With its manicured fields, rustic farms, cypress-lined driveways, and towns clinging to nearly every hill, Tuscany is our romantic image of village Italy. Venture beyond the fringes of Florence and you'll find a series of sun- and wine-soaked villages, each with its own appeal. Stretching from the Umbrian border to the Ligurian Sea, the landscape changes from pastoral (Crete Senesi) to rocky (Chianti) to mountainous (the Montagnola) to flat and brushed with sea breezes (Pisa).
At a Glance
▲▲▲ Florence Art-packed, bustling city — starring Michelangelo's David, Renaissance paintings, and Brunelleschi's dome — with Ponte Vecchio spanning the flood-prone Arno River.
▲▲▲ Siena Red-brick hilltop city known for its medieval pageantry, Palio horse race, proud spirit, and stunning traffic-free main square — great anytime but best after dark. Also a fine jumping-off point for exploring the Tuscan countryside with a driving tour of the Crete Senesi region.
▲▲ Pisa City more famous for its iconic Leaning Tower than for its other equally impressive monuments on the gleaming Field of Miracles, and with an old town that's fun to wander and delightfully tourist-free.
▲▲ Lucca Charming town with a lively (and flat) center full of pleasant cafés and shops, ringed by intact Renaissance walls wide enough for biking and strolling.
▲▲ Volterra Authentic, walled hill town just far enough off the beaten path, with a long Etruscan heritage that makes for unusually interesting sightseeing for such a small town.
▲▲ Montepulciano Rugged town crowning a ridge, with dreamy vistas of the countryside and wine-tasting in inviting cantinas; makes a good home base for drivers.
▲ San Gimignano Epitome of a hill town, spiked with 14 medieval towers offering superb views; popular with tourists who crowd the narrow alleys by day and an evocative delight by night.
▲ Montalcino Wine-lovers' paradise boasting a dramatic 14th-century castle, encircled by olive groves and famous vineyards (and a manageable home base for nondrivers).
▲ Pienza Pint-sized Renaissance-planned architectural gem of a town nestled in a scenic hilly landscape.
▲ Cortona Hillside town basking under the Tuscan sun, with historic churches and museums featuring Etruscan and Renaissance artifacts and art; easy stop for drivers heading to or from neighboring Umbria.
▲ Elba Small island an hour's ferry ride from the mainland, with a ruggedly mountainous landscape and twisty drives to inviting beach towns.