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FCO Travel Advice

Italy - Tuscany Tourer - Road Cycling Holiday

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10 - 17 May - Cycling and Chianti including time at the gorgeous San Gimignano and Montalcino on this popular Italian road cycling holiday.

+44(0)191 2651110
  • Cycling through historic wine regions and a spot of tasting
  • Staying in quality agriturismi, with great hospitality
  • Easing along the rolling hills of Montalcino
  • Riding the stunning Unesco heritage region of Val D’Orcia
  • Stopping of at the lovely San Gimignano & Montalcino
  • Chilling out with a post cycling Chianti

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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-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.

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Holiday Summary

8 days
Estimated flight price


Single Room Option
Bike Hire
Insurance - Europe 10 day

Holiday Details

Place to place

7 night’s agriturismi / hotels

6 day’s cycling

80% meals provided

Guided and vehicle support

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