Old San Juan, San Juan Antiguo, Viejo San Juan — no matter what you call this area, you can’t deny that it’s aging gracefully. This district in Puerto Rico’s capital dates back to 1521, and between its castles, colors, and cobblestones, it’s a sight for sore eyes.

So, if you’d like to add rich culture, fascinating history, or gorgeous architecture to your Puerto Rican itinerary, this neighborhood should be your first stop.

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One of the earliest European settlements in the New World, Old San Juan is a place where the cobblestones are tinted blue and the buildings are painted in pastels. As the easternmost island in the Greater Antilles, Puerto Rico was an important colonial possession for Spain, helping the European power ship goods to and from the Caribbean. Beginning with the 1539 construction of a major fortress, the Spanish built up Old San Juan to protect it from pirates and other invaders — but today, the city is both peaceful and undeniably charming.

In fact, Old San Juan’s military fortifications are now some of its most popular tourist attractions. Castillo San Felipe del Morro (a structure that’s usually just called ‘El Morro’) sits at the end of the peninsula, where its cannons and soldiers once protected it from falling into enemy hands. Today, visitors can explore the fortress to their heart’s content. Its ramparts are a beautiful place to enjoy a walk, and its watchtowers make for a perfect photo backdrop. Next to El Morro, a large grassy field doubles as the locals’ favorite picnicking and kite-flying site.

At 27 acres, Castillo San Cristobal is even larger than El Morro, designed to defend the old city from land-based attacks. It’s open for visits every day from 9 a.m. to 6 p.m., and like El Morro and several other structures in Old San Juan, it’s part of a UNESCO World Heritage Site.

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To further protect Old San Juan from unfriendly forces, Spanish urban planners also built up the city walls — but in modern times, the barriers are more useful for sightseeing than defending the city. For example, the Paseo de la Princesa is a pretty walkway that follows the walls, offering views of the bay and nearby buildings. While there, you’ll want to keep an eye out for Princesa Gastro Bar (a restaurant as well known for its ambiance as it is for its food), piragüeros (vendors selling piraguas, or snow cones), La Fortaleza (the governor’s mansion, a blue colonial building that’s visible from the paseo), and the Fuente Raices (a fountain celebrating Puerto Rico’s racial and ethnic roots). What’s more, since the Paseo de la Princesa faces west, it’s a perfect location to watch the sunset — so remember to come back later for end-of-the-day views.

Of course, there are plenty of sights to see within the walls too, since Old San Juan is home to many beautiful squares and incredible structures. Take the Plaza de Armas as an example. Although several government buildings line the square, puertorriqueños often use it as a meeting place or an endpoint on their evening walks, and it’s easy to see why. With its cafés offering outdoor seating and its large central fountain, the plaza is a great place to relax and people-watch.

Elsewhere in Old San Juan, you’ll find the Catedral de San Juan Bautista, which is one of the oldest cathedrals in the New World. It’s worth visiting for its elaborate ceiling and stained glass alone, although history buffs might also want to see the final resting place of Juan Ponce de León, who founded the city.

As you wander through Old San Juan, you might want to make it a game to discover your favorite buildings, streets, and landmarks. It takes about a full day to explore the entire quarter (and a lifetime to appreciate all of its details), so you’d better get started!

Have you been to Old San Juan? What did you like the most about this historic part of the city? Let us know in the comments.

Header image by Cristian Escobar
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Whitney Brown
Whitney Brown is a recent journalism graduate and travel writer based in Utah. She has lived in France and Ireland, and she's always planning her next big adventure. In addition to her passion for travel, Whitney loves archaeology, photography and floral design.