Stroll the beach at the Conrad San Juan Condado Plaza

The Cosmopolitan Island

Puerto Rico has a diverse portfolio of natural assets, including the famous rain-forest preserve El Yunque, the coffee growing highlands, the dry desert southwest, and the surf-strafed west coast. Having road-tripped several times around the island, I’ve seen them all. Yet even when I’ve driven the most rutted-out road, dodging stray chickens and near collisions in the mountains; emerged from a remote hike that involved fording a river in the rain forest; or swum a channel to reach a mangrove barrier island, I’ve found a party going on — a roadside pork roast, a beachfront barbecue, and a family reunion, respectively.

Stroll the beach at the Conrad San Juan Condado Plaza
Of the over 7,000 islands in the Caribbean, Puerto Rico loves to celebrate. It’s loud, colorful, and highly convivial. Just try dining solo, as I did last summer at the hot new tapas restaurant Bar Gitano from locally acclaimed chef Roberto Treviño. Instead of blending into the woodwork, I drew stares. “Puerto Ricans just want to make sure everyone is having a good time,” explained a woman dining with her husband next to me. “If you are alone, they think something is wrong.”

Sometimes you want seclusion, and sometimes you want social. For the latter there’s San Juan, metropolis of the Caribbean, home to more than 440,000 people, a spicy restaurant scene, buzzy nightclubs, and busy beaches filled with merrymakers both local and not.

“I believe Puerto Rico could be the next Miami,” says Shimmy McHugh, who runs several successful nightclubs in San Juan including Eternal lobby lounge in the Conrad San Juan Condado Plaza. “There’s no shame in drinking every night of the week, and lunch can go right into dinner.”

Visit a waterfall at El Yunque
It’s one-stop dining for a pair of new restaurants from the island’s top celebrity chef, Wilo Benet, at the newly updated Conrad San Juan Condado Plaza. Designer David Rockwell’s firm gave the 570-room mid-century modern hotel a renovation a couple of years ago, resulting in a whitewashed lobby with circular pink banquettes and globe light fixtures. Last year, Benet moved his flagship fine dining restaurant, Pikayo, into the hotel and later opened the new rotisserie-focused Varita for casual, hearty fare in a street-level room splashed with colorful paintings and neon-washed photographs by the chef-turned-artist.

Just east of Old San Juan, Condado has emerged as the chic shoreside strip for dining — Bar Gitano, for example, is here — and shopping (think Cartier, Louis Vuitton, et al). Among design and nightlife draws, the recently renovated La Concha, A Renaissance Resort houses restaurant Perla in a clam-shaped room of 1958 vintage, serving, appropriately, seafood with a modern focus.

Sleep at the W Retreat & Spa-Vieques Island
La Concha’s trendy Lobby Bar parties into the wee hours on weekends. But any night of the week is a scene in the lobby of the 386-room El San Juan Hotel & Casino, The Waldorf Astoria Collection further down the shore in the neighboring Isla Verde area. Under a vast crystal chandelier, the bar buzzes with activity as the central hub between satellite restaurants, nightclubs, and casino. A recent room renovation and new beach club, including a just-opened Burger Bar, have infused the historic property with new life beyond the lobby too.

Not to be outshone, its neighbor down the shore, The Ritz-Carlton, San Juan, houses a branch of the luxe Il Mulino steak house, newly offering wine pairing dinners, and the luscious BLT Steak. The new eco-ritual in the spa gets you beach-body ready with a brush, polish, wrap, and massage using organic products.

To date, Puerto Rico’s sense of glamour has been highly urban, with a few discrete getaways, like the Horned Dorset Primavera on the west coast, with 39 suites that draw couples away from the capital for quieter respites. But with the November opening of the 139-room St. Regis Bahia Beach, the island will get its first ultraluxury hideaway, one that manages to combine residential repose with unspoiled nature. The 483-acre property, given the green thumbs-up by Audubon International, offers views of El Yunque inland from two miles of private beach and several of the Robert Trent Jones, Jr.-designed fairways on the 18-hole golf course. The resort, 16 miles east of San Juan’s airport, offers enough on-property stimulation to keep guests from missing the capital, including a 10,000-square-foot spa featuring massage villas with private outdoor terraces, more than seven miles of walking trails, kayak tours through its rivers, and Fern restaurant from famed chef Jean-Georges Vongerichten.

Swim in El San Juan Hotel & Casino’s pool
When islanders escape for the weekend, their frequent go-to spot lies just eight miles offshore in quiet Vieques, upscaled earlier this year with the opening of the 157-room W Retreat & Spa-Vieques Island. The resort balances low-key chic — including a banquette-ringed bonfire pit, outdoor massage tables, and oceanfront yoga — with a pinch of glamour provided by Mix, a spinoff of the popular Las Vegas restaurant from Michelin-starred chef Alain Ducasse. It’s still Puerto Rico, after all.

Conrad San Juan Condado Plaza

Horned Dorset Primavera

St. Regis Bahia Beach

The Ritz-Carlton, San Juan

W Retreat & Spa-Vieques Island

Bar Gitano
(787) 294-5513


Pikayo and Varita

Lobby bar, El San Juan Hotel & Casino
(The Waldorf Astoria Collection)

Lobby Bar, La Concha
(A Renaissance Resort)

Puerto Rico Tourism Company