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 capital of Corsica and the birthplace of Napoléon Bonaparte, Ajaccio is an attractive seaside settlement with an animated yet slow-paced street life. Some of its primary attractions include the Maison Bonaparte (the Bonaparte family's ancestral home) and the fine arts museum Musée Fesch, containing works of great masters such as Titian and Botticelli.

Known around the world for its wine, Chianti is more than just a label—it’s a patchwork of rolling vineyards, olive groves, and old stone villages spread between Florence and Siena, with no clear delimitation. You’ll come across small family-run wineries, quiet roads, and landscapes that haven’t changed much in centuries. Even if you’re not deep into wine, it’s an easy and rewarding area to explore.