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Italy - Tuscany Tourer - Road Cycling Holiday

Holiday Highlights

  • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
  • Staying in quality accommodation, with fantastically warm hospitality
  • Easing along the rolling hills of the Colli Sienesi
  • 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 L  
3 San Gimignano to Radda in Chianti 40 Miles / 65 Kms Approx. 1,500 Metres Approx. B L  
4 Radda in Chianti to Pienza 55 Miles / 90 Kms Approx. 1,700 Metres Approx. B L  
5 Pienza to Montalcino 28 Miles / 45 Kms Approx. 900 Metres Approx. B L  
6 Montalcino to Casole d’Elsa 50 Miles / 80 Kms Approx. 1,100 Metres Approx. B L  
7 Casole d’Elsa to Casciana Terme 45 Miles / 70 Kms Approx. 1,150 Metres Approx. B L  
8 Departure: Pisa Airport Non Riding Day   B  

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

For more information download our trip notes

Holiday Information

An easy paced road cycling holiday in Italy explores one of the country's premier cycling locations. 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. We spend our first evening in the charming medieval town of Casciana Terme, a spa town retreat scattered with great restaurants and superb gelateria.
The following morning we head south through the olive groves to the atmospheric twin-castled hilltop town of Volterra. Moving onwards we 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 we’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 we head for San Gimignano, a fascinating “town of towers” and one of the best preserved medieval settlements in Italy. 
We’ll stay here for the evening before our final day on the bikes takes us back to Casciana Terme in good time to take advantage of the town's soothing thermal waters.

For more information download our trip notes

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Prices From:

€1,645 p.p.

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Holiday Summary

8 days
Estimated flight price:


Bike Hire:
Single Room:

Holiday Details

Place to place

7 nights agriturismo/small hotel accommodation

6 days riding

Breakfasts and lunches

Guided and vehicle support

Group airport transfers

Luggage transfers

Customer Photos


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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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