Thanks to the semiannual Palio, Siena shares a reputation with Spain’s Pamplona for being crazy two days of the year and asleep the other 363. That’s really not a fair rep, though, because the Sienese provide plenty to see even when they aren’t racing bareback around Il Campo. Take the steep pedestrian-only streets of Siena’s centro, for example. The completely befuddling medieval layout is Tuscany taken to its illogical—and charming—extreme. Amid the frozen-in-time Gothic architecture, Siena is also a respectable university town with a campus indistinguishable from the city around it; you’ll only realize you’re at the university when you poke into a church and discover it’s actually the Linguistics Department. With quirky nightlife, relative freedom from the overwhelming Florentine tourist crowds, and a maze of streets hiding secrets you could spend months trying to unlock, Siena is worth an extended stay.