This 10-day trip takes us through the heart of one of the most iconic areas of Tuscany. The Val d’Orcia, a UNESCO World Heritage site, is part of the agricultural hinterland of Siena, redrawn and developed when it was integrated in the territory of the city-state in the 14th and 15th centuries to reflect an idealised model of good governance and to create an aesthetically pleasing picture. Very little has changed since then, as still today the Val d’Orcia comprises a network of farms, villages and towns reflecting the Renaissance agricultural prosperity, the mercantile wealth of Siena, the need for defence, and a utopian aesthetic. 

Over the course of a week, we enjoy a continuous walk amongst this incredibly unique landscape following good paths, farm tracks and strada bianche (white compacted gravel roads) through secluded valleys and ravines, vineyards (producing some of the best wines in the world) and olive groves, hay meadows and pasture fields with livestock, flat chalk plains and islands of shady woodlands, and, of course, avenues of cypress trees. We come across magnificent farmhouses, medieval castles, abbeys, inns, shrines, bridges, ancient water mills, thermal springs and visit some of the most important hill towns in the area such as Montepulciano, Pienza, San Quirico d’Orcia and Montalcino, as well as several other lesser-known gems.

After crossing the Val d’Orcia, we continue west to the Argentario promontory to embark on a 16 km ferry crossing to the Island of Giglio, where we spend the final 3 nights of the trip. This 21 sq km island in the Tyrrhenian Sea is just one of seven that make up the Tuscan Archipelago (also a National Park), and is generally overshadowed by its larger neighbour to the north, the Island of Elba. It is a predominately mountainous island made up of almost entirely of granite and culminating in the Poggio della Pagana, which rises to 496 m (1,627 ft). It has only three (picturesque) small villages and is remarkably unspoilt, with 90% of its surface covered by Mediterranean maquis, alternating with large pine forests and numerous vineyards which produce the local Ansonaco wine. Over the course of three full days, we explore virtually every corner of the island, making the most of its excellent network of paths and historic mule tracks, whilst delighting in its aromatic scents, sea breezes, turquoise waters, small sandy beaches, magnificent views, unforgettable sunrises and sunsets, rural architecture, interesting geological features, fertile orchards, lovely dry-stone walls and, of course, its delicious fresh seafood and excellent wine.

For a detailed itinerary and/or further information, please contact us at [email protected]


Fitness Level3
Cost pp
Single S.
AirportRome Fiumicino