We spent three days in the beautiful Tuscan town of San Gimignano, nickname “San G,” in early November 2025. Although nine months have passed since then, I want to make sure to create a record of our time there in this blog for two reasons. First, we had a wonderful time and blogging about it helps me remember it. And second, I often send my blog posts to people when recommending destinations or when people ask for tips on certain places, and I know I’ll be recommending San G to anyone visiting this part of Italy and definitely have some valuable tips to share.
Arrival and Airbnb
A downside of San G is that there weren’t great public transportation options to get there. It would have involved a local or regional bus that seemed potentially hard to navigate with all our luggage. So, we rented a car in Perugia to take us to San G. This would also give us the freedom to see some of the other towns in the area. The drive from Perugia was beautiful and took about two hours. We stopped for a picnic along the way in a lakeside park in the town of Borghetto on the northwest corner of Lake Trasimeno.
Our host met us near the entry of the city walls nearest our Airbnb apartment and helped us quickly store our luggage inside the apartment entryway before leading us to free parking down the hill for the rental car. He was very friendly and welcoming. The apartment itself was perfect for our stay in an ideal location and good layout for a short time. Review below.
Exploring San G
We set out right away to explore the city inside and around the walls of San G. They date back to the 13th century and the town itself much earlier. In fact, there was an Etruscan settlement there as early as the 3rd century BC. But what San G is most famous for is its collection of medieval towers. It once had over 70 towers and there are still 14 that stand today, giving the town a completely unique look. They’re very photogenic and we enjoyed exploring the walls, the towers, and the town itself.
That evening, we enjoyed a delightful Tuscan dinner at a restaurant called Osteria Delle Catene. We shared gratinated vegetables, wild boar pappardelle, and ribollita, which is a Tuscan bread and vegetable soup that was on our must-try list. We finished the meal with an assorted dessert plate and local sweet wines. It was a great meal to start out time in Tuscany.
Volterra, Another Ancient Walled City
The next day, we had a leisurely morning before driving to Volterra, another famous old Tuscan town a 40-minute drive from San G. We found a public parking lot, Parcheggio “Gioconovo”, that wasn’t too expensive right outside the city walls. We wandered the walled part of the city while sharing a panino and then head out on a hike to some of the old Etruscan sites. It was a beautiful fall day and nice to be out in nature. We made it back to the car in the early afternoon and drove on to our next destination another 40 minutes away.
Colle di Val d’Elsa
Colle di Val d’Elsa is another beautiful medieval hill town but seems to have a different vibe from San G and Volterra. Though very old and well-preserved, the layout is longer and it feels more open. We parked at Parcheggio “Gioconovo”, a bit farther out from the main city sites but a lovely walk.
One attraction worth seeing in Colle di Val d’Elsa is the Museo del Cristallo. The town was known as the crystal capital of Italy, producing as much as 15% of the world’s crystal. The museum was very interesting and we actually learned a lot about crystal production and different types of crystal. It’s a tradition the town is rightfully proud of.
After the museum we walked through the main town square then went up to the Il Baluardo viewpoint and walked through the older part of town. We decided we wanted another museum experience so visited the Museo San Pietro, a museum of the city’s sacred art. It was very worthwhile and interesting.
We then drove back to San G, stopping at a supermarket for some groceries to have our meal in that evening in our cozy Airbnb. I believe we picked up a couple of premade soups to heat up and some salad.
Hike Around San G
The next morning, we set out around 9:30 (basically once the fall temperature was bearable) to do a hike around the town of San G that Chad had worked out with ChatGPT. The hike provided great views of the city on the hill and all its towers and was really pleasant and beautiful. We passed pretty vineyards, people harvesting olives in the fields, and the typical Tuscan rolling hills you always think of.
We took our time with the hike, just over two hours, and made it back into San G around noon to find a hearty Tuscan pasta lunch at Locanda Del Taglierre. Arriving early (by Italian lunch standards) we got a great table looking out over the hills. We followed up lunch with gelato from the famous Gelateria Dondoli, which had apparently been featured in various travel guides and tv shows for its inventive flavors. We chose the rosemary and the chocolate hazelnut.
Other San G Attractions
I’m guessing we took a little rest after lunch before using the rest of the afternoon to visit San G’s indoor attractions. First, we checked out the free model of San G in the SanGimignano1300 gift shop. There we also found a Christmas ornament of a San G tour to commemorate the leg.
Then, we visited the San Gimignano Musei: Palazzo Comunale, Pinacoteca, Torre Grossa (town hall, art gallery, and big tower). Though the museum isn’t very extensive, it was very worthwhile for providing some context to San G and it’s towers. We started in the town hall room, which had exhibits commemorating a visit in 1300 from Dante Alighieri (famous for writing The Divine Comedy, which Chad and I both read in college). Then we checked out the art and frescoes in the rooms adjacent to the tower and as we ascended. Finally, we reached the top of the tower for great views across the city.
Before heading home, we splurged on a second gelato, this time from Caffetteria Gelateria dell’Olmo across the square from Gelateria Dondoli, because its line was far too long. This less-famous gelateria had just as interesting flavors – we go saffron and pumpkin – and we found it just as tasty. We ended the day with another casual meal in, this time with salad, beets, cheese, and bread. The next day we packed up and drove back to Perugia to return the rental car and take the train to Rome.
Summary
Our three days in San G were very much a vacation for us and we had a wonderful time. There are many preserved medieval cities in Tuscany but the towers made San G feel extra-special. The early November weather was crisp but nice with lots of sunshine and the history and architecture we experienced was unforgettable. I highly recommend visiting San G when in the area of Tuscany and especially recommend exploring the region by car and doing a hike around the city. I honestly wouldn’t change a thing about our three days there.
Airbnb Review – This was an excellent apartment for our three-night stay. It is just inside the city walls so it is very convenient to excellent restaurants and all the attractions. Federico communicated with us well before and during the stay and met us and helped us find free parking after unloading our luggage. The kitchen had the basics, though no skillet. The wifi worked well enough for streaming and video calls.