Walking countryside family path

Cortona & Montepulciano – jewels of Tuscany

Cortona and Montepulciano are typical hill towns that face each other across a huge and fertile valley, the Val di Chiana. In this area you can experience and discover history and culture from the most ancient civilizations up to modern times. Passing through classic romantic Tuscan countryside, you can also discover wild areas that the typical tourist never sees. Cortona and Montepulciano are well known for their DOC wines, the most famous Nobile and Syrah. Both towns and their surroundings are filled with cantine and world-famous wineries.
The hikes will take you through a uniquely linear, almost geometric landscape of hills, vineyards, and olive trees. This area has been rendered so memorably in books and films such as Under the Tuscan Sun. You will walk through a Renaissance painting, a landscape of blue sky, golden ochers, and lush greens.
The Val di Chiana is also rich in traces of the Etruscan and Roman civilizations. We talk about paved roads, walls, gateways and tombs. These fascinating remnants can all be admired during a walking trip in the region.

Across postcard landscapes you can:

walk overlooking the shores of Lake Trasimeno.
meander into Cortona’s bustling alleys.
walk on an ancient pilgrims’ route.
discover the hermitages of St Francis.
hike over green and golden hills.
pass through fortified Medieval villages.


• The majestic “Leopoldine” country houses, so called in honor of the grand duke Pietro Leopoldo
• Lake Chiusi and Montepulciano, the gems of the valley
• The vineyards where the famous Vino Nobile is produced
• The Medieval villages of Montefollonico, Torrita di Siena, and Lucignano
• The traditional olive oil production

what people say about us

Marco knows a huge amount about everything we wanted to know – from nature to culture and history.
He has a great sense of humor and was a pleasure to have around us on our mixed day of walking, birding and wine-tasting in the Valdichiana. Natasha UK