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Italy - A Taste of Tuscany - Guided Leisure Cycling Holiday

Trips to book before it's too late. For all other dates check-out the Departure Dates menu below


28 Apr to 4 May - On this journey you will explore some of the best towns of the regions, including: Volterra, San Gimignano, Monteriggioni and Siena.

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+44 (0)191 265 1110
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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 afternoon aperitivo in Piazza Campo in Siena

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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 visting 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

Give us a call on:
+44 (0)191 265 1110
Drop us an email on:
Departure Dates: Prices From:

£1,295 p.p.

Ask about our private departures and group bookings
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Holiday Summary

7 days
Prices From:
Estimated flight price


Bike Hire
Electric Bike Hire
Single Room:
Single Room:
Insurance - Europe 10 Day:
Insurance - Europe 10 Day:

Holiday Details

Place to place

6 nights small hotel / agriturismi / guesthouse accommodation

5 days riding

Breakfast and lunch included

Guided with vehicle support

Airport transfers

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Skedaddle News, Views and Holiday Stories

Travel Trends from Team Leisure…

Experiential travel > sightseeing: Never mind selfies in front of famous landmarks, the new way to experience a destination is the authentic approach. Lucky for you, all of our holidays offer the opportunity to spin a new light on your chosen destination… Norway exchange rate: Looking for a trip where your money will go further in 2016? ... 

Last Updated: 15/03/2016

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