A visit to the so-called walled city is like traveling back in time. As the second oldest town in America, a walk up and down blue cobblestone streets of Old San Juan is a gateway into the core of Puerto Rican history and culture.

The charming pastel-colored colonial architecture and military forts blend in peace with modern, slower-paced life for an authentic Puerto Rican experience. Whether you’re a history savvy, a cultural buff, or a sightseeing enthusiast, here is a list of landmarks and iconic places that you should not miss while visiting this remarkable city: 

Front view of El Morro in Old San Juan.

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. 

Outside view of the Castillo San Cristóbal in Old San Juan.

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 tails and stories in the Island. 

View of Capilla del Cristo in Old San Juan.

View of Capilla del Cristo in Old San Juan.

Capilla del Cristo

Another landmark is the Capilla del Cristo. This small sanctuary was atypically built at the top of the walls of the city, an unusual decision made in 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. 

View of the historic Santa María Magdalena de Pazzis Cemetery in Old San Juan.

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. 

Inside view of the Casa Blanca Museum in Old San Juan.

Casa Blanca Museum in Old San Juan.

Casa Blanca

Turned into a museum, this is the oldest residence in Old San Juan. It was built to become 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 it. 

Inside view of the San Juan Cathedral.

Cathedral Basilica of Saint John the Baptist, or La Catedral.

Catedral de San Juan

When comparing 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 America, after the one built in the Dominican Republic. It was there that the world’s first archdiocese was founded. 

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. 

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. 

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. 

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. 

Iglesia San Francisco

The Iglesia San Francisco was one of the first sanctuaries to be elevated 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. 

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. It is the oldest permanent theater in Puerto Rico and among the oldest free-standing stages still in use under the U.S. flag.

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