WHAT TO KNOW

Perched on the eastern border of Toscana, Cortona is one of the oldest towns in central Italy. In fact, according to one creation legend, the hilltop was first inhabited by none other than Noah after the Great Flood. Look around for signs of the many chapters of Cortona’s history, from ancient Etruscan walls to steep medieval staircases to romantic Renaissance cathedrals.

WHERE TO GO

Start in the heart of Cortona, La Piazza della Repubblica. Day or night, the historic square is bustling with locals and visitors, drinking morning coffee or having an evening aperitivo. From there, wander up and down the twisted streets: each turn will offer a new marvel. Don’t miss the Museo dell’Accademia Etrusca, a museum with artifacts ranging from the Etruscans to the Romans; Piazza Garbaldi, which has an especially incredible view of the surrounding countryside; and Santa Maria Nuova, a beautiful domed cathedral. Don’t forget to pop in the boutiques along the way!

WHAT TO TASTE

Cortona is located in Valdichiana, or the Chiana Valley, an especially fertile area in Toscana – the perfect conditions for food and wine! The town’s trattorie offer typical Tuscan fare: rustic and simple, with an emphasis on local ingredients. Cortona is especially known for its Sagra della Bistecca, a two-day food festival held each August to celebrate the local Chianina cattle, followed by the Sagra del Fungo Porcini, a similar festival focusing on porcini mushrooms. Even if you miss these sagre, be sure to enjoy these local specialties while you’re there!

Tracing back to the Etruscans, winemaking is an ancient tradition in Cortona. The region has a DOC certification, guaranteeing excellent local white, red, and dessert wines, produced according to strict standards. For a traditional taste of Cortona, finish dinner with a glass of sweet Vin Santo – don’t forget to dip the cantucci!