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Italy - Tuscany Tourer - Self-Guided Road Cycling Holiday

Holiday Highlights

  • Cycling through historic wine regions with a spot of wine tasting
  • Staying in quality agriturismi, with fantastically warm hospitality
  • Easing along the rolling hills of Montalcino
  • Riding the stunning Unesco heritage region of Val D’Orcia
  • Stopping off at the lovely San Gimignano and Montalcino
  • Chilling out with a post ride Chianti

View Holiday Schedule

Day Description Distance Ascent Meals
1 Arrival: Pisa Airport Non Riding Day    
2 Casciana Terme to San Gimignano 45 Miles / 70 Kms Approx. 1,300 Metres Approx. B  
3 San Gimignano to Radda in Chianti 40 Miles / 65 Kms Approx. 1,500 Metres Approx. B  
4 Radda in Chianti to Pienza 55 Miles / 90 Kms Approx. 1,700 Metres Approx. B  
5 Pienza to Montalcino 28 Miles / 45 Kms Approx. 900 Metres Approx. B  
6 Montalcino to Casole d’Elsa 50 Miles / 80 Kms Approx. 1,100 Metres Approx. B  
7 Casole d’Elsa to Casciana Terme 45 Miles / 70 Kms Approx. 1,150 Metres Approx. B  
8 Departure Non Riding Day    

Key: B - Breakfast, L - Lunch, D - Dinner

For more information download our trip notes

Holiday Information

An easy paced self-guided road cycling holiday in Italy, which explores the Tuscan region's premier cycling routes. Tuscany - the word itself is evocative, conjuring images of classic Italian landscapes, rolling hills, cypress trees and medieval hill-top towns. 
The region also offers superb cycling and is an international training ground, attracting riders from all over the world. Cycling is a way of life here and is taken seriously. You spend your first evening in the charming medieval town of Casciana Terme, a spa town retreat scattered with great restaurants and superb gelateria.
Each day your luggage will be transfered for you so you only need to think about enjoying riding from place to place and where you will be eating your next gelato!
So to kick off your tour, the following morning you head south through the olive groves to the atmospheric "Town of Towers" of San Gimignano. Moving onwards you ride into the Parco Della Val d’Orcia, a World Heritage site with a distinctive landscape of conical hills rising from the flat chalk plains. Wine-lovers will be in their element as the tour progresses and you’ll be spending evenings in both Montalcino and Chianti where we will set time aside for a glass or two of Brunello and Classico. Travelling north again through the land which lies between Siena and Florence you head for Casole D'Elsa, one of the best preserved medieval settlements in Italy.
Your final day on the bike takes you back to where you started and you should arrive in Casciana Terme in good time to take advantage of the town's soothing thermal waters, before you prepare yourself for the flight home the following day.

For more information download our trip notes

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Duration: 8 days

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Holiday Summary

8 days
Estimated flight price:


Bike Hire:
Single Room Option:

Holiday Details

Place to place

7 nights small hotel accommodation

6 days riding

Breakfast included


Route notes and maps provided

Luggage transfers

Airport transfers

Daily departures

Minimum 2 people

Customer Photos


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Skedaddle News, Views and Holiday Stories

Design your dream cycling holiday

Looking for something a little bit different? Look no further than our Tailor Made tours! Designed with you specifically in mind, we’ll do our very best to help design the trip of your dreams. What we can offer… With over…

The post Design your dream cycling holiday appeared first on Skedaddle Blog.

Last Updated: 18/07/2016

Skedaddle Italia Srl is registed Tour Operator in Italy. Registred No. 406, VAT No. 03592410926. Reg. office: Via Caravaggio 10, Assemini, 09032, Sardinia, Italy

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