Tuscany

San Gimignano: Nicknamed the Manhattan of the Middle Ages, San Gimignano’s amazingly tall medieval towers are now a UNESCO World Heritage site. Its medieval architecture is a striking contrast to the large Renaissance influence across the region. If you happen to visit on a rainy day, the tight stone layout of the town takes on an evocatively eerie atmosphere. Fourteen gravity-defying tower houses stretch high above this fortified hilltop town, which itself looms over the surrounding idyllic countryside. It’s a great place to browse the photogenic local shops lining the narrow streets, visit the local torture museum, or sample local charcuterie, wines, and gelato. There’s even a museum of modern art for a taste of something much less gothic.
 

Pienza: Known as the “ideal city,” this is the main town of the Val d’Orcia (Orcia Valley), which is a UNESCO World Heritage site stretched across a large portion of southern Tuscany. For many, this valley is the iconic image of Tuscany, characterized by rolling cypress-covered hills and wineries. After driving through this stunning landscape, however, Pienza itself is no less impressive. Filled with soft sandstone-colored buildings, the town was designed according to Renaissance ideals of proportion and harmony in an attempt to create an entire living space that worked together, rather than a haphazard collection of individual buildings created for solitary functions. Many agree that it worked! Pienza is also famous for its locally produced pecorino cheese. They even have a pecorino festival (the Gioco del Cacio al Fuso), which is held the first weekend of September, in which locals compete by rolling large rounds of cheese at a target in the town’s main square.
 

Montepulciano: This town, world famous for its Vino Nobile di Montepulciano red wine, overlooks both the Val d’Orcia and the hills of Chianti. While the town is all about its famous namesake wine, it’s also a beautiful example of a medieval hill town. But it’s just one of several similar towns in the Chianti region, including Radda, Greve, Montefioralle, and Montalcino, that are well worth a visit.
 

Lucca: This Tuscan city has the best-preserved Renaissance city walls in all of Italy. While other cities in the region often pulled down their walls to accommodate increased populations and modernization, Lucca instead incorporated them into its growth. Today, the walls (which are over 30 feet high and 60 feet thick) have been transformed into an elevated park that runs over two miles around the town. Within the walls, the town retains its Renaissance character. The city’s main square is in the shape of an oval, as its boundaries traced the foundations of the old Roman amphitheater. There are also several surviving towers within the town that you can visit, including one with a small grove of trees growing on top!
 

Volterra: Alabaster rules in Volterra, and the ancient tradition of carving this delicate stone into exquisite works of art or everyday objects dates back to Etruscan times. Volterra was, in fact, one of the main towns settled by the Etruscans centuries before the Romans ruled the Italian peninsula, with the city’s walls dating back to the 4th Century B.C.E. Throughout the town, there are well-preserved ruins of ancient temples and an amphitheater, as well as an enormous fortress built by the Medici dynasty after they took control of the city in the 15th Century.
 

Elba: The largest of the Tuscan Islands, Elba is an hour ferry ride from the Italian coast (there is also a small airport). Famous as the island from which Napoleon Bonaparte escape his first exile, it has a certain draw for history buffs. The island’s capital, Portoferraio, boasts an impressive fort and two villas used by the infamous dictator. But it’s the island’s natural beauty, stunning blue waters, miles of hiking and biking trails, and relative distance from the main tourist track that make it a must-visit for anyone.