Charming Tuscan Towns

We chose an agriturismo in San Gimignano as our base in Tuscany which was a great option to take day trips to the surrounding towns like Volterra and Monteriggioni but many people use Siena as their Tuscan base and if that's the case for you, these are still great day trip options!

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San Gimignano

This was my personal favorite of the smaller Tuscan towns we visited during our trip.

I had the BEST meal of my life here, as well as the BEST gelato of my life!

We stayed about a 5 minute drive outside of San Gimignano at an agriturismo called, II Segreto di Pietrafitta and we couldn't recommend this place more.

It was so idyllic with the architecture, vineyards, hills, view of San Gimignano, and the incredible service, 10/10.

Now for the actual town of San Gimignano, it is STUNNING.

A total dream. From the medieval architecture, to the food, wine, views, and just overall vibe, it's nothing short of charming.

It's the perfect place to station yourself for a Tuscan road trip.

Our favorite activity here was climbing the 218 steps up Torre Grossa.

Tickets cost 9 euros and include access to the museum. This is the tallest tower in San Gimignano built in 1311 and the views are unbeatable, absolutely incredible.

And now for the FOOD. I had the best meal of my life at Ristorante Bel Soggiorno. I can't stop dreaming about this pasta!

Get the cappellacci pasta with pistachio cream, fossa cheese, and speck. You can thank me later.

This was not just my favorite dish in Italy but it was my favorite dish I EVER had!

And now for the best gelato of my life! That would be the crema di Santa Fina gelato at Gelateria Dondoli.

I don't even know how to describe this gelato, it was so different from anything I've ever tasted and is in a league of its own!

GET THIS FLAVOR, you won't regret it. This flavor actually won the world's most famous gelato in 2024 and I understand why.

If you only have time for one of these towns, our recommendation would be San Gimignano. But you can't go wrong with any town in Tuscany!

Volterra

If you are a Twilight fan, you may remember the name Volterra and that’s because Volterra was the name of the town in Italy where the Volturi live.

Fun fact, while Volterra was the name of the town they used in the movie, the scenes weren't actually filmed here, instead they were filmed in nearby Montepulciano.

Craig had been to Volterra on his previous trip to Italy and absolutely fell in love with the town, but this was my first time.

Unfortunately we were there on a cold and rainy day so we didn't spend as much time as I would have liked. However, we made the most of our rainy morning by walking the adorable streets, checking out the amphitheater, shopping and ending our time with an epic meal in a cave!

If you love truffle, like us, this is the place to pick up all things truffle.

As you can see, even in the rain, Volterra is dramatic and stunning.

We tried to get into the amphitheater; however, it was closed when we were there so we weren't able to go inside but we were still able to get amazing views from the street level and from above.

Craig couldn't stop talking about one of his favorite meals he has ever had which happened to be at a place in Volterra called Ristorante La Terra di Mezzo so obviously we had to go!

Now last time he was here, it was a beautiful day so he ate al fresco and he never even went inside the building.

This time, it was down pouring so we ate inside and to our surprise, we followed our waitress to the basement...which was a CAVE!

Craig opted for the same exact dish he got last time, the pappardelle with truffle, ham, ricotta, and lemon.

We couldn't recommend this more! It was phenomenal!

I wish I would have gotten it but I decided on the cacio e pepe with truffle which was good but the pappardelle was on a whole other level!

After lunch, it started chucking down rain even harder so we decided to head over to Monteriggioni.

Monteriggioni

Monteriggioni is a super small little town surrounded by a medieval fortress dating back to 1213 AD.

It's so small that you could see the entire town in 5-10 minutes -- seriously! However, there are cute shops, cafes, restaurants, and wine bars to entertain you for at least a few hours.