• 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 atmospheric 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 era. From its magnificent rocky promontory, the ocher city surveys the sometimes wild, vast countryside surrounding it. Volterra is full of workshops where artisans craft the native alabaster into translucent souvenirs.
  • 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 Chianina 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 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.
  • Todi: Umbria's most picturesque hill town somehow avoids most of the tourists. 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 proportioned medieval main piazza is a town hall sprouting a staircase perfect for an Errol Flynn sword-fight scene.

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.