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 pageantry, Palio horse race, and a stunning traffic-free main square — great anytime but best after dark.
▲▲ Pisa A city more famous for its iconic Leaning Tower than for its other equally impressive monuments on the gleaming white Field of Miracles.
▲▲ Lucca Charming city with a lively (and flat) town center, ringed by intact old walls wide enough for biking and strolling.
▲▲ Volterra Just far enough off the beaten path, surrounded by thick walls and hilly scenery, with a long Etruscan history and unusually interesting sightseeing for a small town.
▲▲ Montepulciano Rugged town crowning a ridge, with dreamy vistas of the countryside and wine-tasting in inviting cantinas.
▲ San Gimignano Epitome of a hill town, spiked with medieval towers offering superb views, popular with tourists who crowd the narrow alleys by day.
▲ Montalcino Wine-lovers’ paradise boasting a dramatic 14th-century castle, encircled by olive groves and famous vineyards.
Pienza Tiny Renaissance-planned architectural gem of a town nestled in a scenic hilly landscape.
Cortona Hillside town under the Tuscan sun, with historic churches and museums featuring Etruscan and Renaissance artifacts and art.