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Holidays that move you

Italy - Classic Tuscany - Self-Guided Leisure Cycling Holiday

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DON’T MISS OUT ON AN EARLY SEASON DISCOUNT THIS APRIL TO JUNE! Ride through the beautiful Tuscan countryside.

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 Meals
1 Arrival into Pisa Airport - Transfer to San Gimignano    
2 San Gimignano to Casole d'Elsa 19 Miles / 30 Kms Approx B  
3 Casole d'Elsa to Abbadia Isola 19 Miles / 31 Kms Approx B  
4 Abbadia Isola to Radda in Chianti 19 Miles / 30 Kms Approx B  
5 Radda in Chianti to Siena 27 Miles / 43 Kms Approx. B  
6 Exploring the Colline Sienesi 30 Miles / 49 Kms Approx 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 visting 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?
If you'd prefer to join a group trip, we have a slightly tougher versison of the route available. Please check out our Taste of Tuscany tour! 

For more information download our trip notes

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Departure Dates:

Duration: 7 days
Return: 07/01/2050

Prices From:

£995 p.p.

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Holiday Summary

7 days
Prices From:
Estimated flight price


Bike Hire
Electric Bike Hire
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Holiday Details

Season 1: 01/04 – 30/06 – £995 per person

Season 2: 01/07 – 31/08 – £1135 per person

Season 1: 01/09 – 31/10 – £995 per person

Place to place

6 nights small hotel/agriturismi/guesthouse accommodation

5 days riding

Breakfast included


Route notes and maps provided

Luggage transfers

Airport transfers

Minimum two people

Daily departures

Ask about private departures and group bookings

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Skedaddle News, Views and Holiday Stories

A cycling classic! Two wheels in Tuscany

With its quaint medieval towns, intoxicatingly tasty local fare and some of the most idyllic scenery you’ll encounter in Italy, it’s little wonder Tuscany is a must-visit destination. Now, imagine pedalling through these perfectly manicured landscapes, soaking up all the stunning sights and sounds on offer! Need more convincing? Time to read on… You say: ... 

Last Updated: 31/05/2018