San Gimignano

Many coastal-bound visitors kick off their itineraries in this hilltop town, a little less than an hour’s drive northwest of Siena, whose medieval towers and walls have been beautifully preserved. Spend the morning marveling at the city’s fourteen remaining towers, among Tuscany’s main architectural attractions and a UNESCO World Heritage site. You’ll probably be coping with lots of tours, so plan your day for efficiency. Park the car outside the walls and go directly to the Piazza del Duomo for an up-close look at seven of the towers, including Torre Grossa—at 177 feet high, the tallest of the fourteen—which you can climb for an exceptional view.

Next visit the 11th-century Duomo (known as la collegiata) to see the wall-length 14th-century frescoes of Christ and the Chapel of Santa Fina, whose murals show San Gimignano as it was in the 1400s. If you have time, add in the Church of Sant’Agostino, well worth a visit for the seventeen-panel fresco The Life of Saint Augustine, surrounding its high altar and chapel. Shopping options are limited, but Leoncini (Via San Giovanni 60-64) carries hand-painted Italian pottery and tableware that can be easily shipped home. In June, the annual Ferie delle Messi turns the Piazza del Duomo into a jousting arena filled with knights, jugglers and locals in 14th-century costumes. San Gimignano’s market day is Thursday.

Indagare Tip: A San Gimignano combined-entry ticket includes access to Torre Grossa and the Chapel of Santa Fina, as well as to the Civic and Archeological Museums, the former of which contains artworks by Benozzo Gozzoli, Filippino Lippi, Pinturicchio and Lippo Memmi.