4 day walk – San Gimignano to Siena

4-day slice of Tuscany – San Gimignano to Siena

2025 Dates:  5 – 8  June 2025 (Fully Booked); 5 – 8 September 2025 (Fully Booked)

2026 Dates:  5 – 8  June 2026 (BOOKINGS NOW OPEN) ; 5 – 8 September 2026 (BOOKINGS NOW OPEN)

This is the perfect walk for those short on time but still want to experience a walk through the Tuscan landscape.  Join Walk Local and Accredited Italian Tour Guide on this four-day walk on the ancient pilgrim’s trail, the ‘Via Francigena’ through the heart of Tuscany visiting the iconic hill towns of San Gimignano, Colle di Val d’Elsa, Monteriggioni and Siena.

Starting our walk in the beautiful UNESCO world heritage hill town of San Gimignano you will be quickly immersed in the wonderful history of the region.  A city walking tour with a local guide, a welcome Aperitivo meeting your fellow walking companions followed by a delicious Italian dinner of regional favourites starts your journey to Siena.

Staying in a beautiful 15th-century monastery in San Gimignano you experience life on the road as many pilgrims have before you…with a lot more comfort.  The following day we head off on our morning walk through the beautiful Tuscan landscape to  Colle Val D’Elsa where we have antipasto and wine tastings before exploring the old town.  We enjoy a wonderful cooking class learning to make fresh pasta and sit down to savour the delights of our hard work.  On day three we walk to the wonderful circular town of Monteriggioni, walking past fields, and farms, and meeting the locals along the way.   Staying in the walled city we enjoy a wonderful food experience in a renowned trattoria after walking the wall and learning the history of this amazing town.  Just think succulent pork, freshly picked mushrooms and silky hand-rolled pasta with the local regional wine.

On our final day, we walk to Siena over the rolling hills, past cypress pines, stone villas, and a stop for lunch before heading through the gates into the historic centre of Siena, another World Heritage Site. Siena is one of Italy’s most visited tourist attractions,  famous for its cuisine, art, museums, and medieval cityscape.

Our walk ends in the evening after enjoying the best pizza ever, washed down with the local vino, overlooking Piazza del Campo.  A walk through the Italian countryside is complete.  Join us on the Via Francigena and experience the real Italy, one step at a time.