SIENA

Siena’s principle sites cluster in the maze of narrow streets and alleys around the fan-shaped Piazza del Campo. One of Europe’s greatest medieval squares, the piazza sits at the hearth of the city’s 17 contrade, a series of parishes whose ancient rivalries are still acted out in the twice-yearly Palio. Once a capital to rival Florence, Siena is Italy’s prettiest medieval town, still endowed with the grandeur of the age in which it was at its peak (1260 to 1348).

PISA

For much of the middle ages, Pisa’s powerful navy ensured its dominance of the western Mediterranean. Trading links with Spain and north Africa in the 12th century brought vast mercantile wealth and formed the basis of a scientific and cultural revolution that is still reflected in Pisa’s spending buildings, especially the Duomo, Baptistry, and Campanile (Leaning Tower).

CORTONA

Cortona was founded by the Etruscans. Apart from being one of the oldest hill-towns in Tuscany, it is also one of the most scenic.

LUCCA

Lucca’s regular grid of streets still follows the pattern of the former Roman colony founded in 180 BCE. Giant, solid ramparts, built in the 16th to 17th centuries, help to shut out traffic, making the city a pleasant place to explore on foot. Lucca’s peaceful narrow lanes wind among the medieval buildings, opening suddenly to reveal churches, tiny piazzas, and many other reminders of the city’s long history, including a Roman amphitheatre.

MASSA MARITTIMA

Set in the Colline Metallifere (metal-bearing hills) where lead, copper, and silver ores were mined as early as Etruscan times, Massa Marittima is far from being a grimy industrial town. Excellent examples of Romanesque architecture survive from the period when the town became an independent republic (1225 to 1235).

MONTEPULCIANO

This is one of Tuscany’s highest hill towns, its walls and fortifications offering broad views over Umbria and Southern Tuscany. Its vineyards make the famous Vino Nobile wine.

MONTALCINO

Hilltop Montalcino sits at the hearth of vineyards that produce Brunello, one of Italy’s finest red wines.

MONTERIGGIONI

Monteriggioni is a gem of a medieval hilltop town. Built in 1203, 10 years later it became a garrison town. It is completely encircled by high walls with 14 heavily fortified towers built to guard the northern borders of Siena’s territory against invasion by the Florentine army.

SAN GIMIGNANO

The thirteen towers that dominate San Gimignano’s majestic skyline were built by noble families in the 12th and 13th centuries when the town’s geographical position (on the main pilgrim route from northern Europe to Rome) brought prosperity. The plague of 1348, and the diversion of the pilgrims route, led to the area’s decline as well as its current preservation. Today, although only one of the towers, the Torre Grossa, is open to the public, the town remains rich in works of art, good shops, and restaurants.

PITIGLIANO

Pitigliano is spectacularly situated high above the cave-riddled cliffs of the Lente Valley. Its maze of tiny medieval streets includes a small Jewish ghetto, formed in the 17th century by Jews fleeing from Catholic persecution.