• Montepulciano, Italy

Tuscan Hill Towns

The sun-soaked hill towns of central Italy offer what to many is the quintessential Italian experience: sun-dried tomatoes, homemade pasta, wispy cypress-lined driveways following desolate ridges to fortified 16th-century farmhouses, atmospheric enoteche serving famously tasty wines, and dusty old-timers warming the same bench day after day while soccer balls buzz around them like innocuous flies. Hill towns are best enjoyed by adapting to the pace of the countryside. So, slow…down…and savor the delights that this region offers.

At a Glance

▲▲▲ Siena Red-brick hilltop city known for its medieval pageantry, Palio horse race, proud spirit, and a 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.

▲▲ 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.