SAN JUAN, Puerto Rico — When you think of places in the United States with great design and a flourishing art scene, you might imagine Los Angeles, Miami, or New York, though not necessarily San Juan, Puerto Rico. Which is too bad, because in recent years, the U.S. Territory has emerged as an epicenter and creative home base for many artists, designers, and hoteliers. Beyond the postcard beaches, resorts, and palm-lined streets, a close-knit creative community is creating, collaborating, and demonstrating a spirited resilience. And doing so despite the island's frequent tensions with the American government, internal financial issues, and its vulnerable location in the Atlantic where the eyes of twin hurricanes Irma and Maria brought destructive havoc in 2017. As they've proven again and again, Puerto Ricans know how to rebuild anew and emerge with strength.
Loisse Herger and Fernando Davila, the founders behind O:LV Fifty Five and O:Live hotels in Condado, the buzziest neighborhood in San Juan, are leaders in Puerto Rico's creative renaissance. As first-time hoteliers, the husband and wife team continuously find the silver lining in the wake of any storm, taking advantage of the opportunity to start anew. When 160-mile per hour winds from Hurricane Maria barreled over the island, the couple spent the storm caring for their guests at O:Live and providing food and water for neighbors in need. At the time, they were months away from opening their second property, O:LV Fifty Five, which emerged unscathed from the storm. They were committed to supporting the local community and helping restore the island and its resources, and made great strides through their food and beverage program. Because destructive winds had flattened the landscape and destroyed nearly all crops on the island, most hotels were outsourcing from the United States, taking business away from local farmers. But Herger and Davila, along with the hotel group's chef, Mario Pagan, instead worked with local farmers and utilized the resources that were available, serving Puerto Rican comfort food and the best of the island's surf and turf. And while the island has continued its recovery in the past four years, Pagan has maintained those relationships with farmers, infusing his global dishes with Puerto Rican flavors.
Discerning travelers themselves, Herger and Davila go against the grain of a relaxed island resort vibe, adding a dose of glamour to their hotels, which are both located on the serene Condado Lagoon. Fifteen-room O:Live takes inspiration from the Mediterranean (a rustic farmhouse style, lots of reclaimed wood) and Old San Juan (pastel-colored terraces and wrought-iron balconies). At O:LV Fifty Five, they immerse guests in a minimalist city vibe, using lots of marble, sleek crisp lines, moody interiors, floor-to-ceiling windows, and large balconies in each of the 26 rooms with views of the lagoon. The impressive rooftop overlooks downtown San Juan on one side and the Caribbean waters on the other.
Many Americans underestimate Puerto Rico as an easy, no-passport-required Caribbean destination. That's a mistake Herger and Davila are helping to correct by showcasing the creative design and spirit of the island — one that is constantly able to reinvent itself through the strength of the local community. Which makes O:LV Fifty Five an ideal home base for exploring San Juan's emerging design scene.
Checking In at OLV: Fifty Five
Location: Sandwiched between the lagoon and the beach in the chic Condado neighborhood.
Style: Rather than follow a barefoot beach vibe like their neighbors, the hotel punches up the glam, with jewel-toned velvet furniture, marble floors, gold-dripping chandeliers above plush beds, gilded rain showers, and a lobby with moody dark walls and brass statues.
Feel-Good Factor: The hotel is actively involved in the preservation of the lagoon, hosting several volunteer clean-up programs throughout the year, as well as community groups and fundraisers for the cause.
Standout Detail: You won't find another rooftop in Condado quite like this. The elevators open onto a 1977 Rolls Royce that has been converted into a DJ booth and champagne bar with a swanky indoor lounge. Outside, bi-level decks show off a sparkly, marble infinity pool fringed by lounge chairs — cocktails are, of course, at the ready. Upstairs, a colorfully illuminated jacuzzi overlooks the turquoise waters of the lagoon on one side and the Atlantic on the other. The sunsets are spectacular.
This Place Is Perfect For: Stylish couples who want a romantic, glitzy getaway and to explore the up-and-coming design scene. Also those who love the idea of the beach...but would rather lounge by the pool.
But Not So Perfect For: Leave the kiddos at home, as the hotel is strictly adults only.
Food & Drink: Along with the rooftop, another star of the show is local celebrity chef Mario Pagan's Asian-Caribbean fusion restaurant, Raya. His plating and culinary design matches the hotel's flashy aesthetic: bright edible flowers and dollops of colorful spiced sauces accent unusual pairings like wasabi grilled cheese and beet matcha ice cream cookies. Green velvet banquets are arranged beneath floor-to-ceiling gilded mirrors, with Art Deco-inspired marble floors, and a large bar where guests are encouraged to get acquainted with the all-star bartenders happy to share their great knowledge of sake and whiskey cocktails.
Rooms: The glamour continues upstairs in 26 suites, all but two of which have a spacious balcony overlooking the serene lagoon. (Keep an eye out for manatees!) Sun beds are positioned directly outside the indoor/outdoor shower to rinse off after a mid-morning swim.
Activities: Reserve a day on the Champagne floating deck on the Condado Lagoon. (Can you tell the hotel loves any excuse to pop some bubbly?) They'll have private bean bags chairs, a picnic basket filled with fresh cheese, fruit, and chilled wine waiting. The hotel also partners with nearby Aqua Fitness for standup paddle board yoga, pedal boarding, and kayaking on the lagoon.
The beauty of San Juan is not only its proximity to the United States (a four-hour flight from NYC) but also the small island vibe that lets visitors soak up much more than sunshine in a short amount of time. Since cruise ships aren't sailing right now, Old San Juan, which is normally a highly trafficked port, is wonderfully free of day-tripping tourist hordes. (If only it could stay this way.) This is a perfect time to explore the beautiful beaches and nearby islands, historic forts, to shop along the cobblestone streets, and to salsa dance until the wee hours of the night.
From OLV: Fifty Five, it's a short walk across Ashford Avenue to Condado Beach. Framed by a string of high-rise hotels and resort complexes, it's not private or remote by any means, but it is ground zero for water sports and beachfront bars. For a day offshore, hire a boat from Fajardo to Culebra island, where the mile-long horseshoe-shaped bay of Flamenco Beach is all shallow turquoise waters, white sands, and vibrant coral reefs teeming with marine life. From there, the outlying islands Culebrita and Cayo Luis Peńa can be easily accessed on kayak from and are great for diving offshore Playa Carlos Rosario and Playa Tamarindo.
Santurce, just south of Condado, is San Juan's version of Miami's Wynwood Arts District — a beautification project of old and abandoned buildings covered in large, colorful murals of surreal dreamscapes by local artists and contemporary museums. During the days and nights of the annual festivals Santurce es Ley and Los Muros Hablan, street artists do live painting and the streets are filled with locals dancing. Museo de Arte del Puerto Rico is spread across a 130,000-square-foot property, with eighteen exhibition halls of paintings, sculptures, and carvings by Puerto Rican artists from the 17th century to today an an on-site botanical sculpture garden that hosts outdoor concerts. Sister museum Museo de Arte Contemporáneo (aka the Mac) showcases multidisciplinary works from Caribbean and Latin American perspectives.
To see the best of the island's unique architecture design, spend an afternoon winding through Old San Juan's cobblestone streets, where music blankets the ornate wrought-iron balconies and pastel-colored buildings that still bear traces of the Spanish colonists who discovered the Caribbean island in the 16th century and were influenced by Gothic and Baroque architecture. Even if you're not a history buff, the hilltop 16th-century forts El Morro and San Cristóbal are impressive for their crumbled stone walls and views of the Atlantic.
Ashford Avenue, the main drag along Condado Beach, is the Rodeo Drive of Puerto Rico: blocks of tacky souvenir shops and high-end boutiques ready for itchy wallets. A better plan: Go a few blocks south and inland to boutiques run by eco-conscious locals selling beachwear, artisanal home goods, vintage jewelry, and sustainable designer pop ups. Love Is You & Me, T Playa, and Playero are within a few blocks of the hotel. El Mercado Libre is the pop-up market in Santurce where you'll find locally made goods like hot sauces, baked goods, skin-care products, and a cool event space with frequent yoga workshops and music events.
If you can't get enough of chef Pagan's cooking, head to his other restaurants, Mario Pagan and Sage, the Mediterranean-inspired steakhouse with a vibrant rooftop bar for cocktails and aperitif at O:Live. Right off Calle Canals, Santaella brings a warehouse feel to the tropics with reclaimed wood and exposed brick centered around an interior garden. Dishes incorporate vibrant local produce, and the signature cocktail, a macerated watermelon mojito, is pure island life in one sip.
A sense of mischief permeates the city's vibrant nightlife scene, at its best in Old San Juan and Santurce. El Batey on Calle Cristo in Old San Juan is an infamous seedy dive bar with walls covered in scraggly signatures and graffiti left by decades of patrons, including Hunter S. Thompson, who salutes the bar in his novel, The Rum Diary. It's the last remaining bastion of the blurry 1960s San Juan bar culture, where The Rolling Stones shared a few rounds of Cuba Libres and billiards with the weathered bartender. Today, warm sea breezes ripple through the dusty fan circling overhead, beers cost $2, and the juke box rattles vinyl 45s.
If umbrella-topped cocktails are more your style, have a piña colada at its alleged birthplace, Barrachina. A couple of those, and you'll be heading to La Factoría, the coolest speakeasy in the neighborhood with a "choose-your-own-dance ability" maze of rooms. A sophisticated cocktail bar leads to a sweaty salsa room, then rotating DJs, and beyond. For more live music, head to La Placita in Santurce, a marketplace by day and outdoor dance hall at night. La Terreza de Bonanza hosts weekly performances of the classic Puerto Rican dance styles, pleneros and bomberos, on the small outdoor terrace.