The Perfect Day Trip from Florence: 3 Cities in One Day

When you think of Tuscany, you probably think of lush rolling hills, wine-tasting, and its capital – Florence! This region in Central Italy has a wide range of landscapes from mountains and beaches to Chianti’s olive groves & vineyards. And of course, you can’t forget about the medieval towns scattered throughout the countryside or bigger cities like Pisa (yes, THAT Pisa with the Leaning Tower!). In this guide for the perfect day trip from Florence, you’ll not only get to see towns filled with history and culture but also taste test wines in Chianti hills!

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Tuscany Day Trip – Tour

Initially, my mom and I had so many places in Tuscany we wanted to visit that we had no idea how to figure out transportation or timing for each city. It’s safe to say it can get pretty overwhelming as taking the train everywhere can be pretty time consuming, so you may not be able to fit in as much as you think.

We eventually decided on this Tuscany 1-Day Sightseeing tour that would allow us to see 3 towns with a 3 course lunch & wine tasting in between. I think this option is great as you not only get a pretty detailed tour of some of the cities, but they also provide bus transportation between the towns. This is perfect for those that don’t want to deal with planning transportation and want to focus on exploring, like us! I would say the only downside is you don’t get a ton of time in each city since there is a pretty tight schedule to fit in all that they have planned. However, this trip does give a great preview into these different cities in case you do ever want to go back in the future!

Towns visited on this day trip from Florence include:

• Siena
• San Gimignano
• Pisa

Siena

Siena is a stunning medieval city that was once the center of commercial and banking activities. Surrounded by a 1,000 year old wall, this small town’s main square is even listed as a UNESCO World Heritage site. No cars are allowed here, so it’s the perfect place to stroll around and unpack all the history Siena holds. We also happened to visit on one of their market days! Stalls were set up around the outside of town and they were selling everything from fresh produce & meats to clothing. It was super cute, and I wish we could’ve stopped to buy ingredients to cook with! Anyways, here are some of the must see places in Siena:

Piazza del Campo

This piazza or “Il Campo” is the main town square. The seashell shaped square fans out from the Palazzo Pubblico which serves as the seat of Siena’s government. As you walk around Il Campo, be sure to admire the architecture of all the buildings lining the square. You can also see the Torre del Mangia, which was one of the tallest towers in medieval Italy.

• Palio – This famous horse race takes place twice a year in Il Campo (July 2 & August 16th)! It’ a really important tradition for the residents of Siena that takes place over 4 days. In this intense race, 10 horses are selected with each representing a specific area of the city also known as Contrade (17 contrade in total). You can read more about the race here!
  • Fun fact: There is a scene in the James Bond movie, Quantum of Solace, that is filmed in the middle of the Palio!

Duomo di Siena

Similar to other churches you’ll find in Europe, the architecture and elaborate designs that adorn the façade & interior of the Duomo are beautiful! The exterior is a mix of Gothic & Tuscan Romanesque style. Meanwhile, the interior is characterized by the black and white stripes running across the walls. There are also many valuable works of art by Donatello, Bernini, & Michelangelo that are worth seeing!

Monte dei Paschi

This is considered the oldest bank in the world in continuous operation, dating back to 1472.

Chianti Hills wine estate lunch

Our next stop was at an organic wine estate in Chianti Hills located between Florence & Siena. This region is famous for the Chianti Classico wine produced here! The emblem signifying Chianti Classico bottles is a black rooster and the wine must contain at least 80% Sangiovese grapes!

San Gimignano

Another famous Tuscan town, San Gimignano is most known for its skyline of medieval towers! You can think of it as the New York of medieval times! Of the 72 original tower houses in the town, only 14 remain today. These towers were used by families to display their wealth & power. For a full list of San Gimignano’s attractions, check their website! Places to visit:

• Piazza della Cisterna – This main square is lined with many small shops and restaurants
• Gelateria Dondoli – This gelateria was a past winner of the gelato world championship. They have unique flavors such as saffron with pine nuts & other seasonal specials!
• Palazzo Communale – Also known as Palazzo del Popolo (People’s Palace), this building is the seat of San Gimignano’s government. There’s also a museum featuring frescoes & other works of art!
• Torre Grossa – This is the tallest of the remaining towers. You can climb up for some great panoramic views of the countryside! Tickets are about 5 euros.

Pisa

Our last stop of our day trip was in Pisa! I didn’t really know what I expected of the area surrounding the tower; I always thought it was just a random tower in like the middle of a field hahah!

It was also crazy seeing the Leaning Tower in person after seeing pictures of it for so long. It’s hard to imagine the reality of a building leaning to that degree (4 degrees to be exact!) and still being able to stand until you’re in front of it.

I also learned that the Tower is actually the bell tower of the Pisa Cathedral located in Piazza dei Miracol! We ultimately decided to not climb the tower, but if you want to go to the top, you can buy tickets here. In this piazza you can find:

• Pisa Cathedral
• Baptistery
• Monumental Cemetery

Since it was our last stop after a long day, we were able to catch sunset. And let me tell you, this was probably one of the most beautiful sights of my whole Europe trip. The red hues cast on the white marble buildings are nothing short of breath-taking.