Best weather: May, September, and October. July and August are hottest and most humid. Tourism swells from May through September.
What To Do
Indulge in Amazing Cuisine: When you come to Tuscany, leave your watch at home. This region inspires contemplation, exploration, and lingering picnics featuring some of Europe's best food and wine. Take advantage of local specialties: olive oil, mushrooms such as porcini and truffles, roasted meats and salami, sheep's milk cheeses such as pecorino and ricotta, and wine (don't miss the wine estates and castles of the Chianti Classico region in central Tuscany).
Where To Go
Siena: A must-see on any Tuscan tour, this charming sienna-hued city in central Tuscany is one of Italy's best-preserved medieval towns. Siena was a hotbed of art and learning during the Middle Ages, and its hilly streets, Gothic cathedrals, and stone palaces are perfect for daydreaming. The Piazza del Campo -- a large square with 11 streets snaking into it -- lies at the city's heart. San Gimignano: Originally called the City of the Beautiful Towers, this wonderful medieval town near Siena is noted for its towers -- 14 of the more than 75 spires that once defined its skyline remain. Visit small art galleries, shops, restaurants, and the dreamy 12th-century Romanesque Collegiate church, with walls covered in frescoes and a blue vaulted ceiling speckled with golden stars. Pisa: This town in western Tuscany is known for its leaning tower, but don’t forget to visit the Campo dei Miracoli, which includes a stunning trio: the Battistero (Baptistery), Camposanta (cemetery filled with earth brought from the Holy Land by crusaders), and Duomo (cathedral). The lamp suspended over the cathedral's pulpit is called Galileo's Lamp and is said to have inspired his theories on pendulum motion. Volterra: Volterra, perched on a high plateau in western Tuscany, offers stunning vistas of the surrounding countryside and is known for the beautiful statues its craftsmen create from locally mined white alabaster. The Museo Etrusco Guarnacci owns one of the best collections of Etruscan artifacts in Italy, including 600 intricately carved funeral urns. Lucca: Exploring this city in northern Tuscany is a delight. Scamper between the columns of grand Romanesque churches, mingle with locals at an outdoor market in the Piazza del Mercato, and stroll the wonderful gardens of nearby Villa Reale (Royal Villa), once the home of Napoleon's sister (closed December to February). A music festival is held in the villa's Teatro di Verdura, a theater created with topiaries, during July and August. Arezzo: This city in eastern Tuscany is one of Italy's three major gold jewelry production centers. Here you'll find stunning frescoes (don't miss the collection at the 13th-century church of San Francesco), richly colored stained glass, and Etruscan pottery. Browse antique shops around the Piazza Grande for deals, or visit the open-air antiques fair held the first weekend of every month.
Cortona: Cortona's steep streets, slender alleys, and ancient buildings have an eclectic charm. The medieval hilltop town is best known for its small museums, churches, and fine antique shops. Trek up the garden-lined Via Crucis to the church of Santa Margherita for excellent views.