Hotel · San Juan
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"Michael Simeone, an architect, and his husband Matthew McGregor, a lawyer, live in Brooklyn, NY. They got married at El Convento in Puerto Rico in March 2018."
This eclectic, art-filled 1700s inn in Old San Juan boasts tropical gardens, exotic birds, ocean views, and a rooftop terrace for true local vibes.
3 Postcards
Resort hotel · San Juan
Nestled between the trendy Condado and historical Old San Juan, the Caribe Hilton offers luxe beachfront stays with multiple dining options, lavish pools, and a private beach that feels like your own secret paradise—all while letting you sip on the legendary piña colada right where it was invented.
6 Postcards
The iconic Condado Vanderbilt blends historic Spanish Revival charm with luxe oceanfront suites, top-tier dining, a spa, and stellar service.
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Puerto Rican restaurant · San Juan
In a modest pink house on Loíza Street, José Enrique serves elevated Puerto Rican dishes with local flair and killer sweet potato mash.
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Castle · San Juan
Perched strategically in Old San Juan, Castillo San Cristóbal is the largest and most impressive Spanish fort in the Americas, blending rich history with breathtaking ocean views and intricate, well-preserved architecture that invites exploration.
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A chic adults-only boutique in Condado with luxe suites, a rooftop pool, DJ-lit Rolls Royce bar, and dazzling lagoon and ocean views.
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Nestled in the vibrant Distrito T-Mobile, this modern hotel boasts chic rooms, a lively bar, and an outdoor pool—all steps from nonstop entertainment action.
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Nestled in the vibrant heart of San Juan's Condado district, the Coral Princess is a cozy hotel with stylish rooms and a rooftop hot tub just steps from the beach.
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Nestled just a block from Condado Beach, the Radisson Ambassador Plaza blends cozy rooms with a rooftop pool and on-site dining for a relaxed stay.
Beer hall · San Juan
La Taberna Lúpulo in Old San Juan serves up 50+ local and global craft beers with killer Cuban sandwiches, wings, and bar snacks in a breezy historic vibe.
5 Postcards