Puerto Rico's sun-kissed capital of San Juan is more than just a jumping-off point for the island’s many beaches. This thriving metropolis is worth an extended visit, thanks to its vibrant culture, culinary prowess, and hot nightlife. Relatively small, San Juan is an all-hours urban playground pairing the best of Latin America and North America.
Splurge: Olive Boutique – Set just off Avenida Ashford in the upscale Condado district, the Olive Boutique is a 15-room hotel on a residential street just steps from the lagoon. The owners were inspired by their travels in the Mediterranean, and the aptly named Olive reflects those voyages.
The lobby, hallways, and ground-floor restaurant overflow with regional furniture and artifacts. The best bets are the spacious Mediterranean suites, with their mod-Provencal aesthetics and glass-box bathrooms. (Some even have prime lagoon views.) After dinner at Olivia, the hotel’s restaurant, head up to the private rooftop club (membership is required if you’re not a hotel guest), where you’ll find cozy cabanas, a roaring fire pit, and a pair of steamy Jacuzzi tubs. Doubles from $279.
Steal: Da’ House Hotel – Leave it to a band of musicians and artists to open a hotel that’s both funky and affordable. Da’ House evokes Europe with 30 rooms spread over four floors in a restored building that once housed the Centro Nacional de las Artes. Each room, though small, is quirkily designed with original black-and-white tile floors, sturdy wooden furnishings, and colorful local art. Anchoring it all is a central “hangout” room — along with poetry and music at the iconic Nuyorican Cafe on the ground floor. Doubles from $80.
Tip: Although Condado may be considered San Juan's busiest district, its beaches leave much to be desired. Consider one of the small-scale boutique hotels or bed-and-breakfasts in nearby Ocean Park, whose wide swath of sandy, palm-limed shores is where sun-loving locals flock each weekend.
Breakfast: Kasalta – This classic café, in the residential district of Santurce, is packed each morning with locals hungry for traditional island fare. Start the day with a hefty pressed breakfast sandwich, or come later for thick empanadas, tres leches cakes, or rich flan.
Lunch: Cafe Tresbe – A dose of Los Angeles cool in the heart of Santurce, Tresbe is an open-air eatery operating out of a repurposed shipping container. Set on a busy corner, with al fresco tables shaded by oversized orange parasols and thatched palapas, Tresbe serves a modern, pan-Latin menu. Expect perfect fish tacos and ultra-fresh ceviche, accompanied by freshly made hot sauces sweetened with mango and papaya.
Dinner: 1919 Restaurant – The Condado Vanderbilt Hotel is a Spanish-revival landmark in the midst of a five-year renovation set to be completed in 2014. Already open, however, is 1919 Restaurant, which takes its name from the year the hotel debuted. Michelin-starred Chef Juan Jose Cuevas — a native son who made his mark in New York City before returning to oversee 1919 — created a global menu inspired by the organic ingredients he sources from small-scale farms.
Dessert: Koco – Koco is among the latest outposts opened by restaurateur Emilio Figueroa, who established San Juan’s Old City as a hub of culinary ingenuity. As its name suggests, coconuts appear everywhere — from the coconut mojito to an indulgent brownie sundae with coconut ice cream.
Tip: Old San Juan’s most exciting culinary arrival is Mercado Agricola Natural, the weekly organic farmers market, held on Saturdays from 8 am to 1 pm. The mercado — which is held in the plaza of the colonial-era Museo de San Juan — lures two dozen vendors offering just-picked produce, fresh pastries, and artisan cheeses. The crowd of locals includes a fair number of top San Juan chefs.
For everyone: El Morro – Located at the northwestern-most tip of Old San Juan, Castillo San Felipe del Morro — commonly known as “El Morro” — is a 16th-century citadel and the city’s most iconic historic monument. A UNESCO World Heritage Site, El Morro is one of the most conspicuous symbols of Spain’s colonial glory and an instant retreat to an era of explorers and pirates.
For families: Balneario El Escambron – Of all San Juan’s beaches, Escambron is the nearest to the Old City. Shrouded by palms and anchored by a wide slab of sandy shore, Escambron is popular both for a family-friendly vibe and prime views of the San Cristobal and El Morro forts. Thanks to a protective coral reef, waves are relatively tame, which makes it as suitable for snorkelers as it is for sun seekers.
For couples: Casa Bacardi – Located on the southern side of the harbor, the Bacardi rum distillery dates back to the 1930s, when the Cuban Bacardi family began its Puerto Rican operation. The 17,000-square-foot “cathedral of rum” dates back to the early 1960s and is the largest premium rum factory in the world.
Bacardi fans can witness rum-making from fermentation to bottling at the distillation museum — followed by a few rounds of samples and even cocktail lessons at the art deco-styled bar. Tours last 45 minutes, and run every day except Sunday — though on Saturday, the bottling facility is closed.
For the adventurous: With its miles of sandy shoreline, San Juan is ready-made for outdoor fitness and fun. Runners looking for dedicated pathways should consider Parque Barbosa in Ocean Park, as should paddleboarders.
Tip: Just below El Morro is one of San Juan’s most beautiful — and overlooked — attractions: Santa Maria Magdalena de Pazzia Cemetery, which dates back to 1863 and faces the sea. Although somewhat neglected, the cemetery is filled with ornate marble tombs and grand crypts laid out in tidy fashion along pedestrian-friendly pathways.
Although they may not have the reputation of their Cuban counterparts, Puerto Rican cigars are unquestionably world-class. Shop for the best at the aptly named Cigar House, which offers cult labels such as Oliva and Camacho. The choicest stogies are kept in jewel-like humidors at Cigar House’s original boutique.