My absolute favorite part of visiting Florence was the day I spent exploring Tuscany. I could have spent 2 weeks going from town to town, trying wine and eating pasta in the Chianti region. But if all you have is a day, there are many tours from Florence that can help you live out your Under the Tuscan Sun fantasy before departing Italy.
In about 10 hours, you can visit the medieval towns of San Gimignano & Monteriggioni, have lunch and taste wine in the Chianti region, and tour historical Siena. Keep reading to learn more!
San Gimignano
Start the morning in San Gimignano about 45 minutes outside of Florence. It is one of the most well preserved medieval villages in Europe. It is known for Towers of San Gimignano, many of which have been destroyed by war. According to our tour guide, now only 7 of these towers stand.
As you stroll along the cobblestone streets, you can shop for leather goods, boar sausage, handmade pasta, and chianti in the many shops. You may also want to stop for an espresso to sip and start your day.
In the first of the two squares, you have to stop at Gelateria Dondoli, winner of the gelato world championship. Even though it was morning, I decided to get gelato for breakfast, because why not?! You’re on vacation. While you eat your gelato, check out the many viewpoints around the city to gaze upon Tuscany as the morning mist clears off the hills.
Monteriggioni
Your next stop is Monteriggioni about a 30 minute drive from San Gimignano. Monteriggioni was built in 1214, and while not as well maintained as San Gimignano, is still a lovely place to glance into what medieval Italy would have been like. For 5 euros, you can walk the city walls for a beautiful view of Tuscany.
You may also see pilgrims in the city as it is a stop on the Via Francigena, or the Camino to Rome. This pilgrimage historically started in Canterbury, England and crosses though France, Switzerland, and finally to Rome.
Lunch in a Tuscan winery
Now that you’ve worked up an appetite from all that walking, it’s time for pasta and wine! Yay! As I learned from our tour guide, Italians typically have pasta for lunch, and pizza is for dinner on the weekends. So in the Italian style, we were served penne with a delicious red meat sauce for lunch.
But before lunch it was time for wine! The tasting started with a crisp dry Prosecco (they also had a sweeter wine for those who wanted it). The Prosecco was followed by a Chianti, Chianti Classico, a Super Tuscan, and an extremely strong dessert wine (I had so much wine at this point, I don’t know what it was, but it was boozy!). As a red wine lover, I was in heaven.
I highly suggest bringing a suitcase with extra room to Tuscany so you can bring chianti home! It is so much cheaper than wine in the United States (especially Northern California) and is just as good, if not better. It’s better.
Siena
Your last stop is Siena! As with the rest of the Tuscany, I could’ve spent days here. It such a unique city with rich history, so I definitely recommend taking a tour of the city with a local guide.
Contradas & the Palio di Siena
Siena is split into 17 different neighborhoods, or contradas, that compete in a horse race every year called the Palio. Each neighborhood has its own symbols and mascots that can be found on flags, statues, and lamp posts throughout the neighborhoods. It’s fun to walk through the city and try to determine when the neighborhood changes.
If you are lucky enough to be in Siena in the summer, you may get to catch the twice yearly Palio the Piazza del Campo. It occurs on July 2nd and August 16th every year. Each neighborhood has a horse compete in the race, pretty much to win bragging rights. As I visited Siena in August I got to see the July winner’s flag hung in the Piazza!
Duomo di Siena
After visiting the Piazza del Campo, make sure to stop in the Siena Cathedral. This cathedral is unique because of the amazing floors. The entire floor is covered in 56 gorgeous marble mosaic panels, which contain art representing the contradas of Siena. I have never been this fascinated by a floor! Even if you are not into art or museums, it is definitely worth a 20-30 minute stop.
Many day tours will offer the option to add on the Cathedral entrance fee and tour, but you can also just buy a ticket and visit the cathedral on your own.
Tip: Like all churches in Italy, modest dress is required (no shorts & shoulders must be covered).
As you leave Siena, make sure to take a photo of the city from outside the gates. There are some great view points near the Basilica of San Domenico.
After Siena, you will make the hour long trip back to Florence to rest after your fun filled day. I’m sure this one day trip will make you fall in love with Tuscany and start planning your return trip right away!
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