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.

The entrance to the park is a short walk along Castle Street, to the left of the castle. The gardens have their own walled parapet that features incredibly life-like stone animals including a bear, lion, hyena, monkeys and a pelican. The park runs alongside the River Taff and has great views of the castle and its moat – it even has a miniature Stonehenge!

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.