Weekend Escape in Old San Juan

Home to artists, musicians and international romantics, Old San Juan has breathtaking vistas, hip cafés and bars, some of the finest restaurants in the Caribbean and world-class galleries and museums.

By Xavira Neggers Crescioni
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N ot much bigger than a square mile, Old San Juan is nonetheless filled with infinite wonder, offering visitors something new regardless of how many times they have walked its narrow, cobblestone streets.

Founded in 1521, it is the best place in the Western Hemisphere to see restored Spanish colonial architecture, including domed cathedrals of ethereal beauty and massive stone fortresses looming over the city’s rocky Atlantic coast. The Old City features restored buildings from other eras, with Art Deco to Neo-colonial styles, and with its thriving cultural and entertainment venues, the city is woven into the fabric of contemporary Puerto Rican life. Sanjuaneros don’t call it Viejo San Juan, but rather San Juan.


Make sure to schedule sufficient time just to walk around and get lost in the Old City, which has rustic blue cobblestone streets and postcard views around every turn. You’ll get lost in time meandering along its quiet side streets, which climb the hill from San Juan Bay to a headland overlooking the Atlantic and are lined with pastel residences with Bougainville-draped balconies. Wander over to the lively row of restaurants and bars lining San Sebastian Street and in the SoFo (South Fortaleza) section around Fortaleza and Recinto Sur Streets and you’ll think you’ve stepped into the most fashionable party in the Caribbean, a multi-cultural fest that is cutting edge contemporary.

Before lunch, poke your head inside the gorgeous San Juan Cathedral, a wonderful respite from the heat that will inspire you with beautiful sculptures and paintings every bit as impressive as the magnificent building in which they are found. The cathedral, the second oldest in the Western Hemisphere, is the final resting place for Juan Ponce de Leon’s remains. Across the street, a former historic convent has been reborn into a luxury hotel (El Convento).

Have yourself some roam around time and begin soaking up this great city. Check out the main plazas – Plaza Colon, Plaza de Armas, and Plaza San Jose – they are a beehive of activity as San Juan prepares for the weekend. You should also take a stroll along Paseo de la Princesa, the gorgeous bayside promenade, which features the gorgeous fountain and sculpture called “Raices,” a sensual ode to the heritage of Puerto Ricans, and the San Juan Gate, the ancient entrance to the Old City. Grab an inexpensive, gourmet Puerto Rican coffee at Cuatro Estaciones cafe in Plaza de Armas, or try a piragua, a tropical fruit flavored ice, which is sold from a sidewalk cart right beside the gate.

Old San Juan is home to Puerto Rico’s capitol (El Capitolio), governor’s mansion (La Fortaleza), Supreme Court and city hall, all are beautiful examples of Spanish colonial or Neo-colonial architecture. The tour will take you along the 20-foot thick walls that still surround some parts of the city; to the hidden beauty of luxurious interior patios; to public art that graces nearly every nook and cranny of the best preserved colonial city in the Americas.

Other Old City sites include La Princesa, a former penitentiary that currently houses the Puerto Rico Tourism Company headquarters, the 18th century Capilla del Cristo chapel, and new mega cruise ship ports.

Viernes Social (Friday evening), is the most popular night to go out and party in Puerto Rico, regardless of what it is you are looking to do and where it is you want to do it. San Sebastian Street, from Cristo Street to San Justo Street, is home to many bars and restaurants, and has been for centuries one of the best spots in San Juan to party. The street really comes alive during the annual San Sebastian Street Festival in mid-January, a four-day arts, cultural, culinary and music fest that is one of the best parties in the entire Caribbean, but there’s plenty of action weekend nights and the rest of the year as well.

Make sure to stroll around the corner on Cristo Street to have a night cap at El Batey (101 Cristo Street), which offers Piña Coladas or Mojitos, but has been a must-stop for worldly travelers for years. The legendary bar has bare, eroded stone walls covered in graffiti and customer’s names, and random business cards strung together form shades for the lights. The talk at the bar is as real and as unvarnished as the décor, and the juke box, is what it is all about: from old Bob Dylan to the Rolling Stones, James Brown to Aretha Franklin.

Instant recall of Old San Juan’s original purpose to house and protect the rich port of the San Juan Bay is triggered with a visit to Fort San Felipe del Morro and Fort San Cristobal, a United Nations World Heritage Site.

San Cristobal guards the land entrance and sea approach to the bay. Make sure to explore the underground tunnels and dungeons; one has a drawing of a boat and seascape by a captured sailor sentenced to death. Check at the Devil’s Sentry Box, the most remote of the watchtowers from the fortress offering breathtaking views.

This tour is the perfect aperitif for a visit to San Felipe del Morro, the massive fort that guards the narrow entrance to the San Juan Bay and protected it from pirate attacks. It overlooks 100-foot of granite cliffs and providing marvelous vistas of the Atlantic Ocean, the iconic city cemetery and the coastal village La Perla.

Make sure to budget time to fly a kite or just chill out on the grassy grounds of the El Morro after your visit, which sprawl across the oceanfront bluff overlooking the city’s historic cemetery, home to Puerto Ricans must illustrious citizens, the coastal village La Perla beyond that. You can buy one in front of the fortress grounds from the street cart vendors, which also sell cold refreshments.

You can get delicious island food in a rustic Puerto Rican countryside setting without ever having to leave the Old City. Raices has it all. The restaurant is beautifully outfitted with local arts and crafts and the waitresses and waiters are decked out in folkloric dress. The best way to sample local specialties is with the “typical festival” platter, which has meat turnovers, stuffed fried plantain fritters, codfish fritters, and mashed cassava, and delicious plantain soup. The stuffed mofongo entrees are the real specialty here, offering options like chicken, shrimp, pork, skirt steak, and Creole-style mahi-mahi. If you want hearty fare, the chicken or shrimp asopao is another option. The coconut flan and guava cheesecake do not disappoint.

Had your fill of history? Then, check out the shopping district on lower Cristo Street and San Francisco Street. You’ll find boutiques selling fine art and folk art, and for tourists—all sorts of funky souvenirs, knickknacks and handcrafted items from Puerto Rico and across the hemisphere.

Old San Juan is a great place to shop for jewelry, with several stores selling the world’s best brands at competitive prices. Most shops are also located in the shopping district around Cristo and Fortaleza streets. There are many shops selling some of the world’s best brands in jewelry at competitive prices.

Art lovers will also be able to visit several galleries and antique shops with original works for sale along the Cristo Street and Fortaleza Street shopping area.

Across from El Patio de Sam, you’ll find a treasure of iconic masterpieces at Puerto Rico’s National Gallery in Plaza San Jose. The collection contains many images that are part of Puerto Rican national psyche, such as Rafael Tufiño’s Goyita and Rafael Frade’s Pan Nuestro. The island’s rich history in visual speaks volumes about its place in time and space as one of world’s remaining colonies, where an image is worth a thousand words.

Nearby is the Museo de las Americas, which showcases artisans from across the hemisphere, make sure to see the permanent collection of “Puerto Rican Santos,” wood carved sculptures of saints and the Indigenous Peoples off the Americas exhibit. The museum is located in a restored military barracks.

Old San Juan has a few great tapas restaurants (delicious Spanish and Mediterranean appetizers with local Creole flourishing, from spicy potatoes to shrimp in garlic sauce, Spanish flatbread pizza to creations like sweet veal meatballs.) It’s the perfect type of meal to linger over in a gorgeous setting.

Direct flights from the Northeast to San Juan take about three and a half hours. Luis Muñoz Marin International Airport is served by most major airlines. Old San Juan is about 15 minute taxi ride from the airport, depending on traffic. If you stay in the Old City, you will not need a rental car.

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