Hikes in Tuscany

This rural walk takes you through nature reserves and ancient villages before climbing up to the UNESCO World Heritage Site of San Gimignano.

A lovely walk through undulating and iconic landscapes, passing wineries, vineyards and olive groves galore and finishing in the splendid hill top town of Pienza.

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele. From here, you'll begin the day's walk. 

Enjoy a glorious walk through typical Tuscan scenery, looping back round to Volterra.

Percorso ad anello, con partenza e ritorno a Campoli. Attraversa i più bei luoghi della campagna fra Mercatale, Tavarnelle e Greve: Tignanello, Pratale, Badia a Passignano, Testalepre, Torre di Luciana.

Your walking today is along trails that are some of the most beautiful along the Via Francigena.

Walk through stunning Tuscan landscapes and oak woods, which then give way to vineyards. Arrive in Gambassi Terme, located on a hill 350m above sea level. The town has been known for its production of glass since medieval times.

Today’s walk is relatively short as this gives you time to explore San Gimignano this afternoon. Once again you will be walking through the gorgeous Chianti vineyards.

Wind your way down through the vineyards and olive groves of Chianti to the flatter lands near the historic hub of hilltop Siena with it’s fantastic Duomo and the iconic scallop-shaped Piazza del Campo. 

Walk along an older version of the Via Francigena as it bypasses the Sant Antimo Abbey, one of the most striking places in Tuscany. It is an elegant Romanesque edifice and remarkably you can still hear Gregorian chants being sung inside throughout the day.

For most of the day you will be walking along a ridge with incredible views. Later this afternoon arrive in the small hamlet of Roccae d’Orcia which is truly charming.

This morning take a self-guided walking tour of Florence following the route on the Macs Smartphone App. You will spend fascinating morning exploring world-famous artwork and Florence’s top attractions.

Once more this is a relatively short walking day which enables you to spend time exploring Siena this afternoon. Leaving behind the old town of Monteriggioni, walk along trails that take you to Montagnola and Cerbaia, a medieval village now in a neglected state.

Begin today’s walk in front of the little church of  San Sebastiano and down to the little square of Cisterna. Make your way into the valley and through olive groves, clusters of oak trees and farmers fields.

En route to San Quirico d’Orcia you pass through Brunello vineyards, there will the opportunity to visit a nice winery at Torrenieri.

Depart from Siena and follow the official Via Francigena road, the Porta Romana, all the way. Please note: You will be transferred from Grancia de Cuna to Buonconvento (this shortens the walk from 32km to a more manageable 18km). 

Bask under the Tuscan sun on this circular walk from Radda, exploring churches, vineyards and the old centre of Radda in Chianti. 

Explore the iconic wine region of Chianti and visit the world-renowned Castelvecchi, and it’s neighbouring hilltop village, Volpaia.