Four-day walk along the Via Francigena in South Tuscany
From San Gimignano to Radicofani
4 days

We’re just going to say it: join the Via Francigena on this walk and you will see the very best Tuscany has to offer. The ancient pilgrim route to Rome stops at some of the most famous historical and spiritual sights in all of Tuscany: walk it to see battlements, towers, cathedrals, thermal pools and those iconic cypress tree drives.

The walking in the south of Tuscany is hilly and often hot, but utterly beautiful. We’ve included some pilgrim stays (which you’ll need a credential for – a ‘pilgrim passport’ to collect stamps in) as well as some suggestions of where to eat on your way.

Day 1
San Gimignano to Monteriggioni
 - Credit: What if we walked?

Start in San Gimignano, the famous medieval town of towers. From here you walk through vineyards, where the grapes for the famous Vernaccia wine are grown. This day is a day of undulating valleys, rural and quiet. Turn around every now and then to see the towers slowly disappear.

There are a couple of agriturismi on this route that you may be able to pop into for a drink - but best to bring a picnic anyway.

Just before Monteriggioni, with its peculiar halo battlement above you, stay at the pilgrim ostello at Abbadia Isola at the foot of the hill.

Check out here all the details about the leg from San Gimignano to Monteriggioni.


Day 2
Monteriggioni to Siena
 - Credit: What if we walked?

Explore the walls of Monteriggioni in the early morning, and have the town to yourself. The intact walls are amazing, and inside is pretty: there’s a couple of cafes and the church of Santa Maria Assunta in the central piazza. Then, walk through shady woodland for the day towards Siena - it’s a secret, clandestine route into the city and a very cool way to arrive.

There are plenty of places to stay in Siena, including a pilgrim hostel at Casa delle Balie. Spend at least a day in the city, soaking in its extraordinary atmosphere. Make sure you visit Siena Cathedral of course: if the marble exterior impresses you the inside is even more astonishing, with its giant floor murals and starry night ceiling. It’s also where you collect your pilgrim stamp for your credential - pilgrims with one gain entry to the Cathedral for free.

Just opposite the Cathedral is Santa Maria della Scala, the old pilgrim stop and hospital, now an information centre. It’s a fascinating place to have a look in, and it now sells food and coffees.

Note that if you time your walk right, you could be in Siena for the Palio horse race, held twice a year in July and August. We’d recommend it as an incredible experience.

From here, catch a local bus to San Quirico d’Orcia, a gateway town to the most dreamy Tuscan countryside.

Check out here all the details about the leg from Monteriggioni to Siena.

Day 3
San Quirico d’Orcia to Castiglione d’Orcia via Bagno Vignoni
 - Credit: What if we walked?

After a coffee in San Quirico d’Orcia walk down to Bagno Vignoni, the Roman spa town. Why not use the new thermal spa here, and have lunch afterwards by the ancient pool still steaming away in the centre of the village?

Then walk the short way up to Castiglione d’Orcia, a small town with a 13th century tower Rocca di Tentennano.

At the moment there aren’t any pilgrim stays in Castiglione, so choose from the small selection of B&Bs in the town.

Day 4
Crossing the Val d’Orcia to Radicofani
 - Credit: What if we walked?

Rise at dawn to catch the most beautiful of sights: the Val d’Orcia in the early morning. This valley is perhaps the most picturesque in all of Tuscany, and you’ll spend the day wandering right through it. Rolling landscapes, golden farmhouses and yes, those cypress trees. Starting early is also a good idea to avoid the heat as it is very exposed and there aren’t really places to stop.

The day ends with a climb to Radicofani, the last hilltop village of Tuscany, and where our walk on the Via Francigena in the south of Tuscany ends.

To leave, walk downhill from Radicofani to the main road, where there’s a bridge across a river into Lazio, where the Via Francigena continues. Stop the Tuscan side at the café for a morning coffee and wait for the bus onto Acquapendente (the next biggest city), or call a taxi to go any which way.

Check out here all the details about the leg from San Quirico d'Orcia to Radicofani.