San Gimignano just keeps calling us back. I first went there with my boyfriend a few years ago for our anniversary and, as luck would have it, we stumbled upon their biggest festival. We decided there and then to come back the same festival (and anniversary) weekend the following year. When we did, he proposed! Then it became even more meaningful for us. Covid stopped us getting there last year but we got to return again this year as part of our belated honeymoon / babymoon.
San Gimignano is strikingly beautiful and I can’t stop exclaiming, “È una favola!” (It’s like a fairytale!) at every turn. It’s a medieval, walled town perched on a hill surrounded by hectares upon hectares of olive groves and vineyards. It’s known as the Town of Fine Towers due to its characteristic skyline.
As we had been there before, we knew exactly where we were going to eat and, as we’re still in the midst of a pandemic (Things are gradually reopening), everything we wanted conveniently happened to be takeaway! The first stop had to be Bazar dei Sapori which is a deli shop with lots of cinghiale (wild boar) products.
We both got cinghiale and pecorino sandwiches and my husband got a glass of chianti and we crossed the street, down to our favourite picnic spot. The lady at Bazar dei Sapori was very helpful when choosing what sandwich I could have while pregnant.
The other “must” we had to do was get gelato from Gelateria dell’Olmo which has a sign reading “The best ice cream in the world” above its entrance. I really can’t disagree. Their cremino pistacchio e passion fruit gelato is the most delicious flavour I’ve ever had. They’re two things that don’t sound like they should go together but it works. I dream about this gelato in between Tuscany trips!
San Gimignano is definitely a place for a slow day or short weekend break. It’s lovely to stroll around casually and there’s no shortage of delicious things to eat and drink in its gorgeous medieval piazzas and streets! The Museo della Tortura (Torture Museum) was quite interesting and we really enjoyed going up to the tower to look down on the rolling Tuscan hills all around. We got the San Gimignano Pass which gave access to all the civic museums.
A short walk up to the Rocca (fort) at the top of the town is a must. It leads to a little park, full of olive trees, looking out over the surrounding green hills. It’s the perfect place to have a shady sit and admire the views.
If you’re visiting San Gimignano in post-Covid Times, I highly recommend seeing if you can time your visit with the annual medieval festival called Ferie delle Messi. It’s usually on around the 15th June. During it, there is loads of street entertainment with flag-throwing competitions, medieval games and lots of merriment. Here are some photos of it from 2019 (not a single face mask in sight!).
Getting there:
San Gimignano isn’t connected by trains so having your own transport is preferable.
Closest airports:
Florence Airport (40km)
Pisa Airport (56km)
Three Pieceens of News 
San Gimignano looks fun but I imagine requires all sort of planning. After spending more time on a train going to and from Bologna this past Wednesday, I wish I could just teleport to all these places in Italy and bypass the transit 😂
Indeed! It’s so easy with a car. In theory it should just be a 2 hour bus ride from Florence but the reality of the Italian bus services might make it more complicated!