Walking & Cycling Holidays in Tuscany Walking & Cycling Holidays in Tuscany Walking & Cycling Holidays in Tuscany Walking & Cycling Holidays in Tuscany Walking & Cycling Holidays in Tuscany Walking & Cycling Holidays in Tuscany

Walking and Cycling Holidays in Tuscany

Tuscany means art, culture, rolling vineyards, cypress trees and ancient hill villages. Sherpa Expeditions offers a range of walking and cycling holidays through the gentle landscapes of Tuscany take you through a countryside that is timeless. Tuscany is a region well suited to a gentle pace of walking and cycling and you will enjoy a varied countryside of rolling hillsides, vineyards, olive groves and forests alive with colour. Here are also some of the best preserved medieval towns in Europe with their Romanesque and gothic churches and buildings. Tuscany offers many gastronomic delights: pecorino cheese, wild boar and porcini mushrooms to name but a few. It is also Chianti wine country with several wine tasting opportunities. 



Spring in Tuscany usually starts in the second half of March when the vegetation starts to come back to life, making April and May the two months when the colours of the flowers are at their most vibrant. If you are planning to visit over this period, we’d recommend avoiding the days around Easter and the first of May, as these times tend to be quite crowded. 

Walking the countryside of Tuscany is often quiet and peaceful, even in the high season (between June and September), but in the towns it can be quite busy. After the hot summer days the air again becomes pleasantly fresh in September and October and the walking is fine, but it is in the second half of October or early November that you are most likely to experience the picturesque morning fog that the region is famous for. 

For our cycling holidays in Tuscany the month of June or September offer warm days and a lower risk of rain. Those who would love to cycle between poppies and sunflowers should travel to Tuscany in July or August and start their ride each day in the early morning to avoid the heat of midday. If you would like to avoid the main season November is a great time when you can enjoy misty sunrises, quiets roads and towns and you can test the fresh pressed olive oil on your "Ribollita" after a bath at the thermal pools of Bagno Vignoni. 


Self-Guided Walking Holidays in Tuscany 

From remote mountain walking in the Apuan alps, to some of the finest preserved medieval cities in the Amiata hills south of Siena and our highlights trips from Florence, there is truly something to appeal to anyone looking for a European walking holiday. 



Enjoy a guided walking holiday in Tuscany from Florence to Siena, two of the most important Tuscan cities, on our Classic Tuscany Guided Walk. Between Florence, the city of Leonardo, Giotto, Dante and Brunelleschi, and Siena, native land of the "Palio", lies the Chianti wine region, an area of rolling vine covered hills, medieval villages and olive groves. The region is ideal for exploring on foot, experiencing the slower pace of life endemic to Tuscany and learning about the long history of wine making. 


Self-Guided Cycling Holidays in Tuscany 

Sherpa Expeditions offer a number of self-guided cycling holidays designed to help you experience the magic of Tuscany’s countryside on an enlightening cycle through the enchanting towns and landscapes that characterise the region. Every day brings with it a diversity of sites including ancient monasteries, rolling vineyards and old olive groves, castles, villas and medieval centres ripe for exploration. Flexibility is a key component with the option to choose a tarmac road or off road mountain bike route according to your level of cycle experience. At night stay in characterful family-run hotels where your hosts will introduce you to the delights of their local sites and trattorias.



For more information on visiting Tuscany we have put together a blog article 'Walking in Tuscany'Visit our blog >>


Browse Our Walking & Cycling Holidays in Tuscany