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Perhaps the easiest Caribbean destination to get to—there are non-stops from an array of U.S. cities and there’s no need for a passport—this lively, late-night-loving city makes for a breezy and affordable couple’s escape if the romance you crave is more sizzling than sedate. Still, where you stay in San Juan will have a major impact on the kind of experience you have. Here’s the scoop on three top tourist areas:
Condado This upscale neighborhood, flanked by a golden beach and linked to Old San Juan by the Dos Hermanos Bridge, is ideal for couples seeking a mix of sun, fun and easy access to historic sights with a little high-end shopping thrown in. All this is easily yours if you stay along resort- and boutique-lined Ashford Avenue. Two great options: the San Juan Marriott Resort & Stellaris Casino, where 525 recently renovated rooms and suites feature buttery décor and extra-large step-down balconies (splurge on an Oceanfront), the Ristorante Tuscany serves exquisitely prepared Italian specialties, and the lobby lounge outside the bustling casino becomes salsa central after 10:00PM (from $245), and La Concha: A Renaissance Resort, where the vibe flips 180-degrees toward twentysomething Latino chic, with 248 contemporary rooms towering above a stunning retro-urban architectural showpiece that feels plucked from South Beach, a lushly landscaped pool, and the sea-shell-shaped floating restaurant Perla (from $289).
Isla Verde If you want to be on the beach within minutes of landing and stay there without doing a lot of sightseeing (taxis to Old San Juan will run $20-$25 one-way), this narrow strip of resort-lined beach adjacent to the airport (jet noise can be an issue outside but sound-proofing means rooms are quiet) is a great option. Resorts are located close to each other, so you can stay at one and enjoy an easy walk to play and dine at others. Two suggestions: The Ritz-Carlton, San Juan, the city’s most elegant and upscale resort, features 416 serene rooms and suites (best bet: a Balcony Ocean View Room), a Spa with a couples suite and a co-ed sauna and whirlpool, and outposts of famed Big Apple eateries Il Mulino New York, for Abruzzi-inspired Italian, and BLT Steak, for chef Laurent Tourondel’s take on a steakhouse/bistro (from $369); and the InterContinental San Juan Resort & Casino, which features 402 recently remodeled rooms and suites with ultra-comfy beds (but tiny balconies), a lush pool area with a extra-large Jacuzzi, an intimate spa with two couples areas, and a low-key vibe but with the lavish décor and lively nightlife of neighboring El San Juan Resort & Casino just a five-minute walk away (from $199).
Old San Juan Couples who love to explore on foot and would rather spend their days sightseeing and their nights savoring San Juan’s flavor should consider a stay in the atmospheric historic heart of the city. You’ll trade the sand for shopping (don’t miss the Coach and Polo Ralph Lauren outlets) and strolling (take your camera along for your walk along the scenic Paseo de Princesa) as well as bountiful dining on everything from fine Italian at Il Perugino to trendy Latin-Asian fusion at Dragonfly to touristy but satisfying mofongo (mashed fried plantains) at Raices. Stay at Hotel El Convento, a magically romantic 58-room gem (opt for a Queen Vista since some Superior and Deluxe rooms are snug) that was originally a 17th-century Carmelite convent and is now showcase for beautifully restored Spanish-Colonial architecture (from $213).
For more trip-planning information, see our San Juan Travel Guide.