Medieval Tuscany: San Gimignano, Monteriggioni, and Siena

There were so many medieval towns I wanted to visit in the Tuscany area, and we only had a day to do them all, so we found this one day tour to San Gimignano, Monteriggioni, and Siena via Get Your Guide and decided to try it out! I don't normally go on tours, but given the time restraints we thought this would be the best way to hit all the spots. Here are my experiences from this tour. A quick disclaimer here that this is not a sponsored post, and all views are my own!

San Gimignano

The first stop on our tour was the medieval town of San Gimignano. This UNESCO World Heritage site is walled, and is famous for its many tower homes. Our guide told us that rich families and merchants who lived there built these tower homes as symbols of their wealth and power. At one point there were probably 72 towers in this town (imagine what the skyline would have looked like at the time!), but only 14 remain today.

For a small fee, you can climb the tallest of the remaining towers, Torre Grossa. This tower was built in the 1300s and is 54 meters high. There is not much to see on the way up, but the climb is a lot easier (more spacious and less claustrophobic) than the ones for the Duomo and bell tower in Florence! The view at the top is worth the climb. You get a great panoramic view of the whole town. Your entry to the top of Torre Grossa also includes entry to the Civic Museum which includes a small gallery and a large room that was once used as a council chamber.

San Gimignano is also home to Gelateria Dondoli, located at Piazza della Cisterna . The gelato sold here is award-winning, and is hailed by some as the "world's best gelato". I tried the passion fruit, vernaccia, and macadamia flavours. They were all extremely flavourful. The passion fruit was a bit too tart for my liking, but I did really enjoy the vernaccia (which is a type of wine which San Gimignano is famous for) and macadamia ones. I don't know if I would call it the best gelato in the world though. I think I prefer the gelato from Gelateria Santa Trinita in Florence.

San Gimignano was my favourite part of the tour. I really enjoyed the atmosphere of this medieval town, and enjoyed walking down the streets, surrounded by the high walls. It felt like I had travelled back in time! 


The next stop on the tour was the Casafrassi winery. Here, we tried some Chianti Classico wine, which is symbolized by a black rooster. According to our tour guide, legend has it that back in the medieval days, Florence and Siena were fighting over who should rule over the Chianti region. They then decided that they would settle it by each sending a horseman from their cities to set off early in the morning, when the rooster crowed. Wherever the two horsemen met would be the border of the land. According to this legend, Siena picked a white rooster, and Florence picked a black rooster. Florence decided to starve their rooster, and because they did, it crowed earlier in the morning than Siena's rooster. Because of this, Florence's horseman was able to travel further and so, they got to rule over a bigger portion of the land, all thanks to the black rooster!

Interesting legend aside, I didn't really enjoy the wines we got to taste at the winery. I am more of a sweet white wine girl though, so that might be why. We also had lunch at the winery, and other than the panna cotta we had for dessert (which was amazing!), the meal was pretty average. 


The small, medieval, walled town of Monteriggioni was the next stop on our tour. Built in the 1200s by the Sienese, this fort served as an important point of defense for them since it was located so strategically on a hill. The town and walls are very well preserved, and you can even walk along the walls. Unfortunately we only had short 30 minute stop there so we didn't have enough time to do that.

Since it was November when we went, it was very quiet and many of the shops were closed. But there is a medieval festival held there every July. Our tour guide says everyone dresses up in medieval clothes, there's a parade complete with jesters, and even a medieval feast! It seems like it would be a lot of fun!

Fun fact: Some of the Assassin's Creed video games were based on Monteriggioni!


The final stop on our tour was the historic center of Siena. Also declared a UNESCO World Heritage site, Siena is famous for Palio di Siena, a bi-annual horse race that is held at the Piazza del Campo. A guide local to Siena took over here and took us on a walking tour. Unfortunately for us, it poured so we ended up huddled under shelter for part of it. My audio guide wasn't working either, so I couldn't really hear our guide. But from what I was able to hear, Siena seems like such a fascinating place with a really rich history. The fact that they still have rivalries between the 17 contrade (districts) in Siena who compete with each other in the Palio seemed like something from medieval times! 


Siena blew me away with its medieval architecture. I think Piazza del Campo (above) is a must-see. It's beautiful and massive! The buildings in the historic center also have some great gothic details, such as iron rings on the side of the buildings where horses would be tied to.

The Siena Cathedral had an amazing facade, and our guide told us it was free to enter during low season. Unfortunately, by the time we were finished our tour and had free time, the cathedral was just closing so we couldn't go in.

I was really excited to be visiting Siena, but while it was beautiful, my experience fell short of my expectations because of the weather and the timing of things. I'm putting it onto my list of places I would have to visit again if I'm ever back in Italy. Maybe during the Palio, to see the rivalry between the contrade in person!

Tour Review

As with all things, this tour had its pros and cons. I learned a lot about about the places we visited through our knowledgeable guide, and was able to get to a lot destinations in a short amount of time without having to worry about how I would get from one place to the next. The guide was also very friendly and tried to accommodate everyone as much as possible when some of the tour members wanted to skip parts of it due to the heavy rain. I also liked that they provided a local guide in Siena, because she was able to share her personal experiences as someone who has grown up in this very interesting place!

I do wish they would have timed things a bit better though. I don't think it was a good idea to pack two tour groups into the wine tasting, since half of us ended up out in the hallway and couldn't hear anything when they were describing the wines. Ending the walking tour at the Siena cathedral telling us that we could go in if we wanted, only for us to find out that it was closing, also wasn't ideal. The guide also did not change out my audio guide in Siena even though I told her that there were issues with mine and so I wasn't able to hear much.

We had a decent amount of free time to explore on our own at each of the sites which I really appreciated: 2 hours in San Gimignano, 30 minutes in Monteriggioni, and 2 hours in Siena.  Mostly, the guide gave us interesting tidbits of information about each of the locations as we were traveling there and then let us explore on own. I prefer free time over having to follow a guide everywhere. All in all, if you're looking to get a quick taste of San Gimignano, Monteriggioni, and Siena all in one day, I think this is a good tour!

Want to book this tour via Get Your Guide? Click here!

This post is linked up on: The Weekly Postcard, Monday Escapes, Our World Tuesday