News & Advice

How to Spend 72 Hours in San Juan, Puerto Rico

You'll leave thinking three days is hardly enough.
Old  San Juan Puerto Rico
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While Puerto Rico is still recovering in many ways post-Hurricane Maria, the tourism numbers in the colorful, vibrant metropolis of San Juan are as high as they've been in the last decade. There are 110-plus daily flights to the island, nearly every hotel has reopened (many with major, multi-million dollar upgrades), and there's a renewed energy and sense of local pride as the island works to welcome travelers back after the post-storm slump. We've always loved the island as a quick weekend getaway—it is, after all, just a couple hours from the East Coast, and Americans can visit without a passport—and with new restaurants, bars, and experiences cropping up every month, we're hardly short on reasons to visit. If you're crunched for time, here's our favorite way to spend three days in the island's capital city. Fair warning: After just three days, you can bet on booking a return visit.

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—so expect to see families and friends congregating in the open fields under a sky full of kites. Before leaving, check out 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 get in 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. Spend your afternoon wandering the old city, and make sure you swing by the cleverly curated Pure Soul Boutique at 258 Calle San Justo for his and her clothing picks and housewares. When you need to rest and refuel (especially in the midday heat), grab an ice-pop made from tropical fruits at Señor Paleta at 153 Calle Tetuan, or a pick-me-up at Café Cuatro Sombras where all the coffee is locally grown and roasted at 259 Calle Recinto Sur. Wrap up your day at La Factoria, a quirky and playful (and very locally famous) speakeasy in the Old City, or change into respectable duds and head to Condado for a swanky sip and dinner above the sand at Oceano. 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.

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 you aren't staying at the Vanderbilt, dinner at chef Juan Jose Cuevas's elevated 1919 Restaurant shouldn't be missed. Surrender to Cueva's kitchen for a tasting menu that relies predominantly on the same native ingredients found in Puerto Rico's simple country kitchens, or fondas, especially fish and vegetables, 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 the twinkling lights of surrounding high-rise apartments.

Castillo San Felipe de Morro, Old San Juan.

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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 Loíza and Santurce. Graffiti art fills the walls here, which enclose small design shops, and dozens of restaurants. And, though both areas are typically gritty, they're also safe and easily walkable. To hit both neighborhoods in one day, start in Loiza, then move on to Santurce (there's a bit more evening activity in the latter).

Up-and-coming Loiza is closer to the water—perfect for a quick dip at the beach if pounding the pavement gets to be too much. Punto Medio is a charming café 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, although owners planto re-open in 2020 with their creative, eco-conscious and vegan menu. Until then, consider checking out the vegetarian-driven Dreamcatcher inn, just a block off the beach in nearby Ocean Park or La Cueva del Mar, a few blocks south for its fresh fish tacos.

In Santurce, make sure to visit 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. Then, swing by Santurce POP, a collaborative design marketplace for small merchants. Don't miss the indoor food market Plaza del Mercado (refuel with an alcapurria fritter or fruit smoothie), smack dab in the middle of the La Placita main square which becomes the epicenter of a lively street party at night. You'll find plenty of spots to eat for lunch and dinner just off La Placita, but Jose Enrique's eponymous restaurant (no reservations) is one of the best (and hardest to get) tables in town with a menu of highly inventive modern Puerto Rican food. For a guaranteed table in 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 cheeky tiki bar owned by the same folks as La Factoria and perfect for a drink to cap off the evening or a smaller meal—chef Paxx Caraballo Moll is there making some of the best bar food you'll find anywhere.

Graffiti in Loíza.

Alamy

Day Three: A National Park, a 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, and home to many endemic plant and animal species. Unfortunately, the park remains mostly closed following Hurricane Maria with only a handful of roads, trails, and sites recently reopened, but viewing the park from a distance is still a thrill—and a day trip to the nearby island of Culebra ensures you'll pass by.

Book a day trip with East Island Excursions, which motors a small fleet of sleek, high-speed catamarans to Culebra. They'll pick you up early from one of several spots in downtown San Juan for the a one-hour drive east to Fajardo, passing the forest on your right. High waves and wind made the 45-minute crossing an adventure not soon to be forgotten, but the payoff is worth it: Snorkeling off Culebra in a sheltered bay, and an afternoon of swimming and sunbathing alongside a stretch of beautiful sand on the uninhabited islet of Culebrita. East Island provides a light lunch, drinks, and snorkel gear for the day, but note that you'll need to bring your own sunscreen and towels. Itineraries change according to the weather, but Zoni, Flamenco, and Playa Tortuga beach stops are all equally gorgeous.

Note: If boats are not your thing, the nautically challenged 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 for just a bit more per person than the cost of the snorkeling tour.

Back on terra firma, consider spending your last night in San Juan at the Centro de Bellas Artes Luis A. Ferre. Performances over the past year have included shows like Hamilton, and Puerto Rico Symphony Orchestra concerts, and tickets can be purchased online, in advance. For dinner, 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 shrimp-stuffed-avocado, delicious pumpkin fritters, and delicious mofongo with fresh mahi-mahi. The atmosphere, especially on the outdoor upstairs terrace, is worth what is inevitably a long wait, even with reservations. No pretense here, just good hearty food—a perfect cap on a weekend chock full of the same.

Culebra, Puerto Rico.

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This story was originally published in 2018. It has been updated with new information.