Puerto Rico Smart Splurges

Puerto Rico’s largest resort is located near El Yunque rainforest and sprawls across 500 acres atop a 300-foot bluff – a funicular descends to the sea where a catamaran shuttles guests eight minutes to a private island with a small beach. The property encompasses four “villages” with 750 rooms on different levels of the hill, plus Las Casitas, a hotel-within-the-hotel offering 154 luxury villas. But most of the action takes place at the top level, home to the outsized lobby, casino, tennis, 18-hole golf, a multi-level pool area and extended convention facilities. With more than a dozen restaurants, there are plenty of dining choices, though most of it skews expensive. The Asian-themed Golden Door Spa is one of the Caribbean’s most renowned.

Nestled in the heart of Old San Juan, across the street from the oldest cathedral in the Americas (first built in the 1520s), this 17th-century former convent has been reborn as a 58-room luxury hotel. Today this charming getaway fills four floors of the restored building, a portion of which surrounds an elegant courtyard with restaurants. Rooms vary in size (standard berths are a bit small), with handcrafted wrought iron pieces, mahogany furniture, exposed wooden beams, and private balconies – some offering bay views. A rooftop plunge pool helps make up for the sand-free location, though beach and pool privileges are available at Isla Verde Beach Resort, 20 minutes away by car.

Set on four hillside acres that descend gracefully to the sea, this 39-suite Spanish-Mediterranean-style inn is Puerto Rico’s most luxurious hotel. A quiet lobby sets the tone with antique bird cages containing real birds and ornate 19th-century light fixtures. But the rooms, lavish havens that invite guests to hide out for a few days, are the chief selling point – with enormous marble bathrooms and footed tubs, private gardens (or expansive decks overlooking the sea), and personal plunge pools that are wide and deep. Another plus: The inn’s Relais and Chateaux alliance assures fine dining at its esteemed (and très cher) French restaurant. The beach here isn’t great, but the pool is a lovely oasis. And although you’ll find tennis onsite and other activities nearby, this isn’t a place for restless types – the villa suites are notably devoid of distractions (like televisions and phones) that might otherwise disturb your shelter. If you can’t live without your electronic toys, book a room in the residence suites, which aren’t quite so restrictive.

Although the Saturday night scene of elite Sanjuaneros dressed to the nines doing the paseo (promenade) through the entry lacks some of the old panache, the El San Juan Hotel still has the prettiest lobby in the Caribbean. Miles of carved mahogany line the walls and ceilings, a decadent 5,000-piece crystal chandelier hovers like a spaceship over the Oval Bar, and a discrete cigar bar and elegant casino are just beyond. San Juan’s classic hotel benefited from some luxury upgrades in December 2006; rooms now boast bright modern accents like contemporary lamps, paintings in bathrooms, and white linens (as opposed to the faded tropical prints you see everywhere else). Even if you can’t afford a room, drop by and experience the casino and disco.

The elegant, comprehensive museum is worth the drive to the west side of the city. The permanent collection highlights local artists ranging from the 18th-century to contemporary; you’ll also find a five-acre sculpture garden, children’s interactive gallery, and smart gift shop. A meal at Pikayo, chef Wilo Benet’s on-site restaurant, will show diners all that Criollo (Spanish for Creole) cuisine can be. Also nearby is the Museo de Arte Contemporáneo, a collection showcasing modern works from Latin artists throughout the Americas.

Located 22 miles west of San Juan, the Rockefeller-built, Hyatt-flagged resorts are closed, but the four golf courses by Robert Trent Jones, Sr. are still the most beloved on the island. The East and West courses are probably the most demanding, while Sugarcane dishes out wind and water hazards. Hit a lousy shot and you might have to pay for Chi Chi Rodriguez’ window (he has a home there).

Located near Fajardo, the El Conquistador’s course is known for steep climbs and breathtaking views of the ocean and rainforest.

Charter a shore or boat dive from San Juan to explore Caribbean marine life like grouper, butterfly fish, arrow crabs and—if you’re lucky—sea turtles.

Chef Roberto Treviño serves up island-fresh seafood, oysters and creative ceviche dishes...more

Get your jam on at this Reggaetón hotspot in the heart of Old San Juan—it is the place to bump and grind the night away.