A Weekend in San Juan

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Advisor - Caitlyn Cronin
Curated By

Caitlyn Cronin

  • San Juan

  • Arts & Culture

  • Food & Wine

  • History

  • Local Culture

  • Coastal

  • Sightseeing

Old San Juan is a vibrant and colorful historic district in the capital of Puerto Rico.
Curator’s statement

San Juan, the vibrant capital of Puerto Rico, is a captivating blend of rich history, colorful culture and breathtaking coastal beauty. I frequent San Juan as my best friend lives in the city and with its warm tropical climate, lively arts scene and a mix of Spanish, African and Taíno influences, I can confidently say that San Juan is a must-see destination.

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Where to stay in San Juan

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Things to do in San Juan

El Morro is a historic fortress and iconic landmark in San Juan.

Old San Juan: The city's historic heart, Old San Juan, is a UNESCO World Heritage site with narrow cobblestone streets, colonial architecture and iconic pastel-colored buildings

El Morro and San Cristobal: Explore these historic forts that offer beautiful panoramic views of the Atlantic Ocean.

La Placita: Indulge in the lively atmosphere of La Placita, where locals and visitors alike gather for music, dance and authentic Puerto Rican cuisine.

Relax at the Beaches: Enjoy the sun and sand at the beautiful beaches in and around San Juan, such as El Escambron and Ocean Park Beach.

Rum Tasting: Puerto Rico is home to Bacardi and Ron del Barrilito, among other rum distilleries. I have not done the Bacardi tour and tasting, but I absolutely LOVED the Ron del Barrilito tour and tasting! It is a small group with a guide who takes you around the property as you learn about the history of the rum from the little barrel. It is followed by a tasting of their five different rums (the three-Star is my favorite).

Day trips

El Yunque: El Yunque, the only tropical rainforest in the U.S. National Forest System, enchants visitors with its lush greenery, diverse wildlife, and cascading waterfalls, providing a captivating natural retreat in Puerto Rico.

Boat to Palomino or Icacos: rent a boat out of Fajardo to one of the smaller islands off the eastern coast of the island!

Chinchorreo through Guavate: if you’re looking to cool down a bit, I definitely recommend a “chinchorreo” into the mountains toward the center of the island! A chinchorreo is basically a group of people bar hopping in a bus/van. Guavate is a great place to do this to truly experience the culture of Puerto Rico: dancing, singing, authentic food, local markets, etc.

Places to eat & drink in San Juan

Pira-Rum has brought the tradition of Old San Juan to cocktails.

Lunch and Dinner

Santaella: Specializing in local cuisine using local ingredients, Santaella showcases the energy of the island’s ‘cocina criolla.’

Cocina al Fondo: This locally inspired restaurant in San Juan run by James Beard Award-winning Chef Natalia Vallejo is absolutely worth visiting.

Casita Miramar: Coined as traditional up-scale Puerto Rican food, Casita Miramar is sure to be a crown favorite.

Vianda: Vianda is a farm to table restaurant that prides itself on focusing on what Puerto Rico best offers: its agriculture and its hospitality.

Casa Pimentón: If you’re looking for Italian and pizza on the island, this is the place to visit!

Drinks

La Factoría: A renowned bar and cocktail lounge in Old San Juan, celebrated for its innovative mixology, lively ambiance and vibrant contribution to the city’s nightlife.

Bar Catedral Rooftop: Covering the top floor of the Decanter Hotel, Bar Catedral Rooftop comes with spectacular views of Old San Juan.

Pira Rum: A very Instagrammable bar located in Old San Juan.

Advisor - Caitlyn Cronin

Travel Advisor

Caitlyn Cronin

Get in touch with Caitlyn

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For more travel tips, check out Fora Advisor Shantele Allen’s guide, Caribbean Vacation in San Juan, Puerto Rico.

This guide is part of our ongoing series on travel to San Juan.