Hike Around San Gimignano

A walk among vineyards with an incredible view

This pleasant walk will take you along the gravel roads of the Wine Road of the Vernaccia di San Gimignano – with the added plus of views of the famous medieval town with its many towers!

The walk is around 10 miles if you follow what we did, taking a longer way back to our parked car. You can always just retrace the same route on the way to San Gimignano and cut 3 miles off the total walk. We made it an entire day hike, starting around 10am, arriving in San Gimignano well before lunch, and just strolling around the town and enjoying it (as well as resting since we were backpacking with a toddler) We bought some panini for a picnic at the fortress and rested a bit more before heading back into the countryside.

We did the walk following the itinerary we found on the CAI Valdarno website which calls it a ring walk between San Gimignano and Poggibonsi. It has an altitude map as well as a .gpx file you can download.

Just note the difference between their maps and altitude and ours is that they don't take into account the walk into San Gimignano.

Again, remember to plan to do this walk during the cooler morning hours in the summer (not making it a whole day unless you're prepared to take on some heat) or during the cooler months as there isn't much tree cover along the route.

Of course, if you're a photographer and want amazing shots of the town, you should do this route much earlier in the day than we did ;-).

You can download the scanned copies of the trail maps with route: bottom and top.

Park before getting to San Gimginano

Starting point: Drive from Poggibonsi toward San Gimignano along SP1. Be on the lookout on the right side after you've left the industrial area of Poggibonsi for a winery with a lot of flags; shortly after that, there is stretch of straight road. Toward the end of that stretch, you'll find signs for Pietrafitta on the right, with a small yellow chapel with the name Pietrafitta on it and EU and Italian flags to the right. Turn off the main road here and park here. This is where you start off and return to. If you do the ring road, be prepared to walk that last part of the main road on foot along with traffic. Just be extra careful at that point.

The route you're following is strictly unpaved gravel roads, which are called “white” roads in Tuscany. You won't be going into any woods of trails off the main road, so this makes it a very suitable walk for most everyone and easy to follow.

Get started and head uphill – the whole road will alternate between soft ups and downs but the altitude difference on this first part is quite small. You'll pass by Pietrafitta and other wine estates, and enjoying beautiful views of the town of San Gimignano and the vineyards that surround the town growing white grapes for Vernaccia.

The end of the road will bring you to a small church at Casale. Here you turn left to head to San Gimignano.

Visit San Gimignano

If you've never been inside, we highly recommend you visit the interior of the Duomo to enjoy the beauty of the magnificent frescoes and then climb the Torre Grossa right next door: you'll get to see another, even more spectacular view of the entire town and the countryside from the top of the highest tower still standing in the town. Enjoy walking around the town and its two main piazzas, then head up behind the Duomo to go to the remains of its fortress called La Rocca. You can climb up one of the remaining corner towers to get a view. In the small piazza before the entrance to the Rocca, there is a small museum dedicated to the Vernaccia di San Gimignano.

Enjoy a picnic and a gelato like we did (the Gelateria Dondoli in Piazza della Cisterna has won several awards so we headed there). We eventually decided to head back following the same road we had taken to get into town to return to the small church of Casale. Right at that point, there is another road in between the church and the road we had followed earlier – take that one if you want to do the longer route. If not, take the same road back to your car.

Longer return route

If you follow the same route we took, this new road quickly goes down a valley by a small lake before climbing again. Most of the altitude difference we found in the day's hike happens on this part of the route, as you're following another set of hills and road parallel to the first road. Keep a lookout for signs for Fattoria Poggio Alloro on the right and take this road. This route has several farmhouses and a bit less vineyards but you have great views of the Tuscan countryside. You can't get much lost here, but we did manage to miss our turn off after the Castello di Fulignano and for that reason I mapped our route to show it is possible to keep going straight going through the woods. But I also marked the point where we realized later we should have turned right to reach the main road between Poggibonsi and San Gimignano. We took a longer way back along a rougher trail, so definitely take the shorter, more direct route!

In any case, in this area if you pay attention to the dirt you might even find some marine fossils! This entire area at one time a long time ago used to be covered by the sea which made it an interesting find to the end of our hike around San Gimignano. We hope you enjoy the day out as well.

We saw several B&Bs and farmhouses along these two routes which would make perfect locations to stay at just outside of San Gimginano. If you want to stay in this area, take a look at our recommendations for accommodation in San Gimignano!