A visit to the so-called walled city is like traveling back in time. Walk up and down the blue cobblestone streets of the oldest city in America for a look into the core of Puerto Rican history and culture.
The charming, pastel-colored colonial architecture and military forts of Old San Juan blend in peace with modern, slower-paced life for an authentic Puerto Rican experience. Whether you’re a history lover, a culture buff, or a sightseeing enthusiast, here is a list of landmarks and iconic places that you should not miss while visiting this remarkable city.
Welcome to El Morro in Old San Juan.
Castillo San Felipe del Morro
Better known as El Morro, this impressive citadel is one of the largest fortifications built by the Spaniards in the Caribbean during the 16th century. Made up by six staggered levels that integrate barracks, dungeons, and storerooms, this fortress was designed to protect the city from attacks made by sea, and it still has some of the original cannons facing the ocean. In its history, El Morro was never defeated by the enemy.
Castillo San Cristóbal in Old San Juan.
Castillo San Cristóbal
Standing guard at the eastern gate, this fortress was built to guard the city from enemies approaching by land. Covering over 27 acres, this fortification is the largest one made by the Spaniards in the New World. This castle holds the famous Garita del Diablo, center to many military tales and stories in the Island.
View of Capilla del Cristo in Old San Juan.
Capilla del Cristo
Another landmark is the Capilla del Cristo. This small sanctuary was built at the top of the walls of the city, an unusual decision for colonial times. Legend has it that two men were racing their horses down the street and one of them fell over the cliff and survived. This inspired the construction of a sanctuary dedicated to the saints of health. Its altar is made of embossed silver and the room is decorated with two José Campeche paintings.
The historic Santa María Magdalena de Pazzis Cemetery in Old San Juan.
Santa María Magdalena de Pazzis Cemetery
This peculiar cemetery was established in the 19th century. The Spaniards built it outside the city walls because of their strong fear of the afterlife. Its oceanfront location derives from a superstitious belief that the deceased started a journey over to “the great beyond” and being close to the sea symbolized the beginning of eternity. This cemetery is the final resting place of Puerto Rico’s most prominent natives and residents.
Casa Blanca Museum in Old San Juan.
Casa Blanca
Turned into a museum, this is the oldest residence in Old San Juan. Casa Blanca was built to be the home of Puerto Rico’s first governor, Juan Ponce de León. Sadly, Ponce de León died before he could occupy it, but it was left for his descendants to reside in.
Cathedral Basilica of Saint John the Baptist, or La Catedral.
Catedral de San Juan
When compared to the rest of America, the structure of this church is a rare example of medieval architecture during Spanish ruling in the New World. The Catedral de San Juan is the second oldest church in the Americas, after the one built in the Dominican Republic. It was there that the world’s first archdiocese was founded.
The beautiful Governor's Mansion, aka La Fortaleza.
La Fortaleza
Officially named “El Palacio de Santa Catalina de Alejandría” (the Palace of St. Catherine of Alexandria), La Fortaleza is the oldest state residence of the New World still in use. This executive palace conserves traditions such as candlelit-only dining rooms and original Spanish objects from the colonial era.
Teatro Tapia is the oldest free-standing theater in Puerto Rico, and is still in use today.
Teatro Tapia
Also known as the municipal coliseum, this architectural gem was built in 1832 and named after Alejandro Tapia y Rivera, the father of Puerto Rican literature. Teatro Tapia is the oldest permanent theater in Puerto Rico and among the oldest free-standing stages still in use under the U.S. flag.
View of the Puerta de San Juan, the original entrance to the walled city when it was built in the 16th century.
Puerta de Agua or Puerta de San Juan
The Puerta de San Juan is the most colorful and known of all the entrances to the walled city. It was the main gate through which the priests and governors made their entrance to their investiture ceremonies.
Iglesia San Francisco was one of the first churches to be built on the Island.
Iglesia San Francisco
The Iglesia San Francisco was one of the first sanctuaries to be erected in Puerto Rico. It is the best-preserved church on the Island and it still maintains the niches of people that were buried there back in the day.
More San Juan Landmarks Not to Miss:
Seminario Conciliar de San Ildefonso
The original building was completed in 1832 and it was commissioned by the first Puerto Rican Bishop, Fray Juan Alejo de Arizmendi. The seminar became a cornerstone in the development of public education in Puerto Rico, under the long teaching tradition of the Catholic Church. The Dome at the Chapel is a work of art worthy of a visit.
Department of Treasury Annex
Located in the main square Plaza de Armas, it served as the depository of the royal treasure on the Island. It was also the first headquarters of the provincial deputation that preceded the modern-days legislative branches.
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