Visiting Puerto Rico’s so-called “walled city” is like traveling back in time to another world. Old San Juan is the second oldest town in America and a stroll down its blue cobblestone streets provides a gateway to Puerto Rican history and culture. Visitors on historic tours and on foot marvel at the charm of the city’s pastel-colored colonial homes and architecture. Meanwhile, the surrounding military forts blend seamlessly into the slower-paced life of an authentic, modern-day Puerto Rican experience. History buffs, culture lovers, and sightseeing enthusiasts will all love our list of must-see landmarks and iconic places while visiting the remarkable city of Old San Juan.
Castillo San Felipe del Morro
The impressive citadel of “El Morro” was built in the 16th century by the Spaniards who settled in the Caribbean. It’s made up of six staggered levels combining barracks, dungeons and storerooms and provided a protective fortress for the city from attacks by sea. It even has some of its original cannons facing the ocean, as if poised and ready to repel attack. El Morro’s fortification proved strong, and earned the reputation of never being defeated by the enemy.
Castillo San Cristóbal
With the sea closely monitored for attackers, early settlers looked to protect their land. The fortress of Castillo San Cristóbal stretches across 27 acres and was built to guard the city from enemies approaching by land. The fortification is the largest one of its kind in the New World that was made by the Spaniards. The castle is also home to several military tales and island stories, called “Garita del Diablo”, or the Devil’s Sentry.
As the oldest residence in Old San Juan, Casa Blanca was turned into a museum for all to enjoy. It was first built as the home of Puerto Rico’s first governor, Juan Ponce de León. Tragically, Ponce de León died before he could ever live in the gorgeous home, but it was left for his descendants to reside in it.
Capilla del Cristo
The small sanctuary of “Chapel of Christ” is unique in that it was atypically built at the top of the walls of Old San Juan. It was an unusual decision made during colonial times, but legend may shed light on the puzzle. The story goes that two men raced their horses down the street, but one fell over the cliff and managed to survive. After being inspired by the survival, a sanctuary was built as a nod to the saints of health complete with an altar of embossed silver and two José Campeche paintings.
Santa María Magdalena de Pazzis Cemetery
Established in the 19th century, this peculiar and quirky cemetery was built by the Spaniards outside the city walls because of a pervasive fear of the afterlife. There’s also a superstitious reason for the cemetery’s oceanfront location. Early Spanish settlers believed that the deceased were just beginning a journey over to “the great beyond”. Being so close to the ocean was a symbol of the beginning of eternity. Santa María Magdalena de Pazzis Cemetery is also the final resting place of prominent Puerto Rican natives and residents.
Seminario Conciliar de San Ildefonso
Commissioned by the first Puerto Rican Bishop, Fray Juan Alejo de Arizmendi, the original building was completed in 1832. The Chapel’s artistic dome is stunning and worth a visit. Under the long teaching tradition of the Catholic Church, the seminar became a cornerstone in the development of public education in Puerto Rico.
La Fortaleza is the oldest state residence of the New World still in use as an executive palace. Its official name is “El Palacio de Santa Catalina de Alejandría”, or the Palace of St. Catherine of Alexandria. The palace conserves traditions including candlelit-only dining rooms and original Spanish objects from the colonial era.
Puerta de Agua or Puerta de San Juan
Look for the most colorful entrance to the “walled city” to find the “Door to San Juan”. It was also the main gate through which the priests and governors made their entrance to their investiture ceremonies.
Department of Treasury Annex
Situated inside the main square, “Plaza de Armas” served as the depository of the royal treasure of the island. The plaza was also the first headquarters of the provincial deputation that came before the modern legislative branches we have today.
San Juan Cathedral
As the second oldest church in America, San Juan Cathedral provides a rare look at medieval architecture during Spanish ruling in the New World. This is also the founding place of the world’s first archdiocese.
See one of the best-preserved churches on Puerto Rico at the Church of St. Francis. It was one of the first sanctuaries to be elevated in Puerto Rico and it still maintains the niches of people that were originally buried there.
Named after the father of Puerto Rican literature, Alejandro Tapia y Rivera, this architectural gem was built in 1832. It’s the oldest permanent theater in Puerto Rico and one of the oldest free-standing stages still in use under the U.S. flag.
PRIVATE HISTORICAL 2-HOUR WALKING TOUR OF OLD SAN JUAN
To see more of Old San Juan’s landmarks and historic attractions, take a tour to see what this 465-year old neighborhood has to offer. A private 2-hour tour of Old San Juan takes travelers through military forts, cafes, gardens, and galleries for an immersive experience. Soak up the culture and history while seeing the unique beauty of modern-day Old San Juan.