Tuscany Bike Tour

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 $4,099 - $4,349 /person

6 days

5 nights

Activity Levels 2-5

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

Casual & Casual Plus 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 Bike Tour

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 2-5

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

Casual & Casual Plus 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-Jul, Sep-Oct 2025: May-Oct

From $4,099 - $4,349 /person

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.

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Highlights

  • 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
Italy Tuscany 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 1-2

Description

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.

Accommodations

Nights 1-2

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) 
 

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

Day 3

Description

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.

Accommodations

Night 3

Borgo Casabianca
Asciano
Casual Plus Hotel

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

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

Days 4-6

Description

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.

Accommodations

Nights 4-5

Villa Curina Resort
Curina
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)

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 $4,099 - $4,349 /person

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Hotels

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.

See itinerary with Premiere Hotels

Nights 1-2

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) 
 

Night 3

Borgo Casabianca
Asciano

Casual Plus Hotel

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

Nights 4-5

Villa Curina Resort
Curina

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)

From $4,099 - $4,349 /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 $4,099 - $4,349 /person

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From $4,099 - $4,349 /person

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Dates & Prices

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

Your guest & room selections

1 adult

1 room, 1 bed

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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

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

Learn more

From $4,099 - $4,349 /person

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