Day 1
Arrival in San Gimignano. You will have time to explore its charming streets, the Collegiate Church and the fortress while enjoying one of the world’s most famous gelatos and a good glass of local wine.
Night 1
Our preferred hotel is located in a historic building on the main square and offers beautiful views over the surrounding countryside.
Day 2
You start from Porta San Giovanni and walk through the vineyards of Vernaccia wine. The route gently climbs and descends through the countryside, passing the ruins of an ancient fortress that once protected San Gimignano from its historic rival, Volterra, whose wealth came from its silver mines. Control of trade along the Via Francigena was the real prize.
Night 2
A panoramic B&B will welcome you, followed by a traditional dinner.
Day 3
Today the landscape changes dramatically, offering wide views that stretch from the Apuan Alps in the north to Mount Amiata in the south. The open fields may be difficult to cultivate because of the slopes, but they are a spectacular sight. The ruins of two Roman amphitheaters greet you as you arrive in Volterra, the ancient Etruscan capital. Because of its history and location, Volterra is truly underrated.
Night 3
We prefer a three-star hotel with breathtaking views and a large swimming pool, perfect for relaxing after the day’s walk.
Day 4
From the small but charming village of Mazzolla, the route crosses a nature reserve offering beautiful views, including glimpses of Larderello, famous for its geothermal activity now used to generate electricity.
Night 4
Accommodation in a historic building in a beautifully renovated and welcoming B&B.
Day 5
A Romanesque church, the village of Colle Alta and the turquoise waters of the Elsa River are just some of the highlights of today’s walk. Part of the route follows the historic Via Francigena, the ancient pilgrimage road that has shaped the history of this region.
Night 5
A countryside agriturismo with swimming pool welcomes you for the evening.
Day 6
Today you can choose whether to relax or continue exploring the hills of Chianti Classico. Vineyards, cypress-lined roads and beautifully restored villages dominate the landscape of this famous wine region. As you continue, the scenery becomes increasingly spectacular, with the fortress of Monteriggioni standing as a highlight along the route.
Night 6
Return to the same agriturismo for another relaxing evening by the pool.
Day 7
The Montagnola Senese area is known not only for the famous Cinta Senese pigs but also for its hidden parish churches, castles and small villages. Legend has it that from the Villa of Santa Colomba there was once a tunnel leading all the way to Piazza del Campo in Siena – though, of course, legends are meant for dreaming.
Night 7
A comfortable three-star hotel just outside the city walls, perfectly located for visiting the historic center and accessing public transport.
Day 8
Departure after breakfast, though you may still have time to discover a few hidden corners of this unique city.
