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How to Explore 500 Years of History and Culture in Old San Juan

Armed with artist Mauro Díaz’s insider knowledge, celebrate the 500th anniversary of the Puerto Rican capital and explore centuries-old traditions, art, and architecture.

How to Explore 500 Years of History and Culture in Old San Juan

El Morro

Founded in 1521, San Juan holds the title of oldest city in the United States, boasting more than five centuries of history spanning native Taíno, Spanish, African, and American heritages. Today, this 500-year-old city delights visitors with its rich history, vibrant creative scene, multi-cultural legacy, and mouthwatering culinary offerings.

Local artist and surfer Mauro Díaz spends his days exploring Puerto Rico by both land and sea. Born and raised in Puerto Rico, Díaz finds inspiration everywhere he looks—from the juxtaposition of historical architecture against a backdrop of crystalline sea, to the bursting present-day creativity spread across the capital city of San Juan.


Puerto Rico defines Díaz’s two passions, artwork and surfing.

Photo by Claire Murphy/@clairemrphy

500 years of inspiration

“Puerto Rico is much more than a hotel in front of the beach,” says Díaz. He recommends visitors start with a walk around Viejo San Juan, including a stop by the city’s historic fort, El Morro. Constructed in 1539 to defend the city from attacks by sea, the Spanish-built citadel stands sentinel above fortified city walls, verdant fields, and the distinctive blue cobblestones of Old San Juan.

Travelers can then venture next door, to the former 19th-century military barracks of the Cuartel de Ballajá. The barracks now house the Museo de las Américas, whose exhibits shine a light on Puerto Rico’s layered cultural heritage. For a moment of quiet, Díaz suggests people enjoy the interior courtyard, which will “make you feel miniscule… like you are in a Roman arena, surrounded by sky.”


Cuartel de Ballajá

Across the street, Museo Casa Blanca offers the oldest example of Spanish architecture in all of the U.S. territories. Initially built to house Puerto Rico’s first governor, Juan Ponce de León, today it is known for its well-preserved 16th- and 17th-century décor.

A five-minute walk south stands the Catedral de San Juan Bautista, the second-oldest church in the Americas. Immediately west, amblers encounter the cherry-red Puerta de San Juan, once the main entrance to the walled city of San Juan and today a picturesque waypoint on the seaside Paseo de la Princesa. A couple minutes south from there, La Fortaleza remains the New World’s oldest executive mansion in continuous use, serving as the governor’s residence since 1533.

Art through the ages


The city walls of San Juan.

Beyond Old Town, Díaz recommends a visit to the Museo de Arte de Puerto Rico for a taste of the Island’s artistic mastery. Boasting 24 galleries and an expansive sculpture garden, the museum displays art from the 1600s to the present day, including works from local masters such as Julio Tomás Martínez, whose painting La ocupación de Utuado en 1898 inspired Díaz to explore competing colonial powers’ impacts on Puerto Rico.

Showcasing the Island’s current creativity, Pública Espacio Cultural holds exhibits featuring live performances and visual art, as well as monthly markets. El Bastión offers art shows and dance classes in Old San Juan. Galleries such as Amor Fuego, Embajada, and La Casa de los Contrafuertes offer rotating art installations.

Discovering Puerto Rico’s roots


Parque Ceremonial Indígena de Caguana

Michelle Camacho

Before the Spanish arrived in Puerto Rico in 1493, tens of thousands of native Taínos inhabited the Island, excelling at agriculture, fishing, and navigating. Now, just an hour and a half drive from San Juan, one of the most important Taíno cultural sites in the Caribbean has been unearthed in the mountain town of Utuado. Parque Ceremonial Indígena de Caguana features ceremonial plazas, petroglyphs, pottery shards, and 14th- and 15th-century limestone artifacts. “It is a mesmerizing experience to be in spaces that were sacred to the indigenous tribes,” reports Díaz.

Due south, in the city of Ponce, Hacienda Buena Vista provides an immersive view of Puerto Rico’s 19th-century coffee production. A restored historical site, this hacienda includes a Spanish colonial house, slave quarters, and coffee processing facilities, and offers tours to educate visitors about the roles that both plantation owners and enslaved people played in Puerto Rico’s coffee-producing history.

Delighting in Puerto Rico’s present


The Loíza neighborhood


To celebrate Puerto Rico’s multicultural flavor, Díaz suggests visitors get a taste of the local cuisine. La Casita Blanca offers Puerto Rican dishes like cod arepas, grilled garlic shrimp, and tres leches cake. Berlingeri Cocina Artesanal prides itself on modern vegetarian specialties enhanced with local ingredients. Barrachina not only offers classic island fare, but also lays claim as the inventor of the piña colada.

In the end, the best way to celebrate San Juan’s 500-year anniversary is to “ask locals about the history of the town and hear their stories,” according to Díaz. “Have a good time, and always remember to respect the locals, the land, and the Island itself.”

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