Exploring Tuscany: Siena, San Gimignano, and Pisa

Category: Travel
September 3, 2024

Today, as I write this post, it is my oldest daughter’s 14th birthday. It’s another reminder of why I quit my job in May to focus on things like family and travel. Time goes by so fast and, in my opinion, you may as well spend it traveling. This post is about the final leg of our month-long trip to Europe this summer. We got to see some of the cutest hill towns in Tuscany there are, including Siena, San Gimignano, and a town I didn’t think I wanted to see, Pisa.

Siena

There are so many different hill towns in Tuscany, but we had to pick just a few to tour. Siena is a small town that grew up in the shadow of Florence. For some reason, it has an intense, neighborly competitive hatred towards it that Florence doesn’t seem to return. Siena is an incredibly cute city with narrow streets, a beautiful town square, a very old bank, and a cathedral famous for its marble floors. But, the most impressive thing about this town, for me, is its twice-yearly horse race called the Palio.

Siena Cathedral Floors
The Beautiful Floors of Siena’s Cathedral

Palio di Siena

Quite by accident, we ended up touring Siena the day before one of their Palio horse races. They take place twice in the summer, once on July 2nd and again on August 16th. On these days, the town covers their main square with clay, hangs mattresses to protect the buildings, and eagerly awaits a horse race in which jockeys from the different neighborhoods race for pride and a giant banner.

Contradas di Siena
Typical Street in Siena, The Contradas are Denoted by Flags

People in Siena get really into the festival. First, you’re born into a “contrada” or neighborhood, which you remain loyal to your entire life. Your parents or siblings may be part of a different contrada. When you celebrate the Palio, you might leave your family and celebrate with your contrada family instead. There are 17 neighborhoods total, most represented by an animal like a badger or a dragon with flags that line the streets. Neighborhoods feast the night before the race and spend the entire day leading up to the Palio together. The neighborhood pulls together the money to support a horse and a jockey (kind of like an ancient Home Owner’s Association fee) and there is A LOT of pride that goes into competing in and winning the Palio. It’s an incredible tradition and it only takes place in Siena. I was happy to have been able to see the main square almost ready for the race.

The Palio in Siena's Main Square
Prepping for the Palio in Siena’s Main Square

Tuscan Countryside

You could spend an entire day in any of these hill towns, but you can also buzz through them on a tour like we did. After seeing the cathedral in Siena, we drove off to a winery in the countryside of Tuscany called Arrigoni and had one of the most satisfying experiences of the trip. The winery was located in the foothills around San Gimignano and the views from the winery were stunning. The wine was very good. We ended up shipping three bottle home and finding some delicious olive oil to take back too. I’ll just let the view from the winery speak for itself.

Tuscan Countryside
Tuscan Countryside

San Gimignano

San Gimignano is a medieval town in Tuscany preserved to look much like it did in its heyday. It used to have over 72 towers covering its skyline. Rich families built them, making each taller and taller like giant phallic symbols broadcasting their family’s dominance. Today, there are only 14 towers left, but the town itself still has its old-world charm and beautiful views of the surrounding countryside. San Gimignano was my favorite hill town. If only I could erase all of the tourists there and shut down the gaudy shops and gelato restaurants that had lines sprawled across the main square so I could have it all to myself. If you walk to the back of the town there are fewer people. There is also a nice park, Parco della Rocca, that provides serenity and wonderful views. I would go back, but probably only in the off-season so I could enjoy the town with fewer people.

San Gimignano
San Gimignano
San Gimignano Street
A Rare Moment of Tranquility on a San Gimignano Street

Pisa

And our final stop on the Tuscany tour was Pisa. I didn’t want to stop in Pisa. I did want to see the leaning tower, hadn’t planned a stop as I’d always heard it wasn’t worth it. Our tour, however, had other plans so we got to see Pisa anyway. Am I glad we saw the leaning tower? Actually, yes. Am I also glad we only spent around an hour there looking at it and the surrounding cathedral and baptistry? Also, yes. It was fun to see a famous landmark. We didn’t climb the tower, but seeing it from the outside and getting our dumb pictures was really all I needed.

Leaning Tower of Pisa
We Couldn’t Resist Because….When in Pisa!

Thoughts on Italy Overall

As I mentioned in my article on Rome, we didn’t like Italy as much as we thought we would. It was crowded, hot, and the Italians clearly don’t want all the tourists there. If I ever go back, I would land in Rome and then head straight into the Tuscan countryside. Or perhaps I would spend time in the Dolomites and around Lake Como to enjoy a more relaxed atmosphere. That being said, I’m so glad I got to hike in Cinque Terre, drink wine every day, and see some of the more famous sites around Rome and Florence with Graham. But, I honestly think our money would be better spent elsewhere. I suspect it will be quite some time before we return and only during the offseason.

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About Amber Field

Amber has over 20 years of experience working in the software industry with agile software teams and specializes in creating efficient, happy teams & clients while helping them scale, execute, and work / live intentionally.
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