Begin your walking tour at the visitor center of the Puerto Rico Tourism Company. The building is on the waterfront at Plaza de la Dársena, just across the street from Pier 1. Here you can pick up maps, brochures and a free daiquiri sample before venturing into the heart of Old San Juan.
From the visitor center, follow the paved brick walkway west along the port toward Paseo de La Princesa. The U.S. Customs House with its pink stucco exterior and Moorish details will be on your left; the towering Art Deco edifice of Banco Popular will be on your right across the street. Two orange columns mark the entrance to the Paseo, the tree-lined promenade winding along the ancient city wall and the rocky shore of San Juan Bay. Pocket parks and benches provide resting places along the way. The massive wall, known as “La Muralla,” stands 42 feet high and was constructed with parallel sections of sandstone blocks. Sand poured between the sections helped absorb the impact of cannon balls. Completed in 1782, the towering fortification stretches for 3.4 miles and once enclosed the entire colonial capital. Garitas, or sentry boxes, crown the wall at prominent points along the bay.
Toward the end of the main promenade is La Princesa, the old penitentiary. Now restored, the gray-and-white building houses a visitor center for the Puerto Rico Tourism Company and a gallery for local artists. At the point where the Paseo meets San Juan Bay, the Raíces fountain by sculptor Luís Sanguino honors the three cultures—Taíno, Spanish and African—comprising modern Puerto Rico.
Following the walkway into the deep shade of banyan trees, you'll pass the jagged metal spikes of Crecimiento, a sculpture by Carmen Inés Blondet. Above the wall are the gardens of The Fortress (La Fortaleza), the governor's mansion.
Rounding a bend in the stone wall, you'll approach the Puerta de San Juan, or San Juan Gate, as seafaring guests approached the city for centuries. The red gate was one of six in the original fortification, and its massive wooden doors were locked at sundown to guard against attack. Disembarking from their ships, visiting dignitaries were greeted here and escorted to the cathedral for an official blessing. The Latin inscription reads, “Blessed is he who comes in the name of the Lord.”
From here, the Paseo continues along the wall to the foot of Castillo San Felipe del Morro (El Morro). Future plans call for the trail to access the fort, but for now, it ends below the water battery. Should you decide to walk out to the point and back, you'll see many of Old San Juan's furry residents lazing in the sun; a colony of feral cats is protected by the national park service and fed by a local organization called “Save a Gato.”
To continue the walking tour, pass through the gate and take a sharp left to follow the steep walkway up the hill on Calle Recinto del Oeste toward the Plazuela de la Rogativa. This little plaza at the top of the wall is home to La Rogativa, a striking sculpture created by Lindsay Daen to mark San Juan's 450th anniversary. The bronze statue of a bishop and three women bearing torches pays tribute to a beloved local legend: during a British siege in 1797, it is said that the enemy saw the lights of a religious procession and fled, thinking Spanish reinforcements were on the way.
The street splits just above the plaza; follow the lower road through the white gate and into the shade. On your right will be the walled gardens of Casa Blanca, or the White House Museum. On the left, you will pass Casa Rosada, the Pink House, a former Spanish barracks and now a day-care center. Follow the long walls of the Institute of Puerto Rican Culture and the Academy of Fine Arts to the top of the hill, where you will face the low citadel of Castillo San Felipe del Morro (El Morro). It's a quarter-mile across the field; the grounds are closed to motor traffic. On weekends, you’ll often see families flying kites and picnicking on the grass. The fortification is part of San Juan National Historic Site. Water fountains and restrooms are available at both sites.
Built on a promontory high above the harbor, El Morro repelled attacks by the British, Dutch and French over the course of three centuries. Construction began in 1539 and continued until 1787. Surrounded by a dry moat, it covers six levels—from the water battery to the upper bastions—and includes kitchens, barracks, a chapel, gun batteries, dungeons, secret tunnels and a lighthouse. Looking west from the battlements you can see El Cañuelo, smallest of the three forts built to defend the harbor. The first wooden fort, San Juan de la Cruz, was built on La Isla de Cabras (Goat Island) about 1610. Destroyed by the Dutch, it was reconstructed in stone in the 1670s.
To the east, you have a bird's-eye view of the beautiful Cementerío de San Juan with its pink-domed chapel dedicated to Santa Maria Magdalena de Pazzis. The colorful neighborhood beyond the cemetery, La Perla, is picturesque from a distance but should not be explored on foot—it's one of few places in Old San Juan deemed unsafe for tourists.
Leaving the fort, follow the main walkway across the field and through the traffic intersection on Calle Norzagaray into the Plaza de Ballajá. This was once the city's hospital center. The first building on the right, the 1858 Antiguo Manicomio, housed the mentally ill. It now contains classrooms for the Puerto Rican Academy of Fine Arts.
Across the plaza, the three-story Cuartel de Ballajá was a barracks for 19th-century Spanish soldiers and their families. With its massive inner courtyard, the building covers nearly 3 acres. Take time to walk upstairs to the second floor, where the Museo de las Américas displays archeological artifacts and colorful examples of folk art.
Leaving Cuartel de Ballajá, walk to the top of the plaza; on the right is the White House Museum (Casa Blanca). This fortified mansion was built in 1523 for Juan Ponce de León by his son-in-law. The conquistador died before its completion, but his family lived here for 250 years until the Spanish government acquired it for a military headquarters. Three centuries’ worth of antiques decorate the museum home, and the gardens are a shady spot to rest.
Leaving Casa Blanca, cross the plaza to face the statue honoring Eugenio Maria de Hostos, a 19th-century educator who advocated an independent confederation between Puerto Rico, the Dominican Republic and Cuba. Follow the street leading east between the Cuartel de Ballajá and its yellow counterpart, the Antiguo Hospital de la Concepción, toward the white Church of San José.
On the left, you will enter the top terrace of the Plaza del Quinto Centenario, commemorating the 500th anniversary of Columbus’ arrival in the New World. The giant stone pillar, Tótem Telúrico, was created by sculptor Jaime Suárez as a symbol of Caribbean Indian cultures.
Beneath the monument is a parking garage, and the busy street of Calle Cristo emerges from under the terrace into Old San Juan. Watch for fast-moving taxis and trucks as you return to the walking route. The street will jog toward the right, bringing you into Plaza San José.
The statue of Ponce de León at the center of this square was created by melting down British cannons. It's a popular gathering place for local residents. The plaza's heart is La Iglesia de San José, the second-oldest church in the Western Hemisphere. Dominican friars began building the original chapel in 1532. The interior features vaulted Gothic ceilings, a collection of religious paintings and frescoes, Ponce de León’s family coat of arms and a figure of Christ on the cross that may date to the mid-16th century.
Follow the steep, cobbled street of Calle Cristo as it leads downhill from Plaza San José toward the port. On the right, you’ll pass the 1842 Seminario Concilar and the 17th-century El Convento Hotel, a former Carmelite convent. The hotel faces the shaded Plaza de la Catedral and the graceful Catedral de San Juan Bautista. This rare example of Caribbean medieval architecture features a circular staircase, vaulted ceilings and venerated relics. The marble tomb of Juan Ponce de León stands near the transept.
Continue south on Calle Cristo past the designer shops and T-shirt stores to Calle Fortaleza. One block to your right is the oldest executive mansion still in use in the Western Hemisphere, The Fortress (La Fortaleza). Also known as El Palacio de Santa Catalina, the blue-and-white building has been the residence of Puerto Rico's governors and the seat of government for more than 4 centuries. Guided tours of the gardens are offered in English; proper attire is required.
Calle Cristo ends at the gated Christ Chapel (Capilla del Cristo), a small stone chapel built in honor of a fabled miracle. Legend says that a horse and rider plunged off this cliff during a festival race in 1753, but prayers saved the rider’s life. (Some versions of the story say he died but his mount survived.) Nevertheless, this tiny chapel was erected in thanksgiving. The building is only open to the public on Tuesdays, when the glass doors are unlocked to reveal a golden altar and painted icons. The Parque de las Palomas atop the city wall offers a good view of the port. Keep your camera handy—when a visitor buys a bag of dried corn to feed the pigeons, it can look like a scene from Hitchcock's “The Birds.”
Also within the cul-de-sac at the end of Calle Cristo are the Book Museum and Library (La Casa del Libro), a restored and furnished 18th-century residence holding a specialized library of 4,000 antique books; and the Centro Nacional de Artes Populares y Artesanías, a popular place to shop for handcrafted souvenirs.
To end the tour early and take a shortcut back to the waterfront, walk behind the chapel and follow Calle Tetuán east, passing Casa Ramón Power y Giralt—the former home of a Spanish military hero and now headquarters of the Conservation Trust of Puerto Rico (Para la Naturaleza)—and the pink Iglesia de Santa Ana. Turn right on Calle San Justo to finish your tour at the cruise ship piers.
To continue the full walking tour, return north on Calle Cristo to Calle Fortaleza and turn right. Take a left at the next corner onto Calle de San José to reach Old San Juan’s main square, Plaza de Armas. The statues on the fountain represent the four seasons. The former Spanish treasury on the left, La Intendencia, is headquarters of the Puerto Rico Department of State. City Hall (Casa Alcaldía) fronts the plaza on Calle San Francisco. The building's façade was said to have been inspired by the city hall in Madrid.
There are two drug stores on the northeast corner if you need to pick up any supplies. Continue past them on Calle San Francisco. A little farther on is the Plaza de Salvador Brau with its seated statue of the 19th-century Puerto Rican writer. Adjoining the plaza is the 1756 Franciscan Chapel.
The street will open onto Columbus Square (Plaza de Colón), where a statue of the explorer stands on the stone column above a fountain. A two-sided sign with maps of the island and Old San Juan will help you get your bearings. At the bottom of the plaza is El Tapia Theater (Teatro Tapia), one of Puerto Rico's most cherished cultural monuments. Built in 1832, the restored theater is one of the oldest still in use in the Western Hemisphere. To the east, the gray-and-white Antiguo Casino is an opulent example of French Second Empire architecture, now used for state functions.
The walls of Castillo San Cristóbal dominate the northeast corner. From Plaza de Colón, follow the street up the hill to the gate of the city’s main defense against land attacks. The 27-acre (11-hectare) fortification was the largest ever built by the Spanish in the New World. Visitors can climb the ramparts and wander a maze of tunnels inside this UNESCO World Heritage Site, which remains a monument to military engineering. Take time to explore the museum exhibits of armor and weaponry.
From Castillo San Cristóbal it’s a short walk back down to the waterfront. If you’re ready for a break, hop aboard the free trolley (although it may be crowded if cruise ships are in port).
On foot, walk back through Columbus Square (Plaza de Colón) and follow Recinto Sur; El Tapia Theater (Teatro Tapia) will be on your left. At the intersection of Recinto Sur and Calle Tetuán, you'll pass a triangular plaza and a statue of Arturo Somohano, composer and director of the San Juan Symphony Orchestra. International restaurants along Recinto Sur offer everything from sushi to Italian to Transylvanian cuisine. Passing the six-story Galeria, you'll see the U.S. Post Office and Courthouse with its Moorish roof. Turn left on Calle Tanca to come full circle on your walking tour of Old San Juan.