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Old San Juan, Puerto Rico

Stroll through San Juan's first, and still most charming, neighborhood

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Rating: 5 out of 5 by EveryTrail members
Difficulty: Easy
Length: 2 miles
Duration: 1-3 hours

Overview :  Old San Juan is Puerto Rico’s quintessential colonial neighborhood. Narrow streets and plazas are still enclosed by thick fortress... more »

Tips:  This walk is best done in the morning to avoid the afternoon heat and cruise-ship crowds. The route is 2 mi (3 km); it will take half ... more »

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Points of Interest

1. Paseo de la Princesa

This street with a broad pedestrian walkway is spruced up with flowers, trees, benches, and street lamps and unfurls westward from Plaza del Immigrante along the base of the fortified city walls. It leads to the Fuente Raices, a striking fountain depicting the various ethnic groups of Puerto Rico. Take a seat and watch the boats zip across the... More

2. Puerta de San Juan

Dating back to 1520, this was one of the five original entrances to the city and is the only one still in its original state. The massive gate, painted a brilliant shade of red, gave access from the port. It resembles a tunnel because it passes through La Muralla, the 20-foot-thick city walls.

3. Plazuela de la Rogativa

According to legend, the British, while laying siege to the city in 1797, mistook the flaming torches of a rogativa—religious procession—for Spanish reinforcements and beat a hasty retreat. In this little plaza a monument of a bishop and three women commemorates the legend. The striking contemporary statue was created in 1971 by the artist Lindsay... More

Sitting atop the fortified city walls overlooking the harbor, the Fortaleza was built in 1533 as a fortress—and not a very good one. It was attacked numerous times and was occupied twice, by the British in 1598 and the Dutch in 1625. When El Morro and the city’s other fortifications were finished, the Fortaleza was transformed into the governor’s ... More

5. Capilla del Cristo

According to legend, in 1753 a young horseman named Baltazar Montañez got carried away during festivities in honor of San Juan Bautista (St. John the Baptist), raced down Calle Cristo, and plunged over its steep precipice. A witness to the tragedy promised to build a chapel if the young man’s life could be saved. Historical records maintain the... More

6. Catedral de San Juan Bautista

The Catholic shrine of Puerto Rico had humble beginnings in the early 1520s as a thatch-roof, wooden structure. After a hurricane destroyed the church, it was rebuilt in 1540, when it was given a graceful circular staircase and vaulted Gothic ceilings. Most of the work on the present cathedral, however, was done in the 19th century. The remains of... More

7. Museo Pablo Casals

The small, two-story museum contains memorabilia of the famed cellist, who made his home in Puerto Rico from 1956 until his death in 1973. Manuscripts, photographs, and his favorite cellos are on display, in addition to recordings and videotapes (shown on request) of Casals Festival concerts, which he instituted in 1957. The festival is held... More

With its vaulted ceilings, this little church is a splendid example of 16th-century Spanish Gothic architecture. It was built under the supervision of Dominican friars in 1532, making it one of the oldest churches in the Western Hemisphere. The body of Ponce de León, the Spanish explorer who came to the New World seeking the Fountain of Youth, was... More

9. Casa Blanca

The original structure on this site was a wooden house built in 1521 as a home for Ponce de León; he died in Cuba without ever having lived here. His descendants occupied the house’s sturdier replacement, a lovely colonial mansion with tile floors and beamed ceilings, for the next 250 years. It was the home of the U.S. Army commander in Puerto... More

10. Castillo San Felipe del Morro

At the northwestern tip of the Old City is El Morro (“the promontory”), a fortress built by the Spaniards between 1540 and 1783. Rising 140 feet above the sea, the massive six-level fortress was built to protect the harbor entrance. It is a labyrinth of cannon batteries, ramps, barracks, turrets, towers, and tunnels. Built to protect the port, El ... More

11. Museo de San Juan

A bustling marketplace in 1855, this handsome building now houses the small San Juan Museum (formerly the San Juan Museum of Art and History). You’ll find exhibits of Puerto Rican art, plus tableaux and audiovisual shows that present the island’s history. Concerts and other cultural events take place in the huge interior courtyard.

Address: 150... More

12. Castillo San Cristóbal

This huge stone fortress, built between 1634 and 1785, guarded the city from land attacks from the east. Even larger than El Morro, San Cristóbal was known in the 17th and 18th centuries as the Gibraltar of the West Indies. Five freestanding structures divided by dry moats are connected by tunnels. You’re free to explore the gun turrets (with... More

13. Plaza de Colón

A statue of Christopher Columbus stands atop a soaring column and fountain in this bustling Old San Juan square catercorner to Castillo San Cristóbal. Originally called St. James Square, it was renamed in honor of Columbus on the 400th anniversary of his arrival in Puerto Rico. Bronze plaques on the statue’s base relate various episodes in the... More