Roadtrip to Tuscany

The Medieval cities of Siena, San Gimignano and Montepulciano

Think of Tuscany and a few signature sights come to mind: the iconic Cypress tree, miles of vineyards, and quaint medieval villages untouched by the 21st century. Travel a couple of hours outside of the bustling artist city of Florence, and find yourself right in the middle of a green paradise. It's wine country, but even if you don't come there for a glass, Tuscany has other riches beneath its arches and behind its walls. When I stayed in Florence, Tuscany was definitely on my list for a day trip. Through my hotel, I was able to arrange a private driver to three medieval towns—Siena, San Gimignano and Montepulciano. My driver, Alessandro, was knowledgable and quite funny on the trip, and we stopped frequently to take photos and to breathe in the fresh country air. After the trip, in typical Italian hospitality, Alessandro told his son Alessio to give my family a free bottle of wine at the restaurant where he worked. He said, "This family is my friend!" The Italian way of life is just as beautiful as the duomos, the pizza, and the souvenirs. Here are some of my favorite parts of these ancient cities.


Miemo Penttinen

Siena is one of the most popular places to visit in Tuscany, known for history and art spread throughout its 17 districts, or "contrade." It was founded by the son of of Remus, one of the founders of Rome, so discovering great cities ran in the family. The first thing you'll notice about Siena is the enormous red building known as the Palazzo Pubblico, or the civic palace. Beside it is a staggering tower called the Torre del Mangia. The Palio is an exhilarating horse race run twice a summer. There, you'll definitely want to see the Fonte Gaia, which is a copy of an original fountain decked out with Jacopo della Quercia sculptures. Talk about a feast for the eyes! You'll also want to get an OPASi Pass to visit the Duomo, then take a trip to one of Europe's oldest hospitals, Santa Maria Della Scala.

San Gimignano

Stig Stockholm Pedersen

If you couldn't get enough of Siena's Torre del Mangia, San Gimignano has even more towers. In fact, it's known as the "city of beautiful towers." Back in the day, there used to be 72, but now only 14 remain. You can imagine how much this city has been through. Relish in the rich history of its13th century walls and the town centers on the Piazza della Cisterna. Take in the Duomo di San Gimignano, which is a 12th century church bedazzled in Ghirlandaio frescoes. But the coolest part of San Gimignano is the myth behind the Devil's Tower. According to legend, when he left town one day, the tower's owner noticed that the tower appeared taller than it was before! Creepy! But one of my favorites was the Cugnanesi Tower, which was the tallest in San Gimignano.


Tomas Zrna

If you're into wine, you'll definitely know the two that come from the Val di Chiana and the Val d'Orcia of Tuscany: the Vino Nobile di Montepulciano and the Rosso di Montepulciano. But not only can you feel free to knock back a glass or two, but also enjoy the stunning castle of Montepulciano, the Piazza Grande, and the Bravio delle Botti contest (which is a barrel-racing contest every August—the Italians love their sports!). Go through the gate of the Porta al Prato and visit quaint shops in the Corso. And if you're in the mood for some more churches, check out Santa Maria dei Servi and San Biagio. You'll feel like you stepped back in time!

When you're ready for a day off from the narrow streets and mopeds whizzing by in Florence, I highly recommend a road trip to Tuscany. You might just get a free bottle of wine!


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