Self-guided Tuscany Walking Holidays

A walking holiday in Tuscany is about more than just hiking. It is a chance to explore the Italian heartland, discovering dazzling Renaissance towns with magnificent art and architecture, as well as a timeless countryside of rolling hills, forests, vineyards and olive groves. Here, you can walk between some of Europe’s best preserved medieval walled towns, through pastoral landscapes that are made for discovery on foot. Quiet country lanes take you past fields of sunflowers and golden wheat, with cypress-lined avenues leading to picturesque stone farmhouses. The landscape is especially beautiful in the Spring when the flowers are at their most colourful. While in the Autumn, the morning mist creates a truly magical effect.

Of course, hiking in Tuscany also offers many opportunities for memorable culinary experiences. Tuscany’s fertile soil produces world-renowned food and wine – the Tuscans are rightly proud of their fresh pecorino cheese, porcini mushrooms and Chianti wines.

We offer three different Tuscany walking holidays:

All of our hiking trips in Tuscany include charming hand-picked accommodation, luggage transportation, detailed walking notes, maps and GPS tracks.


Tuscany: The Chianti Trail

Walking the famous wine country from Florence to Siena
5 days, 8 days

Val d’Orcia hiking

Walk among the rolling hills of Tuscany from Montepulciano to Siena
5 days, 8 days
Easy to Moderate

Via Francigena: Lucca to Siena

Walk through the heart of Tuscany in the footsteps of medieval pilgrims
8 days
Easy to Moderate