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.

You can’t really miss it—Florence’s cathedral (Cattedrale di Santa Maria del Fiore) dominates the skyline with that massive red-brick dome. Construction began in the 13th century and continued for nearly 150 years, which is evident in the diverse styles. The outside is covered in pink, green and white marble—oddly beautiful up close. Inside, check out Vasari’s Last Judgment fresco under the dome. If you’re up for the climb (and it is quite a climb), the view from the top is worth the leg burn.

The Fox Tucson Theatre, built in the 1930s, is on the National Register of Historic Places. The theater now screens movies, hosts concerts and serves as event space.