Escaping to San Juan's Condado

street party The San Sebastian Street Festival is hands down the biggest annual event in San Juan, and no doubt the most exciting: ‘round-the-clock revelry spread out over four days each January, bringing together art, music, food and drink while celebrating the end of Puerto Rico’s holiday season.

Visitors leave the rental car behind and take a bus—tons of them are dispatched for this event. Residents of Condado and nearby Miramar have been known to hoof if to Old San Juan in their comfiest of old sneakers, joining the throngs walking past the Caribe Hilton, Escambron Beach and the San Cristobal Fort. The kick-off ceremony on Thursday is especially fun, with stilt walkers and cabezudos and their huge papier-mache heads officially opening the fiestas.

During the day, the Cuartel de Ballaja, which once served as barracks for Spanish troops, is filled with artists selling their crafts—everything from homemade candy to one-of-a-kind paintings. The hottest item—sold along San Sebastian Street—is the official festival poster, prepared each year by a carefully chosen artist. With bands playing local rhythms and many dancing away well into the night, you’ll have to mentally prepare yourself for thousands of people around you, but won’t soon forget the atmosphere of unadulterated fun. The unofficial dates for the next festival are Jan. 19-22; confirm with the Puerto Rico Tourism Company prior to making travel arrangements.