The gateway to the Caribbean, San Juan is a lively mix of culture and style, from the narrow alleys of Old San Juan to the lively nightclubs of Condado. Dig into local dishes like mofongo (fried mashed plantains) and chicharrones (pork rinds), shake your hips to salsa and reggaeton, and hit the tawny beaches that extend out east and west.
Nightlife: The resort strip along Condado and Isla Verde is filled with restaurants and clubs, many featuring big bands and packed dance floors. Dress the part: There's no such thing as casual Friday here, especially after the sun goes down.
Shopping: Yes, there are a lot of tchotchkes in the shops; this is a cruise port, after all. But there are also gems to be found. Ole Curiosidades on Fortaleza Street sells handmade Panama hats, while Galeria Botello showcases paintings and antique, carved saints.
Old San Juan: The historic part of the city charms with cobblestone streets and shady courtyards housing cafes and galleries. Pop into Barrachina for a pina colada, invented here in 1963.
Castillo San Felipe del Morro: The 16th-century fort, now a World Heritage Site and National Historic Site, overlooks the sea and is backed by a wide green that draws sunbathers, Frisbee players, and picnickers.
History Buffs: Set in the heart of the historic district, the 1540 Cathedral of San Juan Bautista is the second oldest cathedral in the Americas. Across the street is El Convento, a monastery-turned-hotel where you can enjoy great tapas while overlooking the inner courtyard.
Foodies: Puerto Rican cuisine draws from Spain, Latin America, Africa, and the Caribbean. Experience it in high form at Pikayo, or more casually from street vendors selling grilled pinchos (kebabs) or bacalaitos (cod fritters).
There's a Language Barrier: Puerto Rico is a U.S. territory, but it has a culture all its own. English and Spanish share the title of "official language," but Spanish is much more widely spoken, especially outside the city.