Castillo San Felipe (El Morro)
The star of Old San Juan, El Morro juts aggressively over bold headlands, glowering across the Atlantic at would-be conquerors. The 140ft walls (some up to 15ft thick) date back to 1539, and El Morro is said to be the oldest Spanish fort in the New World.
Displays document the construction of the fort, which took almost 200 years, as well as El Morro’s role in rebuffing attacks on the island by the British, the Dutch and, later, the US military.
San Jose Church
The Iglesia de San José in the Plaza de San José is the second-oldest church in the Americas, after the cathedral in Santo Domingo in the Dominican Republic. Established in 1532 by Dominicans, this church, with its vaulted Gothic ceilings, still bears the coat of arms of Juan Ponce de León (whose family worshipped here), a striking carving of the Crucifixion and ornate processional floats.
For 350 years, the remains of Ponce de León rested in a crypt here before being moved to the city’s cathedral, down the hill. It remains the final resting place of José Campeche, one of Puerto Rico’s most revered artists, and the site of Puerto Rico’s oldest fresco painting.
Old San Juan Cathedral
Although noticeably smaller and more austere than other Spanish churches, the Catedral de San Juan nonetheless retains a simple earthy elegance. Founded originally in the 1520s, the first church on this site was destroyed in a hurricane in 1529. A replacement was constructed in 1540 and, over a period of centuries, it slowly evolved into the Gothic/neoclassical-inspired monument seen today.
Most people come to see the marble tomb of Ponce de León and the body of religious martyr St Pio displayed under glass. However, you can get quite a show here on Saturday afternoons when the limos roll up and bridal parties requisition the front steps. The main entrance to the cathedral faces a beautiful shaded park replete with antique benches and gnarly trees. On Sundays and holy days, you'll see worshippers in their finery.
Old San Juan Gate
Spanish ships once anchored in the cove just off these ramparts to unload colonists and supplies, all of which entered the city through a tall red portal known as Puerta de San Juan. This tunnel through the wall dates from the 1630s.
It marks the end of the Paseo de la Princesa, and stands as one of three remaining gates into the old city (the others lead into the cemetery and the enclave of La Perla). Once there were a total of five gates, and the massive wooden doors were closed each night to thwart intruders. Turn right after passing through the gate and you can follow the Paseo del Morro northwest, paralleling the old city walls for approximately three-quarters of a mile. Pause on one of the benches along the west side that have fine harbor and sunset views.
Museo of San Juan
Located in a Spanish colonial building, the Museo de San Juan is the definitive take on the city’s 500-year history. The well-laid-out exhibition showcases pictorial and photographic testimonies from the Caparra ruins to the modern-day shopping malls. There’s also a half-hour video about the history of San Juan and a small Saturday morning market in the pretty inner courtyard.
Guarded iron gates mark La Fortaleza, also known as El Palacio de Santa Catalina. This imposing building, dating from 1533, is the oldest executive mansion in continuous use in the western hemisphere. You can take a short guided tour that includes the mansion’s Moorish gardens, the dungeon and the chapel.
The original fortress for the young colony, La Fortaleza eventually yielded its military preeminence to the city’s newer and larger forts, and was remodeled and expanded to domicile island governors for more than three centuries.