The Best Day Trips from Florence, Italy

As the birthplace of the Renaissance, Florence has plenty of art, history, and culture to keep you busy. But just outside the city, you’ll find award-winning vineyards, medieval hilltop towns, and a culinary capital unlike any other in Italy. Here, the best day trips from Florence, Italy—all just an easy train-ride away.

Siena

For centuries, Florence and Siena have been rival cities, competing to have the most impressive art, architecture, and acclaim. The entire town of Siena is a UNESCO World Heritage Site due to its medieval foundations, many of which can still be seen today. Start your day off at the iconic cathedral—a striking marble structure that showcases sculptures by Pisano, Donatello, and Michelangelo—followed by a walking tour through the city’s 17 contrade (districts), which fan out from the central Piazza del Campo. The piazza is the spirit of Siena; it is home to the ancient palace (Palazzo Pubblico), the Gothic town hall, and Torre del Mangia, a slim 14th-century tower that visitors can still climb today. For a true adventure, plan your trip around Palio, a historic horse race that takes over the main square twice every summer. Jockeys dress in medieval garb to represent the 17 contrade and ride bareback to win for their wards. The craziest part: there are no rules to the race, meaning the crowds and jockeys often get rowdy

Bologna

Let’s be real—the main reason to visit Italy is to eat your face off. Foodies should hop the train an hour north to Bologna, the capital of the Emilia-Romagna region and one of the biggest culinary destinations in the country. Bologna is the birthplace of Italy’s most iconic staples: prosciutto di parma, parmigiano-reggiano cheese, tortelli pasta, and balsamic vinegar. Try them all for yourself at the new FICO Eataly World. This million-square-foot food palace features cooking classes, rotating gastronomic exhibits, and six multimedia centers—not to mention the 40+ trattorias and stands, including a panettone bakery, a mortadella bar, and an enoteca that serves 100 Italian wines by the glass. Now that’s la dolce vita.

San Gimignano

When you imagine the romantic, hilltop towns of Tuscany, San Gimignano is one of the first to come to mind. From the narrow side-streets to the charming gelaterias, it has all the trappings of a bucolic Italian getaway. Yet, it’s also a haven for history buffs: more than 72 medieval towers once decorated its skyline, and today 14 of those still exist, giving the town the nickname Medieval Manhattan. Climb 200 feet to the top of the bell tower for sweeping views of the countryside, vineyards, and olive groves before wandering down to the preserved city center for a step back in time.

Pisa

Yes, Pisa may be touristy, but there’s much more to do besides posing next to the Leaning Tower. Beat the crowds by starting the morning early at the 22-acre Piazza dei Miracoli; snap a picture of the tower but spend more time exploring the massive 11th-century cathedral and baptistery. Then, leave the compound to check out the Palazzo Blu’s rotating art exhibits (right now you can see surrealist works by Duchamp), or find some of the city’s best street art, including the colorful Tuttomondo mural by Keith Haring. In the afternoon, relax on a bench in the green Scotto Garden and listen to a local open-air concert. Throughout the summer, the garden also hosts outdoor movie nights for families.

Chianti

Chianti is one of the most famous wine regions in all of Tuscany, and luckily, it’s right on Florence’s doorstep. Just 45 minutes south of the city, the landscape changes to rolling vineyards, charming villas, and lush, forested valleys. Rent a car and cruise around the countryside, stopping at wineries like Antinori nel Chianti Classico. The Antinori are a Florentine family that have been making wine since 1385, and have passed the business through 26 generations. The vineyard is centered around a large, contemporary complex that houses site-specific installations, a museum of the family’s historic art collection, a theater, and a gorgeous terra cotta cellar. Save time (and room) for lunch out on the restaurant terrace, where you can sip Sangiovese and tuck into a plate of tagliolini pasta with white truffles.

Prato

Florence may be the heart of the Renaissance—but Prato is the capital of modern art. Museo del Tessuto is the largest textile museum in Italy and a tribute to Prato, a city that has lead the textile industry since the Middle Ages. Here, you’ll see more than 600 fabrics, tapestries, and embroidered fashions dating back to the 13th century as well as modern sketches and designs. However, the crown jewel is Centro Pecci; after a 10-year renovation, the contemporary art museum reopened in 2016 with double the exhibition space, a library, an outdoor theater, a cinema, a bookshop, and a restaurant. Now, it showcases a collection of 1,000 works by avante garde artists like Andy Warhol, Anish Kapoor, and Jan Fabre. This year, it’s celebrating its 30th anniversary, so make sure to check out the line-up of special performances, talks, and installations as well as the new bistro bar. For those wanting more traditional art and frescos, head to the Palazzo Pretorio Museum, housed in a castle with a panoramic rooftop terrace.