Day Trip from Florence To San Gimignano & Siena

After convincing work to let me stay an extra week in Florence (giving me one extra weekend) I had a hard time coming up with what I should do. I have already been to a lot of the bigger cities in Italy when I was younger, and part of my really wants to re-explore them, but for this trip I decided staying close and taking a day trip driving through the Italian countryside sounded perfect!

There are WAY too many cute places to visit in the Tuscan countryside. I originally planned to go to a few more than I actually made it to, but honestly parking was terrifying hahah and as a solo traveler, I err on the side of not getting actually lost – not in the cute “she is not lost” way.

San Gimignano

I started my morning driving to San Gimignano which is on the southwest side of Florence. This town is exactly what you would picture a small walled medieval hill town to look like and is one of the most popular destinations in many guided tours from Florence. You’ll have no problem walking around starting from the Piazza del Duomo. The hub of town life in San Gimignano is the piazza where you can see both the Duomo and the Town Hall. It’s also where you can go to climb the Torre Grosso and see the town from above. I did not do this because I went so early in the morning but it would be cool if you had time.

My other favorite part of this town is it is surrounded by olive groves and vineyards. Some of my most stunning views of the day were driving away from the town to head to Sienna.


The hilltop city of Sienna is absolutely stunning and a must see place if you are in Italy! The Old Town is full of medieval character and is listed as a heritage site by UNESCO. I started off my time here at the Piazza del Campo which is home to Siena’s classic Palio di Siena horse race, as well as stunning buildings like the Palazzo Pubblico and Torre del Mangia. I then ventured to the Siena Duomo which has incredible views from the top! I highly recommend buying a ticket to view the church and go to the Sky View at the top!

There is also great shopping in Sienna if you want to pick up a souvenir on your trip. I picked up a bottle of perfume from Note Del Chianti and LOVE it! Souvenirs like this are my favorite because now every time I spray on the perfume I think of the magical day I spent here!

How to Get To Siena:

  • You can take a train from Florence to Sienna which is about a hour and half long.
  • If you have car (like I did) make sure you figure out where to park before hand if you don’t want to be stressed when you arrive! The drive from Florence was only an hour, but I ended up driving around for another hour before I found a parking garage.

Overall I would highly recommend both of these places if you are taking a drive through Tuscany! Have you been to any other amazing places in Tuscany you would recommend?

Thanks for stopping by!


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