How to Spend a Weekend in San Juan

San Juan is a gorgeous, historic city with so much culture, architecture, stunning beaches, and warm locals. The best part? It’s a quick flight from the US with no passport required. Read on for my tips on how to spend a weekend in San Juan.

  • Check into the Condado Vanderbilt Hotel. It’s sophisticated, elegant, and beachy all rolled into one. Bask in the luxury of your well-appointed guest room complete with 300 thread-count linens, plush bedding, and spa-inspired bath. Or opt for an ocean view suite with private terrace, sweeping views of the Caribbean sea, and personal butler service. The Condado Beach Club is pure heaven with multiple pools, oceanfront dining, and beach access. Don’t even get me started on the spa…you will just have to experience it for yourself.
  • Hit the Streets. Old San Juan’s historic Spanish architecture and old-world feel are not to be missed on a visit to Puerto Rico. Experience the brightly colored houses lining cobblestone streets, cool cocktail bars, and renowned Caribbean fusion restaurants with a guided foodie tour by The Spoon Experience. The Sunset Walk & Taste Tour was one of the highlights of my visit to San Juan.
  • Explore By Boat. Cruise San Juan Harbor to experience the most significant monuments of Puerto Rico, including the Spanish fort of El Morro, the Governor’s mansion of La Fortaleza, and the capitol building. Or take a short ferry ride from San Juan’s neighboring town of Ceiba to Vieques, best known as the island with the brightest bioluminescent bay in the world. Experience this incredible phenomenon with Abe’s Snorkeling & Biobay Tours or simply enjoy the island’s gorgeous beaches with sands ranging from pure white to sparkling soft black.
  • Grab a Table at a Rooftop Restaurant. San Juan’s spectacular coastline can best be viewed from above. My favorite spot in San Juan for amazing views and even better food and drinks is Kumo Rooftop. Located above the bohemian Aire De Olive boutique hotel, Kumo serves up inspiring Japanese fusion cuisine and delicious craft cocktails surrounded by the ocean breeze. What could be better?

For questions about travel to Puerto Rico or to book your next island vacation, contact me at or check out my other blog posts here.

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