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A Weekend in Puerto Rico: A 3-Day Itinerary


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Day One: Old San Juan
A Weekend in Puerto Rico: A 3-Day Itinerary

The Night Tales in Old San Juan Tour

Photo © Zain Deane

Unless you're really trying to avoid it, you'll be flying into Luis Muñoz Marín International Airport, which is located in Carolina, about three miles away from San Juan. Assuming you get here in the morning, you'll be checked in and ready to start your vacation before noon. And your first stop will be Old San Juan.


  1. Maximize your time in the Old City by taking a walking tour. Click here for our suggested tour, or check with your hotel. You can also download a podcast of a walking tour here.

  2. When you're ready for lunch, you'll have a myriad options to choose from. The Parrot Club on Fortaleza Street is a fun place with excellent food, but if you want to eat like a local, head to La Fonda del Jibarito on Sol Street for cantina-style Puerto Rican specialties.

  3. Spend the rest of the day in the Old City, where there is never a dearth of things to do. Browse through one the city's many art galleries; shop for arts & crafts, jewelry, or fashionable clothes; visit one of the many museums; or simply walk around and enjoy the ambience of a city that was prospering before The Mayflower set sail.

  4. If you're not too tired by the evening, book yourself on a tour of "Night Tales of San Juan" with Legends of Puerto Rico. This is a fun, two-hour evening romp through the ciy's streets and buildings, full of historic anecdotes, folklore, and ghost stories. At night, the streets take on a different vibe, and Guide Debbie Molina brings them to life.

  5. You can eat very well in San Juan. Walk down Fortaleza Street to check out some of the hippest restaurants, like Dragonfly and Aguaviva. Many of these hotspots have a roaring bar and lounge scene after hours.

  6. If gambling is your thing and you're staying in the old city for the night, head to the Sheraton Old San Juan, the only casino hotel in Old San Juan.

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