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How to Spend 72 Hours in San Juan, Puerto Rico

David Jefferys
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How to Spend 72 Hours in San Juan, Puerto Rico

Puerto Rico's largest city is well on the road to recovery after the storms of 2017.

On September 20, 2017, Puerto Rico was among the hardest hit by Hurricane Maria. The road from emergency recovery to rehabilitation was steep and long—including an island-wide blackout that seemed to last forever. Six months after the worst storm to hit the island in 85 years, we're happy to report that San Juan—the colorful, vibrant metropolis at the heart of the Caribbean—beats on. There are now 80-plus daily flights to the island (with Luis Muñoz Marín International Airport being the best served), and 121 hotels are open along with nearly 4,000 restaurants. We here at Traveler have been asked, frequently, how people can help with recovery efforts in the region. In turn, we've been told by islanders, tourism professionals, and returning travelers to—quite simply—go. Show up. Spend your vacation dollars, drink, eat, shop, and enjoy yourself. Tourism is one of the major contributors to economic success and long-term recovery. San Juan is back up and running and the popular beach and surf town of Rincon has power. Consider a long weekend not far from home. Be forewarned: You won't be losing any weight!

Day One: Cobblestones, Forts, and Cafés

Old San Juan is considered one of the best-preserved examples of Spanish Colonial architecture. Brightly painted buildings, many with flower-filled balconies, line cobblestone streets; it's the kind of photo opp that births Caribbean stereotypes, in a good way. This part of town occupies a narrow headland at the tip of a island sheltering San Juan Bay, and is capped off by the magnificent Castillo San Felipe del Morro, one of the oldest and largest Spanish-built forts in the New World. The six-level mammoth, with 140-foot tall walls, some 15 feet thick, fended off invasions by both the British and the Dutch in the 16th and 17th centuries. Castillo San Cristóbal, a sister fortification, began construction in 1765. Both are worth at least a few hours of exploration; a walk along the top of La Muralla (the ramparts) comes with terrific views out across the foreboding Atlantic. Weekend picnics are a big deal for Puerto Ricans, congregating in open fields under a sky full of kites. Don't miss the Moorish gardens at the imposing La Fortaleza mansion (also known as El Palacio de Santa Catalina, the oldest governor's mansion in the Western Hemisphere and original fort for the city, built in 1533).

If you've set out early in the day and are looking for breakfast or lunch, Café Manolín, a 1950s institution at 251 Calle San Justo, is a frozen-in-time diner serving simple Creole food to a mix of locals and visitors. As far as basic places to rest and refuel (especially in the midday heat), grab a cooling ice-pop made from tropical fruits at Señor Paleta at 153 Calle Tetuan, or a pick-me-up of locally grown and roasted coffee at Café Cuatro Sombras at 259 Calle Recinto Sur. If the day is winding down and cocktails are calling, La Factoria is a quirky and playful, deeply red-hued speakeasy at 148 Calle San Sebastián. Don't forget to pop in to the cleverly curated Pure Soul Boutique at 258 Calle San Justo for his and her clothing picks and housewares.

Checking In

The El Convento Hotel, a converted convent dating back to the 1600s at 100 Calle del Cristo, is an atmospheric option for extending a visit to Old San Juan, and its rooftop plunge pool can't be beat for a sunset dip. Larger, more resort-oriented places to spend the night can be found along the beach in the tony Condado district. The Renaissance La Concha Renaissance Resort has cheerful rooms with sea-view balconies, a handful of beautiful swimming pools, and an attractive Sixties vibe. Next door, the Condado Vanderbilt Hotel is more sedate, and attracts a refined crowd. Even if not staying here, dinner at the Michelin-starred chef Juan Jose Cuevas Soto's 1919 Restaurant shouldn't be missed. Surrender to Juan's kitchen for a tasting menu that relies predominantly on native ingredients, especially local fish and vegetables used in Puerto Rico's simple country kitchens, or fondas, and paired beautifully with a variety of wines. The O:live Boutique Hotel, one of the first of its kind in the city, retains a vaguely industrial flair with a killer rooftop bar for a nightcap and views of the Condado Lagoon and twinkling lights of surrounding high-rise apartments—a welcome sight.

Castillo San Felipe Del Morro, Old San Juan, Puerto Rico

Castillo San Felipe de Morro, Old San Juan.
Getty

Day Two: Graffiti, Shopping, and Late-Night Bites

Due south of Condado and Old San Juan, on either side of one of the city's busiest arteries, Expreso 26, are the art-and-nightlife-driven corridors of Santurce and Loíza. Streets are filled with graffiti art, small design shops, and dozens of restaurants. The area of La Placita comes to life after dark with partying folk spilling out onto the streets. Both areas are typically gritty, but they're also safe and easily walkable. It's best to break up any exploration with a visit to the peaceful sculpture garden at the celebrated Museo de Arte de Puerto Rico, considered by many to be the finest collection of modern and contemporary art in the Caribbean. The Plaza del Mercado, heart of La Placita and a still-working indoor food market, is well worth a moment or two out of the sun. Turn down almost any street in Santurce and you'll be spoiled for choices of where to eat and drink. The tiny Jose Enrique restaurant (176 Calle Duffaut, no reservations, open Monday through Saturday 11:30 a.m. to around 10 p.m.) is one of the hottest tickets in town with a menu of highly inventive modern Puerto Rican food. For a guaranteed table in a super sexy surrounds, Santaella is your best bet for dinner of sophisticated "cocina criolla" at 219 Calle Canals. Just down the way JungleBird, at number 254, is a deeply cheeky tiki bar owned by the same folks as La Factoria.

For those with an itch for shopping, head to Santurce POP, a collaborative design marketplace for small merchants, at 1116 Calle Ponce de Leon. Following the hurricanes, many small retailers moved locations within the city. This makes it somewhat frustrating to find what you want, and in case Google Maps isn't up to date (it's rare, but it happens), we've included addresses throughout based on our recent visit.

Just to the north, Loíza is an up-and-coming neighborhood in similar vein to Santurce, though it's closer to the water and beaches if pounding the pavement gets to be too much. Punto Medio is a charming cafe good for breakfast pastries and coffee at 1762 Calle Loíza. Unfortunately, the once-funky El Departamento de la Comida lost its building during Hurricane Maria, but the "revolutionary" owners are working to re-open as soon as possible with their creative and eco-conscious menu of all-vegan, organic, experimental food. Until then, consider checking out vegetarian-driven The Dreamcatcher inn, only steps to the beach in nearby Ocean Park. Also nearby is La Cueva del Mar, a good bet for a fresh fish taco lunch.

After a day filled with wandering, plop yourself down for a piña colada. Invented in San Juan by a bartender at the Caribe Hilton Hotel (scheduled to reopen in January 2019) in the mid-'50s, it's rumored that Joan Crawford declared the drink tasted better than slapping Bette Davis in the face. Others report it was invented in the Barrachina Restaurant in the old city. Regardless, change into respectable duds and head back to Condado for a swanky sip and dinner above the sand at Oceano on a side street perpendicular to the ocean. The ceviche and ropa vieja stand out, as do the restaurant's Miami Beach-styled takes on Puerto Rico's classic mofongo with either colossal shrimp or veggies.

Graffiti of pink woman and blue woman beaming light.

Graffiti in Loíza.
Alamy

Day Three: A National Park, High Speed Catamaran, and the Best Beaches Around

Puerto Rico's El Yunque National Forest is the only tropical rainforest in the U.S. national forest system. At 28,000 acres, it's one of the smallest but one of the most biologically diverse with hundreds of animal and plant species, many indigenous to the island. The park remains mostly closed following Hurricane Maria with only a handful of roads, trails, and sites recently reopened. That said, viewing the park from a distance is still a thrill. The jungle foliage is back in full force and rain-filled clouds still blanket the highest mountain tops. Book a day trip through East Island Excursions. They'll pick you up from a series of spots downtown, early, for the a one-hour drive east to Fajardo, passing the forest to your right. From a very fancy marina, the company operates a small fleet of sleek, high-speed catamarans to offshore islands. One of them, and the largest, Vieques, is still recovering. Culebra, on the other hand, looked as beautiful as ever on our most recent trip there a month ago. High waves and wind made the 45-minute crossing an adventure not soon to be forgotten. Views of the receding forest, gut-wrenching swells, and warm, bright blue Caribbean water splashing anyone sturdy enough to sit on the outside, stern deck. The payoff? Snorkeling off Culebra in a sheltered bay, and an afternoon of swimming and sunbathing alongside a stretch of impossibly beautiful sand on the uninhabited islet of Culebrita. East Island provides a light lunch, drinks, and snorkel gear for the day, but not sunscreen or towels. Itineraries change according to the weather, but Zoni, Flamenco, and Playa Tortuga beach stops are all equally Instagrammable and the return trip, with the current, was substantially less rollercoaster-like.

Note: If nautically challenged, you can get to Culebra in a small plane on Vieques Air Link from San Juan's inner-city airport on Isla Grande, SIG in under half an hour to CPX.

Back on terra firma, a last night in San Juan could be spent listening to the Puerto Rico Symphony Orchestra. The company has already performed a series of free concerts across the island and will be at the Centro de Bellas Artes Luis A. Ferre through early June 2018. The Casita Miramar, a restaurant that sprawls through a higgledy-piggledy collection of rooms in an old hotel near the city's convention center, serves a mean dish of shrimp-stuffed-avocado, evil but delicious pumpkin fritters, and a beyond-respectable mofongo with fresh mahi-mahi. The atmosphere, especially sitting on the outdoor upstairs terrace, is worth what is inevitably a long wait even with reservations. No pretense here, just good hearty food.

San Juan is a short flight from multiple East Coast airports, and an easy way to spend a long weekend in the sun with all of the benefits of being in a city. It has little of the pretense of South Beach, tons of charm, and a good helping of scrappiness (evident even before last year's storms).

Island of Culebra, Puerto Rico

Culebra, Puerto Rico.
Getty

With reporting by Megan Spurrell.