San Juan, Puerto Rico, Old San Juan
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Photo Credit: iStock.com / Doug_Rice | Cementerio de Santa María Magdalena de Pazzis
San Juan, Puerto Rico, colorful street
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Photo Credit: iStock.com / Maksymowicz | Colorful houses in Old San Juan
San Juan, Puerto Rico, Panama hats
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Photo Credit: iStock.com / Cameris | Ole Curiosidades
San Juan, Puerto Rico, Governor's Mansion in Fortaleza
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Photo Credit: Puerto Rico Tourism Company | La Fortaleza
San Juan, Puerto Rico, Castillo San Cristobal
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Photo Credit: San Juan NHS Collection | Castillo San Cristobal

San Juan, Puerto Rico

San Juan, Puerto Rico, Castillo San Felipe del Morro Photo credit: iStock.com / Aneese | Castillo San Felipe del Morro

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.

What We Love

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.

Best Known For

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.

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Who It's Best For

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).

Don't Say We Didn't Warn You

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.

Susan Moynihan

Susan Moynihan is a Florida-based contributor to ShermansCruise who has also written for Parenting and Woman’s Day.

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