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Italy - Classic Tuscany - Self-Guided Leisure Cycling Holiday

Holiday Highlights

  • Staying at Tuscan farms overlooking stunning countryside
  • Visiting the famous towns of San Gimignano, Monteriggioni, Radda in Chianti and Siena
  • Riding through wonderful landscapes, wide open fields, cypress lined hills and vineyards
  • Trying delicious regional culinary specialities
  • Sampling the best wines of Chianti, Montepulciano and Montalcino
  • Absorbing the atmosphere of San Gimignano – a UNESCO heritage site

View Holiday Schedule

Day Description Distance Ascent Meals
1 Arrival into Pisa Airport - Transfer to San Gimignano     D  
2 San Gimignano to Casole d'Elsa 18 Miles / 32 Kms Approx 500m B D  
3 Casole d'Elsa to Abbadia Isola 20 Miles / 35 Kms Approx 400m B  
4 Abbadia Isola to Radda in Chianti 19 Miles / 32 Kms Approx 600m B  
5 Radda in Chianti to Siena 27 Miles / 45 Kms Approx. 600m B  
6 Exploring the Colline Senesi 30 Miles / 50 Kms Approx 800m B  
7 Departure from Siena - Transfer to Pisa Airport     B  

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

For more information download our trip notes

Holiday Information

A fantastic cycling holiday in Italy that 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, Chianti wine and genuine Italian food. The rolling green countryside will be the backdrop for most of your ride and you'll have the chance to explore the Chianti region and the Crete Senesi which are among the most classic and beautiful areas in the whole of Tuscany.
As you cycle through Tuscany's natural beauty, you'll experience exciting riding through dense forests, rivers and the legendary routes from San Gimignano, to Monteriggioni and on to Siena.
After arriving in Pisa we'll transfer you through Tuscan landscape, arriving at your first accommodation near San Gimignano, one of the many historical towns you'll be visiting throughout the week. The subsequent days will see you following quiet roads, riding past picturesque farmhouses nestled amidst olive groves, vineyards and forests on your way to the medieval towns of Abbadia Isola, Monteriggioni, Radda in Chianti 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?
Just call us with your preferred starting dates.

For more information download our trip notes

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Grade Help
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Departure Dates:

Duration: 7 days
Return: 07/01/2050

Prices From:

€1,095 p.p.

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+39 3405730355
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Holiday Summary

7 days
Estimated flight price:


Bike Hire:
E-Bike Hire:
Hotel Upgrade:
Single Room:
Single Room Hotel Upgrade:

Holiday Details

Place to place

6 nights small hotel/agriturismi/guesthouse accommodation

5 days riding

Breakfast and 2 dinners included


Route notes and maps provided

Luggage transfers

Airport transfers

Minimum two people

Daily departures

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Skedaddle News, Views and Holiday Stories

UNESCO Italy: Cycle through history…

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

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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