dates & Prices

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.

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

Download & Share

Book with Confidence

Backroads provides flexible booking policies so that you can plan your vacation with complete peace of mind.

Learn more

From $6,199 - $6,999 /person

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