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Historic Puerto Rico: Exploring Old San Juan

Written by Chris Osburn

This blog post was updated on May 12, 2020.

Bienvenido a Viejo San Juan — Welcome to Old San Juan!

The second oldest Europe-established capital in the Americas, this celebrated city is still very much a vibrant destination for whatever floats your vacation boat. For some of the Caribbean’s best preserved historical sites, cool cocktails, hot dancing, and a variety of fun-in-the-sun activities, Old San Juan is a sensational place to be.

Have a look at our guide to the best of Old San Juan, and start planning your getaway to the Puerto Rican capital’s most historic quarter pronto!

Sip the Original Piña Colada at Barrachina

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Do you like piña coladas? Then be sure to limber up your elbows and head over to the Barrachina restaurant– rumored to be the birthplace of Puerto Rico’s national drink. While you’re here, we also suggest bringing a huge appetite; this spot is famous for its mouthwatering paella!

Ready to take a bite out of this scintillating city? Get going with cheap flights to San Juan here!

Stroll the Calle Fortaleza

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Before, after, and in-between your piña coladas at Barrachina, take a stroll along Calle Fortaleza, one of Puerto Rico’s most celebrated streets for restaurants and nightlife. The best restaurants, drawing in locals and visitors alike, are mostly around SoFo (South Fortaleza). Here, seafood lovers will find the daily offerings too delicious to pass up! During the day, Fortaleza is a retail paradise with lots of boutique shops and opportunities to purchase authentic gifts and souvenirs.

Stand Atop El Castillo de San Felipe del Morro

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This 16th century citadel guards San Juan Bay and provides visitors with commanding views and insight into Puerto Rico’s unique past. It’s a UNESCO World Heritage Site, (as are so many Old San Juan sites, and indeed the entire neighborhood itself) and a San Juan National Historic Site.

Visit the Cathedral of San Juan Bautista

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One of Puerto Rico’s oldest and most beautiful buildings, and the second oldest Roman Catholic cathedral in the Americas, the Cathedral of Saint John the Baptist dates back to the 1500s. As glorious as it is to behold from the outside, be sure to go in to view its awe-inspiring stained glass windows, the tomb of Spanish explorer Ponce de Leon, and the mummified remains of San Pio. Entry is free but donations are appreciated.

Relax in the Paseo de la Princesa

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Lined with trees and antique lampposts, this picture perfect promenade exudes Old World charm and serves as an ideal setting for a relaxing and scenic walk. Enjoy the views of San Juan Bay, and admire the Paseo’s centerpiece Raíces Fountain, with its sculptures depicting the island’s Taino, African, and Spanish heritage, while taking it easy and sightseeing at a leisurely pace.

Have you ever been enchanted by San Juan Viejo? Let us know your favorite hangouts in the Old City in the comments section below.

About the author

Chris Osburn

Chris Osburn is a freelance writer, photographer, consultant, and curator and the driving force behind the long running and award winning blog, Originally from the American Deep South, Chris has lived and worked all over the world and has called London home since 2001.

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