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Italy - Classic Tuscany - Self-Guided Leisure Cycling Holiday

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Ride through the beautiful Tuscan countryside. DON’T MISS OUT ON AN EARLY SEASON DISCOUNT IN 2019, FROM 01 APRIL TO 30 JUNE!

Holiday Highlights

  • Staying at Tuscan farms overlooking stunning countryside
  • Visiting the famous towns of Monteriggioni, Radda in Chianti and Siena
  • Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
  • Trying delicious, regional dishes
  • Sampling the best wines of Chianti, Montepulciano and Montalcino
  • Absorbing the atmosphere of San Gimignano – a UNESCO World 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 / 29 Kms Approx 500m B D  
3 Casole d'Elsa to Abbadia Isola 20 Miles / 32 Kms Approx 400m B  
4 Abbadia Isola to Radda in Chianti 19 Miles / 31 Kms Approx 600m B  
5 Radda in Chianti to Siena 27 Miles / 43 Kms Approx. 600m B  
6 Exploring the Colline Senesi 30 Miles / 49 Kms Approx 800m B  
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

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, delicious wine and authentic Italian food.
Rolling green countryside will be the backdrop for most of your Tuscany cyling holiday 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 journey on this cycling holiday in Tuscany you'll take in its natural beauty, and experience varied riding taking you through dense forests and alongside 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. With towns oozing the Italian Renaissance atmosphere, scattered with great restaurants, superb gelaterias and the excellent wines of Chianti and Montalcino, there's no better way to explore Tuscany than by bike!
If you'd prefer to join a group trip, we have a slightly tougher version 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
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Holiday Details

Season 1: 01/04 – 30/06 – £1065 per person

Season 2: 01/07 – 31/08 – £1260 per person

Season 1: 01/09 – 31/10 – £1065 per person

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

Ask about private departures and group bookings

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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