Tucked into the hillside just outside Cortona, Le Celle is a small Franciscan hermitage dating back to the 13th century. It’s peaceful, simple, and still run by monks today. Saint Francis stayed here briefly, and you can actually see his old cell. The hermitage is a sight in itself, but also benefits from beautiful surroundings.

Siena still runs on medieval time—in the best way. Its centre hasn’t changed much in centuries, and that’s part of the charm. The Piazza del Campo is the heart of it all—it’s where the Palio horse race happens twice a year. Climb the Torre del Mangia for wide views across the rooftops. The cathedral’s worth the time, especially its black-and-white striped interior, detailed floor mosaics (open seasonally), and the Piccolomini Library tucked inside. Don’t skip the crypt or the Museo dell’Opera del Duomo—they’re quieter and give you a different angle on the city.

During the summer outdoor seating in the garden. For menu see website.

This is one of the oldest churches in Italy – dating from the 5th century AD. Strange symbols and references to the Knights Templar can be seen, as well as the symbol of the pentagram near the church entrance. This is a must-see.