A Refreshing Nighttime Tour of Puerto Rico's Capital

Photo © Zain Deane

The Bottom Line

Among the best nocturnal excursions in Puerto Rico, "Night Tales in Old San Juan" is a journey into the history, mythology, and folklore of Old San Juan. This brisk two-mile tour is led by excellent local guides who know how to make the past come alive. If you love the character of the Old City, don't miss it.


  • An excellent way to see San Juan at night.
  • The tour takes you into buildings that are not accessible to tourists at night.
  • The energetic and knowledgeable tour guides make all the difference.


  • Not a good option if you're tired or don't like to walk.
  • Not a good option if you're not wearing comfortable walking shoes.


  • See if you can get guide Debbie Molinda to sing Noel Estrada’s lilting anthem, “En mi viejo San Juan,” for you.
  • Enjoy privileged access to buildings that are closed to the public after 5 pm.
  • Along the way, your guide will point out the locations of scenes from many Hollywood movies.
  • Learn about the ghost of the white lady in El Morro.
  • Hear the tragic story of the prisoner and the executioner's daughter.
  • Enjoy the warm tropical glow of the city at night.

These are just a few of the highlights of "Night Tales in Old San Juan." For two hours, you get to walk the city with your guide on a tour of Puerto Rico that isn't covered in the standard brochures. Founder Debbie Molina has done meticulous research to put together an entertaining trek into some of Old San Juan's historic buildings, along cobblestone streets, and around the walled city.

While you cover a lot of ground, the tour isn't overly strenuous, and there are several stops along the way where you can listen to your guide relate an old legend or pirate tale. Of course, it doesn't hurt that lamplit Old San Juan under the stars has a romantic and charming appeal at night.

Recently, Legends of Puerto Rico has added to its nocturnal adventures through Old San Juan with Spirits of Puerto Rico, a tour best appreciated by adults. The star attraction of this tour is​ the rum. Spirits of Puerto Rico combines dinner in Old San Juan with a sampling of eight different types of rum. Your taste buds are led by a local connoisseur who will educate you on the history of the drink while showing you how best to enjoy it. You even get a souvenir at the end of the tour.

Whether it's Night Tales or rum tales you're interested in, Legends of Puerto Rico provides two terrific nights out on the town. So grab your walking shoes, take your imagination with you, and bring your appetite.

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