Walking through Old San Juan: Seven things to do in Puerto Rico's Walled City
Cobblestones are blue in Puerto Rico's oldest city, evidence of its age and ties to the Old World. To walk on them is to step back more than five centuries when Juan Ponce de León walked ashore. Sailing ships from Spain came next, following the tradewinds across the Atlantic Ocean, their hulls filled with ballast stones stained blue by waste from iron smelting. They returned laden with treasure and, in time, coffee and sugar grown on island plantations.
By 1521, the settlement took its official name, San Juan Bautista de Puerto Rico. It became one of Spain's most important footholds in the New World for trade and a show of military might behind sturdy city walls.
Today, tourism drives Puerto Rico's economy. Old San Juan, roughly seven square blocks of Spanish colonial architecture and 16th- and 17th-century landmarks, ranks among its top attractions. A UNESCO World Heritage site, it sits on an island linked to modern San Juan by three bridges. Visiting is easy. Guided walking tours, some free, cover the highlights, and those who prefer to go on their own can download apps with maps and narration.
For U.S. citizens, visiting is especially convenient. Puerto Rico is a U.S. territory, so no passport is required, the dollar is the local currency and both Spanish and English are the official languages, though Spanish dominates.
Despite its rich past, walking through Old San Juan need not be a boring trudge through history. A lively city with a warm and welcoming populace, it offers hours of amusements, including these seven experiences:
Sip a piña colada
San Juan claims to be the birthplace of the piña colada cocktail, but just where that creamy mix of pineapple, coconut and rum was invented is in dispute. Some argue the bar in the Caribe Hilton on the mainland served the first drink in 1954, but bartender Jorge Ayala at Barrachina Bar and Restaurant in Old San Juan says no way. It was created right there in 1963. A marble plaque at the entrance on busy Fortaleza Street proclaims it.
No matter. The shady courtyard inside Barrachina makes a great place to relax during a walk in the old city. Get a brain freeze from the concoctions poured from whirring slushie machines at the end of the bar and chat up Ayala about goings on in Old San Juan. In answer to a compliment about his gregarious nature, he says "A monkey can serve a drink but a bartender is something else." And on the friendliness of the local people: "Yah, we send the (expletive) north."
Ayala happily jots down restaurant recommendations on a cocktail napkin - "Tell 'em Jorge sent you" - but you also can get a table inside the restaurant and dine on Barrachina's Puerto Rican and international dishes, including the Spanish specialty, paella.
Wave to the governor
San Juan's first settlers defended themselves from pirates and Carib Indians by building La Fortaleza - the fortress - between 1533 and 1540. A medieval tower remains following a massive 19th-century reconstruction transforming the building from a fort to a palatial residence for Puerto Rico's governor. The oldest executive mansion in the Western Hemisphere is a mix of baroque, Gothic, Arabian and neoclassical styles.
When the government is not in session, guided tours of the grounds, and maybe a peek inside, are offered on weekdays. Bring a photo ID and don't dress like you just wandered in from the beach.
Just outside the mansion, Fortaleza Street is lined with Spanish colonial buildings painted in a rainbow of pastels and adorned with eye-catching metal balconies. At certain times of the year, brightly colored umbrellas hang over the street to the delight of Instagrammers.
Fly a kite outside a fort
The most famous landmark in Old San Juan rises from a rocky promontory where the Atlantic Ocean meets San Juan Bay. Construction on Castillo de San Felipe del Morro, El Morro for short, began in 1539 and was completed in 1790 as a major military installation for Spain and later the United States.
It fought off attacks by water while its sister fort, Castillo San Cristobal on the other end of Old San Juan, staved off invaders by land. Both are administered by the U.S. National Park Service. Rangers give tours of El Morro's six-level labyrinth of barracks, vaults, sentry boxes, dungeons, dry moats, ramps and lookout points.
The broad lawn leading up to El Morro has long been a favorite spot to take advantage of stiff Atlantic breezes for flying kites, chiringas in Spanish. Join in the fun by buying one from a vendor nearby or at some drugstores in the old city.
Make a meal of chocolate
Ever tasted a chocolate grilled cheese sandwich? Or a rack of chocolate baby back ribs?
Chocolate Cortes, a fourth-generation family bean-to-bar chocolate manufacturing company opened Chocobar Cortes in 2013 with a menu incorporating chocolate in every dish. Chef Ricardo de Obaldia's culinary creations have made it one of the top restaurants in San Juan as well as an attraction for visitors to Old San Juan.
Yes, you can be conventional and order chocolate cake or a croissant or buy a box of bonbons, but why not make things interesting with a burger slathered in chocolate ketchup or a salad with chocolate vinaigrette?
Brunch is served all day every day with avocado toast and marbled waffles on the menu. If hot chocolate is too tame for you, try one of the cocktails, maybe the bloody choco-mary or an old fashioned served in a glass with a dark chocolate rim. Splurge on a pairing of three Caribbean rums with three dark chocolates. Happy hour, with a limited drink menu, happens Monday through Friday.
See an explorer's tomb
The oldest cathedral in the United States, and second oldest in the Americas, stands out as a fine example of medieval Spanish architecture. San Juan Cathedral, formally the Metropolitan Cathedral Basilica of Saint John the Baptist, sits on the site of Puerto Rico's first school dating from 1513. A wooden church built in 1521 fell in a hurricane and was replaced by the current building in 1540. It's been restored and remodeled several times over the centuries. Projects continue to this day.
Those centuries have not always been kind to the Gothic-inspired structure. In 1598, the English Earl of Cumberland looted it after capturing El Morro and it lost its roof in a hurricane in 1615. But its vaulted ceiling and stained-glass windows still inspire and glowing candles in quiet side chapels offer inner peace.
The cathedral is perhaps best known as the final resting place of explorer Juan Ponce de León. His body was disinterred from another church and placed here in a marble tomb in 1908. Just down a side aisle the wax mummy of St. Pius, a first-century Roman martyr, lies in a glass case.
Sleep in diplomatic digs
Just around the corner from the cathedral stands one of Old San Juan's newest boutique hotels, the adults-only Hotel Palacio Provincial. For most of its 200-year existence, the structure housed the center of diplomacy for Puerto Rico serving as the Provincial Council Building, the U.S. Post Office, and the U.S. Department of Agriculture and Commerce. Throughout the second half of the 20th century, it was Puerto Rico's Department of State, now next door.
Designed during the Historicist/Enlightenment Period, it was intended to be a large, public symbol, a visual icon of the Spanish crown with a grand exterior and richly appointed interior with a massive staircase and dual courtyards. In 1893, Infanta Eulalia of Spain, the youngest and last surviving child of Queen Isabella II, visited the building on her way to Chicago for the World's Columbian Exhibition celebrating the 400th anniversary of Christopher Columbus's landing in the New World. The hotel's presidential suite is named for this outspoken princess whose progressive views on politics, the independence of women and the equality of classes had tongues wagging in Europe.
In contrast to its colonial architecture, the hotel's 43 guest rooms and suites have a modern, minimalist decor with 12- and 14-foot-high beam ceilings, tall windows and juliet balconies. Three nights a week Sunset Rosé drinks are served around the rooftop pool and terrace overlooking the dome of the cathedral.
The hotel's open-air Consular restaurant serves breakfast and brunch, has a pizza oven and bar offering signature cocktails, and a dinner menu with mains that include octopus, steak, snapper and chicken.
Promenade like a princess
With the name Promenade of the Princess, you might picture an attractive walkway for royalty, but, in fact, this popular thoroughfare takes its name from La Princesa Prison, one of the most notorious jails in the Caribbean during colonial times. The building where prisoners sat in solitary for years and were executed by hanging has been restored and now houses the Puerto Rico Tourism Company, the territory's tourism office. You can see a few remaining jail cells inside.
Don't let the back story put you off this lovely tree-lined promenade extending a quarter mile along the old city walls, some as tall as 100 feet. Vendors selling food and crafts set up under lampposts along the promenade and street musicians serenade passersby, especially at night and on weekends. For a view of San Juan Bay, stand by the waterfront Raices Fountain with sculptures representing Puerto Rico's ethnic roots: European, African and native Taino.
You can start or end your walk at San Juan Gate, the only one of five passageways through the walls that remains. Standing 16 feet tall, it has been restored using techniques and materials from centuries ago. An inscription in Latin at the top translates as "Welcome those who come in the name of God." Passengers arriving by ship during the colonial era walked through the gate and proceeded uphill to the cathedral where they prayed in thanksgiving for their safe passage.
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If you go
Visitor information:
San Juan National Historic Site: nps.gov/saju/index.htm
Walking tours:
Free walking tour, osjfreetour.com/
Self-guided app, GPSmyCity
Where to stay:
Hotel Palacio Provincial, palacioprovincial.com/
Where to eat and drink:
Barrachina bar and restaurant, barrachina.com/
Chocobar Cortes, chocobarcortes.com/