Sure, Florence has world-famous art museums housing Renaissance masterpieces, medieval churches, incredible shopping, and plenty of amazing restaurants, but to truly understand Tuscany, you’ve got to get out of the capital and explore the countryside. Many villages are accessible by regional trains, but for the most autonomy, rent a car and map out a road trip through Tuscany’s rolling hills, stopping in these eight picturesque towns along the way.
Thirty miles south of Florence, the medieval city of Siena is a charming maze of narrow streets that all seem to lead to Piazza del Campo, the picturesque main square. Shaped like a semi-circle, the piazza has the air of a giant amphitheater lined with restaurants and bars where you can sit and watch the world go by. Be sure to visit the Romanesque Gothic Cathedral of Siena, which you can climb for spectacular views, and admire the medieval and renaissance art at the Museo Civico and Pinacoteca Nazionale di Siena. Book a room at the luxurious Grand Hotel Continental Siena, housed a historic palazzo filled with frescoes, chandeliers, and antiques.
Perched on a hill overlooking the valleys below, the rural village of Montaione is a quintessential Tuscan town. Here—where locals grow olives and press their own olive oil—farm-to-table isn’t a marketing gimmick but a way of life. Seek out Casa Masi, a rustic restaurant filled with antiques from the owner’s family that serves simple Tuscan cuisine, including homemade pasta presented in a hollowed-out wheel of cheese. The place to stay is Hotel Il Castelfalfi, a 2,700-acre estate that’s like a village unto itself. You can choose from the eco-friendly five-star hotel or rent one of the charming stone farmhouses and bring the whole family.
Pecorino di Pienza—a hard sheep’s milk cheese—is this hilltop town’s claim to fame. A UNESCO World Heritage site, it was commissioned by Pope Pius II in the 15th century as the ideal city, and wandering the narrow stone streets and piazzas, you might think it’s still a sort of utopia. John Voigtmann, a former Sony music exec, certainly did. He ditched the New York hustle and bustle to open La Bandita Countryhouse in the picturesque Val d’Orcia and then opened La Bandita Townhouse, a design-forward boutique hotel (and member of Design Hotels) with just 12 rooms, a farm-to-table restaurant, and an enviable record collection in town.
Most famous for its excellent Brunello di Montalcino wines, the hilltop town of Montalcino is the perfect place to enjoy a leisurely lunch after visiting one of the surrounding wineries. (Big names like Ruffino, Antinori, and Banfi all have estates here.) Head to Ristorante Enoteca Osticcio, a wine shop with a few tables in a small dining room with panoramic views of the Tuscan hills, for local specialties paired with a glass of one of the area’s signature reds. Stroll through the medieval streets and piazzas lined with shops selling everything from leather goods to local olive oil. Stay at Castello di Velona, known for its thermal spa and pool overlooking the scenic Val d’Orcia.
Tuscany’s not all rolling hills and vineyards—it also has a scenic coastline. Punta Ala is a great stopping point on this coastal region known as La Maremma. Unlike some of Italy’s most quintessential coastal towns, Punta Ala is virtually untouched, so instead of the pastel-hued houses clinging to the cliffs common in places like the Cinque Terre, you’ll simply find nature in all its glory. Rocky outcroppings, sandy beaches, and pine tree forests define this area, which Italians love to visit on vacation. Book a room at Baglioni Resort Cala del Porto, which grants guests access to a full-service beach club and the marina.
Lucca may not be as well-known as Florence, now but it was actually Tuscany’s capital until the late 10th century. This fortified city has retained its Renaissance ramparts and many churches, giving the impression of a place preserved in amber. The famed composer Giacomo Puccini was born here, and you can still hear his music during the annual festival dedicated to him, with concerts taking place every night from March through November. For a nice respite, check into Hotel Villa Casanova, an all-suite retreat in the countryside with an infinity pool and fantastic views of the city.
Pisa may be more famous for its leaning tower, but San Gimignano is known throughout Italy for its incredible collection of medieval towers. Out of the 72 towers that once existed, there are 14 still intact, and they create a skyline of medieval skyscrapers. Wandering through the city center—a UNESCO World Heritage site—feels like stepping back in time. After all, it’s one of the best preserved medieval towns in all of Italy. It’s easy to visit on a day trip from Florence or Siena, but if you want to stay overnight, Palazzo Buonacorsi Residenza d’Epoca is a good option.
Once an ancient Etruscan settlement, Volterra is known for its alabaster production. Wandering the city center, you’ll find lots of shops selling an array of bowls, serving platters, boxes, lamps, and other decorative items made with the luminous stone. It’s worth seeking out Rossi Alabastra d’Arte, an alabaster workshop open since 1912, where you can admire the models and machinery used to make incredible sculptures and buy a souvenir to take home. Volterra is also easy to visit as a day trip, but if you want to spend more time here, consider booking a room at Borgo Pignano.