Slumber Party: Where to Sleep & Play in San Juan

With no passport required, sexy San Juan is a convenient east coast destination for a holiday weekend or longer winter getaway. A contrast between Old World and 21st century, three luxurious, LGBT-friendly hotels offer unique amenities for tourists who want more than a bar and beach access.

What's Old is New Again
After 252 years as a Carmelite convent, the historic Old San Juan property that eventually became the Hotel El Convento closed in 1903. The former convent spent decades in decline - an architectural soap opera - as a retail store, dance hall, flophouse and parking lot. Rescued from oblivion by the Woolworth family, it reopened in 1962 as a luxury hotel with mahogany beams and rugs hand woven in Grenada. Restaurants, meeting rooms and other amenities were added in the 1990s.

A destination long popular with the jet set, El Convento's colonial-style rooms and public spaces reek of old-money quality, despite smallish bathrooms and a few charming signs of age. Featured in Architectural Digest and Conde Nast Traveler, it's a national historic landmark.

El Convento's El Picoteo is a favorite for tapas and cocktails, while acclaimed Chef Luis Castillo has created a menu infused with vegetables and herbs (grown on the roof!) for his tranquil outdoor restaurant Patio del Nispero. Tuna with passion fruit escabeche and wagyu beef cheeks were standouts at a recent six-course meal. For breakfast, try the cornmeal with cinnamon; it's a local specialty and a nice riff on grits.

Salon Martorell is the standout among several meeting/banquet rooms, featuring paintings and quirky original light fixtures created by San Juan artist Antonio Martorell, a frequent visitor to the hotel. And make time for Trixie, a surprisingly agile calico who enjoys attention from tourists and run of the hotel.

Luxury with a Moderns 60s Feel
From the charm of the past to the best of today, Algonquin Hotel-style mascots would be out of place at the beachfront La Concha Resort, a short drive from Old Town in the modern city's Condado neighborhood.

Designed by local architects Osvaldo Toro and Miguel Ferrer, the fa�ade and lobby of this 4-star property have a 1960s Palm Springs feel. It's sleek, white and modern throughout, except for a decidedly unglamorous casino tucked in a corner just off the lobby. The ocean is warm, the small beach well maintained and the beach and pool service excellent.

With its distinctive seashell shape, La Concha's Perla restaurant is an architectural delight, surrounded by pools and lit by murano "artichoke" lamps. Black Tea Infused Pork Tenderloin, Snapper "Colirubia" with Octopus Creole Sauce and a range of other fish and seafood options make choosing a challenge.

The resort's signature cocktail menu is also tempting. Beware the irresistible Concha Mule; a tasty mix of Ketel One, ginger syrup and lime juice, it's hard to stop at one.

Hobnobbing at the Vanderbilt
Be sure to explore the neighboring five-star Condado Vanderbilt next door - a luxurious sea of marble with a larger beach and even more pools. A day at the Vanderbilt can include spa treatments, a farm-to-table lunch and an afternoon in the sun.

The Vanderbilt's luxurious spa features a full spa menu (a wonderful, recuperative massage helped process the previous night's mules), highlighted by the exotic Hamman, a treatment common in North Africa, which "combines ancient rituals and modern techniques."

Under the direction of Chef Juan Jose Cuevas, The Vanderbilt's elegant Tacos & Tequila-belying its cheeky strip mall name-features delicious, locally sourced guacamole (Puerto Rican avocados are juicier), queso, goat cheese quesadillas and jalapeno margaritas with black pepper, made from local tequila.

San Juan is consistently hot, but the fall/winter sun sets early. Spend the afternoon escaping the shade as you migrate from one luxurious pool to another, and eventually end your journey in the sun at the expansive space just off the Vanderbilt's lobby, with an infinity pool, DJ and ocean views.

Getting Hitched
All three featured hotels are popular locations for same-sex weddings and honeymoons-on Saturday night a smiling girl-girl wedding couple walked through the La Concha lobby, as if on queue. La Concha, which markets to the community, hosts about 15 LGBTQ weddings and countless elopements every year, says JC Cappas, the property's charming LGBT liaison. Marketing materials even feature JC and his husband, who held a post-wedding photo shoot in La Concha's Presidential Suite.

If you're trying to choose a winter getaway or wedding destination, all of these high-end properties offer genuine value. If you gravitate toward historical sites and boutique hotels, consider El Convento. A South Beach fan? La Concha is probably for you. The Vanderbilt, built in 1919, but completely renovated, might be "just right' if you're a sun lover who falls somewhere in the middle.