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Tuscany Bike Tour

Pedal La Bella Toscana: Val d'Orcia to Chianti

Tour Duration

6D / 5N

Trip Style

Classic Guided, Signature

Activity Level

Level 3

Hotel Level

Explorer

Bikes

Trek Domane SL 7
Trek Electric-Assist Verve+
Trek Electric-Assist Domane+ SLR 7

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Starting from

$4,299.00 per person

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Embrace la dolce vita on our Tuscany bike tour, where every pedal stroke through Chianti and Val d'Orcia reveals Italy's captivating beauty.

Immerse yourself in the vibrant landscapes of Tuscany from the seat of your bike, where endless vineyards and the aromatic air enchant every sense. Tuscan hills present stunning, joyful terrains for cycling enthusiasts. Enjoy a Chianti Classico in Radda and hone your Italian cooking skills with a private pizza-making class. Discover the breathtaking scenery of the Val d’Orcia, a UNESCO World Heritage site, and the fortified town of Montalcino, renowned for its exquisite red wines. Experience la dolce vita's seductive pace firsthand on our Tuscany bike tour—a journey sure to captivate and enchant.
Also see our Tuscany Countryside Bike Tour » and our Tuscany Wine Country Bike Tour »

Trip Wows

  • Ride along quiet roads lined with cypress trees in the beautiful Tuscan landscape

  • Take part in an exclusive, private pizza-making class taught by an Italian pizza chef and using an original wood oven

  • Explore the traditional Tuscan flavors of extra virgin olive oil and Chianti Classico

  • Discover the walled medieval town of Montalcino and sample its revered red wine - Brunello di Montalcino

  • Stay in a 13th-century village that has been transformed into a charming and elegant hotel

Cypress trees in Tuscany

A quintessential Tuscan silhouette

The stunning Tuscan landscapes

Pedal through Tuscany's undulating roads lined with cypress trees—a cycling paradise where breathtaking landscapes offer a joyous ride for all.

What Guests are Saying
two people posing with matching bike jerseys in their bike helmets

This trip was better than anticipated and I had high expectations based on previous participants' reviews! I am now convinced that this is THE way to see a new country and experience its culture; by the sights, sounds, and smells only obtainable by cycling through its countryside. The support of the Trek guides made it exceptionally easy and enjoyable. A perfect way to spend our 15-year wedding anniversary! We'll be back!

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Kathy, Trek Travel Guest

Cyclist standing in front of vineyards

The rides were phenomenal.  
Great conditions, great views, great challenges, all very rewarding.  Even with selecting the long option ride, I still found the balance of down time to be great. There's enough flexibility within to make the trip YOUR OWN trip. Excellent job.

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Carolyn, Trek Travel Guest

A group pose around the black rooster symbol of Chianti in Tuscany

I cannot think of ANYTHING Trek Travel could have done to improve this trip. I use this word sparingly but, it was the perfect way to see Tuscany and it was the best vacation of my life!

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Gina, Trek Travel Guest

This is the most satisfying and accommodating vacation I've ever been on with my husband. He is the type who really needs a lot of exercise to feel right, and I am not. But Trek made it fun for us both! Thank you for a wonderful time!

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Holly, Trek Travel Guest

Cyclist riding by vineyards

Great Ride

Vescine to Radda in Chianti Loop

A valley ride where vines and olive trees give way to shady chestnut trees as the landscape subtly shifts. Stop for an espresso at the famous L’Eroica caffè.

Dates & Pricing

Book early for the best price

  • Guaranteed

  • Join Waitlist

  • Private

  • Limited Availability

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

June 8-13, 2025 Private
Reserved

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Book Now

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4299.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4399.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4399.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4399.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4399.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4499.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4399.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Hotels you`ll stay at on this date:

  1. Palazzo del Capitano
  2. Il Borgo di Vescine
View hotels

Available bikes:

  1. Trek Domane SL 7
  2. Trek Electric-Assist Domane+ SLR 7
  3. Trek Electric-Assist Verve+ 3
View bikes
$4399.00 per person

Double Occupancy

Single Occupancy from: +1,399.00

Looking to plan a private trip just for your group?

We’ve got you covered. Choose an available trip date, gather your group, and we’ll handle the rest. Here’s the private pricing for this trip:

10+ GUESTS
Price as advertised
8-9 GUESTS
+ $750 per person to trip price
6-7 GUESTS
+ $1,500 per person to trip price
4-5 GUESTS
+ $2,000 per person to trip price
2-3 GUESTS
+ $3,000 per person to trip price
1 GUEST
Call us for pricing
Book a Private Tour
*Not all scheduled dates are convertible to private groups – a small number of trips and peak season dates may be excluded or may require “buy outs” equivalent to a larger group size. Pricing, availability, and guest minimums are all subject to change at any time.
Itinerary