When I’m staying somewhere and working, I love a day trip to keep things fun and adventurous. Outside of Florence I’ve found so many beautiful places to see that are just a quick car or train ride through the picturesque rolling hills. So grab your tickets or plug in the GPS—it’s time for a tour of Tuscany, Divine Living style!
Siena is a stunning medieval city where ancient tradition meets chic culture. Just an hour’s drive from Florence takes you to the city walls, where you can park and take a taxi in if driving (a rather high-quality and comfortable bus also leaves every hour).
The main town square, Piazza del Campo, is home to the world famous Palio horse race (an 800 year old tradition), and is also the perfect place to grab a slice of pizza, a glass of Vermentino, and sit and watch the day go by. I loved perusing the shops, both luxury and local, and even walked home with three $20 dollar capes that Sam will not be happy to find out about. Crowning the piazza is the Siena Cathedral. Built in 1380, it’s one of the most breathtaking old Duomos in the country. A few steps away, you can enjoy an unforgettable meal at the Antica Osteria Da Divo, a charming restaurant in the ancient rooms of an Etruscan cave. I highly recommend the pici pasta with the wild boar ragout. You may not enjoy it as well anywhere else from then on, but still—you’re welcome.
Few skylines can compare to that of San Gimignano, with its ancient towers rising up on a hill over the Tuscan countryside. Even with only 13 of an original 72 medieval skyscrapers remaining, few places in the world have preserved ancient urban architecture as well as this. After strolling around and visiting the chic shops, you might find yourself back at the central Piazza della Cisterna, enjoying the world-famous gelato from Dondoli.
If the sunset tempts you to linger over another glass of the local white Vernaccia wine, you might like to stay the night in an idyllic country castle at the nearby Borgo Pignano, or the chic L’Antico Pozzo in a 15th-century townhouse in the center of town. We’re not sure which is more romantic!
This trip takes you a little further out, about a 90-120 minute drive up to a rugged slice of coast along the Italian Riviera. Translating as “Five Lands,” Cinque Terre includes five idyllic Italian fishing villages dating back to the late Middle Ages. Cars were banned from the villages over a decade ago, so you’ll want to drive up to La Spezia and take the train in. The towns are connected by curving mountainside pathways, and by ferry, so it’s pretty easy to spend the day exploring the picturesque beaches and old cobblestone streets. Before long you’ll find yourself at an outdoor table overlooking the rocky cliffs, enjoying simply prepared and supremely fresh seafood.
This beachfront city is known as the Hamptons of Italy. It’s where the elite of Milan, Florence, and Genoa come to enjoy a glorious summer. Forte dei Marmi has plenty of style, but is more laid-back and old-world than say, glammed-out St. Tropez. The luxe beach clubs here offer an elegant way to relax, but you might also choose to explore the tree-lined streets on a retro bicycle, complete with a straw basket and leather saddle. However, with designer boutiques and chic cafes on nearly every street corner, prepare to make frequent stops.
Chianti is one of the biggest names in Tuscan wine and a classic destination for a day trip just 45 minutes outside of Florence. The best and simplest way to see the region is to book an all-inclusive high-end tour and get the full experience. Typically, a local wine expert and driver will take you out in a comfortable private car to visit three of the region’s best wineries. You’ll enjoy a beautiful Tuscan lunch with views of the rolling vineyards, and stroll through medieval towns like Castellini and Greve, where markets bustle with gourmet specialties. Often the tour guides will even facilitate getting bottles of olive oil and wine shipped straight to your door.