San Gimignano: The "Medieval Manhattan" bristles with more than a dozen tall stone towers, all slightly askew. It wins the "Most Densely Decorated Church" award for its old Duomo, whose interior walls are slathered with 15th-century frescoes. San Gimignano's skyline and back alleys, especially when moonlit, make it one of Italy's most romantic hill towns. Stay until all the tour buses have left, when you'll have the gardens and small piazze all to yourself.
Volterra: Proud Volterra has been important in western Tuscany since the Etruscan Age. From its magnificent rocky promontory, the city surveys the sometimes wild, vast countryside surrounding it. Volterra is full of workshops where artisans craft the native alabaster into translucent souvenirs. And from a windswept terrace road you can look over some of Tuscany's best-preserved Roman ruins.
Montalcino: Impressive from a distance with its broken-toothed fortress on a high hill, Montalcino turns out to be surprisingly tiny when you get close. It has a few sights and churches and a good small museum, but what you really come for is to sip the town's beefy Brunello wine, take a passeggiata with the locals in the evening, and watch the shadows fill the valley far below your hotel window as the sun goes down.
Montepulciano: Although Montepulciano has medieval side streets galore, its main attractions are the deep red Vino Nobile wine and one of Italy's finest centrally planned Renaissance temples, a church set in its own little green park below the ancient walls of the town.
Cortona: This stony hill town is no longer big enough to fill its medieval walls, but it still has its museums of paintings by Fra' Angelico and local boys Luca Signorelli and Pietro da Cortona. The restaurants serve steak from the famed Chiana cattle, raised in the valley below, where Etruscan tombs hint at the city's importance in a pre-Caesar Tuscany.
Gubbio: This ancient Umbrian stronghold and renowned ceramics center is like the last outpost of civilization before the wilderness of the high Apennines. The central piazza cantilevers over the lower town like a huge terrace. The square is bounded on one end by a mighty palace, all sharp stone lines and squared-off battlements. Inside is a cluttered archaeological museum and the same echoey medieval atmosphere that pervades the entire town. Gubbio is unique among hill towns -- an antique center unto itself, to which surprisingly few visitors venture.
Todi: When they were handing out quaintness to Italian hill towns, Todi took far more than its share. Many of its streets are so steep they've been chipped with shallow staircases down the middle. Vistas across the valley open up unexpectedly, and on the perfectly medieval main piazza is a town hall sprouting a staircase perfect for an Errol Flynn sword-fight scene. The church on the outskirts of town is perhaps Italy's most beautiful High Renaissance construction.
Note: This information was accurate when it was published, but can change without
notice. Please be sure to confirm all rates and details directly with the companies in question before
planning your trip.
