Your Tuscan walking begin in the medieval and Renaissance hill town of Montepulciano. Montepulciano is easily accessible via Rome, Florence or Pisa; catch the train to Chiusi then take a local bus or a short taxi ride to Montepulciano. Admire the impressive views over the rolling Tuscan landscape that you’ll be exploring over the next week. 

Set off from San Biagio church on a quiet rural track and suddenly you’re lost in peaceful beauty. Soon you come upon the peaceful village of Montichiello, where you can pause for a relaxed lunch or perhaps just a quick cappuccino on the way to Pienza.
Picture-perfect Pienza is a UNESCO World Heritage Site brimming with unique Renaissance architecture. AND it is home to delicious pecorino cheese and tasty truffles. The ideal spot to indulge in Tuscan treats!

Challenge: 4 hours, 13/15 km, 385 m ascent, 505 m descent

Wander through impossibly perfect landscapes of rolling hills, majestic oaks, cypress trees and photogenic villages. Stop to rejuvenate at the hot springs in Bagno Vignoni and trade the warm Tuscan sun for steaming medicinal waters.

Challenge: 4 hours, 12 km, 195 m ascent, 420 m descent

Test your legs on a more challenging -but very rewarding- route as you follow dramatic arid ravines through wild surroundings to the remote Sant’Antimo Abbey, perfectly situated in a pastoral landscape. Take time to explore this mysterious 750 A.D. monastic site then jump in the taxi for the transfer to Montalcino.

Challenge: 5 hours, 14 km, 225 m ascent, 185 m descent

A hearty breakfast will set you up for a long but enjoy day of  walking in the famous Brunello wine region, passing vineyards and olive groves, then again entering the beautiful Tuscan landscape of the Crete Sensi and Buonconvento.

Challenge: 5 hours, 15/18 km, 316 m ascent, 619 m descent

A short day which is full of ups and downs, beginning with a transfer to the monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick and set in the rugged Tuscan landscape. After an early visit to avoid the crowd, walk back to Buonconvento.

Challenge: 5 hours, 14 km, 382 m ascent, 460m descent

A short transfer takes you to Monteroni d’Arbia then you head toward Siena on foot, hiking hills and hamlets till the city's unmistakable silhouette begins to materialize in the distance. At Arbia you catch the train into Siena, then spend the evening wrapped in its magnificent beauty: the grand Piazza del Campo, delightful Duomo and medieval palaces recalling the city’s ‘contrade’ who ride in the risky ‘il Palio di Siena’.

Challenge: 4 hours, 10 km, 225 m ascent, 185 m descent

Your self-guided walking holiday comes to an end today after breakfast. Departure from Siena.