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Italy - A Taste of Tuscany - Guided Leisure Cycling Holiday

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27 Apr to 03 May - On this journey you will explore some of the best towns of the regions, including: Volterra, San Gimignano, Monteriggioni and Siena.


5% Off - Book this January to make savings on this holiday! To redeem, simply quote RIDE19 when booking. *Terms and conditions apply, contact our team for more details.

Holiday Highlights

  • Visiting the famous towns of Volterra, San Gimignano, Monteriggioni, Asciano and Siena
  • Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
  • Tasting delicious regional culinary specialities
  • Sampling the best wines of Chianti, Montepulciano and Montalcino
  • Experiencing Italian culture at its finest
  • Having an afternoon aperitivo in Piazza Campo in Siena

View Holiday Schedule

Day Description Distance Meals
1 Arrival into Pisa Airport - Transfer to Volterra    
2 Volterra to San Gimignano 25 Miles / 40 Kms Approx. B L  
3 San Gimignano to Monteriggioni 25 Miles / 40 Kms Approx. B L  
4 Monteriggioni to Buonconvento 37 Miles / 60 Kms Approx. B L D  
5 Buonconvento to Asciano 25 Miles / 40 Kms Approx. B L D  
6 Asciano to Siena 31 Miles / 50 Kms Approx. B L  
7 Departure from Siena - Transfer to Pisa Airport   B  

Meals: B = Breakfast L = Lunch D = Dinner | Please keep in mind the distances and ascent information provided are intended to be indicative and may vary from the actuals due to accommodation changes or when compared on different GPS devices and software

For more information download our trip notes

Holiday Information

This fantastic cycling holiday in Italy really showcases the beautiful Tuscan countryside. Rural Tuscany is synonymous with undulating green hills capped by medieval tile-roofed towns punctuated by cypresses, churches and stone farmhouses. The rolling green countryside will be the backdrop for most of our ride and we'll have the chance to explore the Crete Senesi and the Val d'Orcia which are among the most classic and beautiful areas in the whole of Tuscany.
As we cycle through Tuscany's natural beauty, we'll experience thrilling riding along steep valleys, dense forests, rivers and the legendary routes from Volterra to San Gimignano, Monteriggioni and on to Siena.
After arriving in Pisa we'll drive through the Tuscan landscape, arriving at our first accommodation in Volterra, one of the many historical towns we'll be visiting throughout the week. The subsequent days will see us following quiet roads, riding past picturesque farmhouses nestled amidst olive groves, vineyards and forests on our way to the medieval towns of Abbadia Isola, Monteriggioni, Buonconvento and Siena. Towns steeped in Italian Renaissance atmosphere, scattered with great restaurants, superb gelaterias and the excellent wines of Chianti and Montalcino, what better way to visit Tuscany?
Our Taste of Tuscany holiday is run as a fully guided tour with two set departures per year. However, if you enjoy a little more freedom and flexibility then we do have a slightly gentler, self-guided version of this holiday available. 

For more information download our trip notes

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Holiday Summary

7 days
Prices From:
Estimated flight price


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Holiday Details

Place to place

6 nights small hotel / agriturismi / guesthouse accommodation

5 days riding

Breakfast, lunch and 2 evening meals included

Vineyard visit and wine tasting

Guided with vehicle support

Airport transfers

Ask about private departures and group bookings

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Skedaddle News, Views and Holiday Stories

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History oozes from the very foundations of Italy, so we thought we’d catch up with our top cat here, Naomi Lindfield, to find out her favourite UNESCO-inspired cycling trips, for your chance to cycle through history… Think of Italy and aside from pizza,…

The post UNESCO Italy: Cycle through history… appeared first on Skedaddle Blog.

Last Updated: 05/12/2016