For COVID-19 Travel and RS Tours information, see our FAQ.

  • 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 pageantry, Palio horse race, and a stunning traffic-free main square — great anytime but best after dark. It's also a fine home base for exploring the Tuscan countryside with a driving tour of the Crete Senesi.

▲▲▲ Montepulciano Rugged town crowning a ridge, with dreamy vistas of the countryside and wine-tasting in inviting cantinas.

▲​▲ Montalcino Wine-lovers’ paradise boasting a dramatic 14th-century castle, encircled by olive groves and famous vineyards.

▲▲ 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.

▲▲ Pienza Tiny Renaissance-planned architectural gem of a town nestled in a scenic hilly landscape.

▲​ San Gimignano Epitome of a hill town, spiked with medieval towers offering superb views, popular with tourists who crowd the narrow alleys by day.

Cortona Hillside town under the Tuscan sun, with historic churches and museums featuring Etruscan and Renaissance artifacts and art.