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:
Join the celebrations!
Puerto Rico is celebrating the 500th anniversary of the founding of Old San Juan, the oldest city in the United States. Stay tuned for special events running through June 2022!
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
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.
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.
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.
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.
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.
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.
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.