A north-to-south look at Tuscany’s cities and provinces.


Along with its famous oval-shaped Piazza dell’Anfiteatro, the walled city of Lucca has a network of sleepy alleyways—perfect for exploring by bicycle. This August, the city holds an opera festival, in honor of the 150th birthday of the city’s most legendary resident, Giacomo Puccini.


The 120-square-mile region of Chianti, which extends from Florence all the way down to Siena, is renowned for its namesake wine. Take time to visit the cobblestoned towns of Greve, Radda, and Strada to sample pasta with cinghiale.


Ancient historian Livy once lauded Arezzo for holding its own as a key Etruscan city. Today, the city still retains a unique identity, with antiques markets (Art Deco jewelry, carriage clocks), stylish boutiques, and intimate restaurants.


Pisa’s main draw used to be its gravity-defying tower. Now, the city is one of the best entryways to Tuscany, thanks to Delta’s new nonstop flight from New York.


Artisan workshops line the streets of Volterra, a hilltop Etruscan village in the province of Pisa. Keen-eyed collectors will find contemporary alabaster sculptures among the hordes of kitschy sculpted angels, Grecian urns, and swooping eagles.


Maremma is still the region’s wildest area, with shrub-covered hillsides and unspoiled coastline. The terrain is changing, though, as high-wattage resorts such as Alain Ducasse’s L’Andana (andana.it) move in.


Siena might seem defined by its past—medieval brick palazzi, winding streets, and, of course, the 350-year-old Palio horse race—but the city is gaining momentum as a modern destination, thanks to the arrival of several new hotels, including the Grand Hotel Continental (ghcs.it) and Campo Regio Relais (camporegio.com).