1. Where to Stay
Enjoy the breeze from the rooftop lounge at Olive Boutique Hotel (from $179), an elegant, Mediterranean-inspired 15-room property in the centrally located Condado district. Ask for one of the more spacious O:Lifestyle suites, which have open-plan bathrooms, reclaimed-wood desks, and all-glass spa showers stocked with L’Occitane toiletries, not to mention Nespresso machines. The Old World-meets-modernity theme spills into the cozy restaurant, where Argentinean chef Nicolás Gomez serves updated classics like foie gras with organic pumpkin marmalade ($21) and gnocchi with pistachio pesto ($22).
Mingle with health-conscious travelers at Dreamcatcher (from $65), an intimate two-year-old guest house with a vegetarian kitchen doling out communal dinners. Everything about this inn promotes relaxation, from its location in a quiet, residential seaside neighborhood to the hammocks hanging in unexpected corners, and the flower-filled garden dotted with buddha statuettes. All ten rooms are furnished with handpicked vintage, themed pieces: pendant lanterns and kilim rugs in the Moroccan suite; built-in bookshelves painted bright green in the library. Sign up for a yoga class, held at sundown around a fragrant lemon tree, or for a paddleboard lesson taught in a nearby pond.
Take in the scenery at La Concha (from $219), a gorgeously renovated Modernist hotel originally built in the 1950s. Eye-catching period features include a seashell-shaped restaurant that appears to be floating on water and an ample brise-soleil (a sun-shading structure popularized by Le Corbusier) at the entrance, but everything else has been reinvented, starting with the expanded lobby, clad entirely in white Calacatta marble and strewn with leather wingback chairs orbiting a busy central bar. Scope out the scene while sipping a mango caipirinha ($11), then claim a chair by the two-tiered pool right outside. Request a room in the all-suite tower for perks like sun-drenched balconies, Saarinen furnishings, and direct access to another adults-only pool.
2. Where to Eat
Taste new twists on Puerto Rico’s culinary traditions at José Enrique, near the 100-year-old farmer’s market in Santurce (where many of the restaurant’s ingredients come from). The chef earned a James Beard nomination elevating old-school dishes like bistec encebollado ($22), a steak drenched in sautéed onions that he makes with ultra-juicy tenderloin, or tembleque ($8), a typically dense coconut dessert that he reimagines as a soft pudding topped with tiny cinnamon spheres that burst in your mouth. The convivial dining room fills up quickly (walk-ins only); if the wait seems too much, try out lunch at the chef’s Capital, which serves similar food in a much bigger, sleekly designed space with a Creole brasserie concept.
Drive 15 miles west for dinner at Dorado Beach, the luxe Ritz-Carlton resort where chef José Andrés recently opened Mi Casa. The design here is as ambitious as the food, with massive windows framing postcard ocean views, polished dark wood throughout, and plenty of fanciful accents, like a bespoke foosball table and three alabaster busts depicting prim ladies chewing gum and eating Popsicles. There’s humor in the menu, too: an appetizer of chicken croquetas ($14) arrives inside an acrylic sneaker designed by Sami Hayek (Salma’s brother), and yucca “churros” ($12) are accompanied by peanut-butter sauce inside a paint tube. The signature entrée, lobster asopao (from $40 per pound), is serious business, however: Presented in a cast-iron pot, this refined take on the homey Puerto Rican seafood stew is made with fresh spiny or Maine lobsters grabbed right before your eyes from a vast illuminated tank.
Get transported to the Roaring ‘20s at 1919, the Art Deco-inspired new restaurant at the soon-to-open Condado Vanderbilt Hotel, located in a storied Spanish Revival building. Chef Juan José Cuevas returned to his native Puerto Rico in 2012 after training with the likes of Alain Ducasse at the Essex House and Dan Barber at Blue Hill. The menu here reflects Cuevas’s eye toward sustainable cuisine: Order the delectably moist olive-oil-poached salmon with a minestrone of locally sourced fresh herbs and beans ($33), followed by a house-made ice cream or sorbet ($12), in flavors like tomato-strawberry and sesame seed. Stay for a drink at the adjacent cocktail lounge, Marabar, and sip a Bacardi Reserva Limitada ($19), a limited-edition rum mellowed in charred-oak casks, while admiring the azure Atlantic waves outside.
3. What to Do
Explore the colorful, working-class neighborhood of Santurce, which has recently evolved into an arts and design district. In 2010, a scrappy area gallery, C787studios, began hosting an annual cultural festival called Santurce es Ley, adding a shot of energy to San Juan’s alternative arts scene. Look out for the strikingly complex graffiti that covers many of the sidewalls on Cerra and Hoare Streets. Then head to Roberto Paradise, a two-year-old gallery exhibiting avant-garde contemporary artists like José Lerma and Tyson Reeder in a wood-walled residence from the early 1900s. A few blocks away, gallerist Agustina Ferreyra shows mixed-media and conceptual works by emerging artists from Puerto Rico and beyond.
Hear up-and-coming indie musicians at La Respuesta, a warehouse-like venue with a formidable roster of performances by irreverent, underground local acts like Campo Formio, a powerful post-punk trio, and the singer-songwriter Mima, who plays a mix of folk and Afrobeat. On weekends, catch internationally known music makers like Richard Dorfmeister (of Kruder & Dorfmeister) or Brooklyn Shanti (dubbed the “Indian Bambaataa”) at La Factoria in Old San Juan. Opened just a year ago, this specialty-cocktails bar could have been transplanted right from South Williamsburg, with tattered walls, vintage floor tiles, string globe lights, and a staff of knowledgeable mixologists crafting quaffs like the spiced Old-Fashioned ($10).
Check the calendar at Beta-Local, a nonprofit in Old San Juan that has become a harbor for progressive artistic thought and expression. The space hosts frequent film screenings, exhibits, and workshops about topics ranging from the use of technology to create art to the tenets of raw foodism, offered on the ground level of a grand residence from the early 1800s. The 9,000-square-foot building was fully renovated by Beta-Local founder Michy Marxuach, a respected curator who lives with her family on the top floors. Ask if you’re there in time for one of her donation-based Friday dinners, which support visiting artists like Venezuelan photographer Angela Bonadies; recent meals have included rustic classics, like chicken with spicy mole sauce served with jasmine rice.
4. Insider’s Tip
Pork-loving travelers repair to the mountainside town of Guavate, 30 miles south of San Juan, to work their way through the Ruta del Lechón (hog highway), a steep country road filled with lechoneras, or open-air cafeterias selling juicy spit-roasted pork with the usual trimmings: rice and beans, fried plantains, piña coladas. But if you’re not up for the drive, you’ll find the same traditional flavors and folksy atmosphere right in the city at Santurce BBQ (115 Degetau Street. 787/727-0341), a modest eatery next to a bare-bones cement patio where whole pigs are roasted every weekend for lunch.
5. Oddball Day
After delving into San Juan’s urban side, get moving and explore the seaside outdoors. Sweat out the weekend’s indulgences with a vigorous morning class at Ashtanga Yoga in residential Ocean Park. David Kyle, the remarkably flexible Louisianan who opened this bright, clean-lined studio five years ago, teaches an intense style of vinyasa aptly called The Rocket. Afterward, walk a block to Kasalta for a well-earned breakfast of a mallorca ($1.75), a fluffy sweet bun the size of a small birthday cake, which pairs perfectly with café con leche ($1.50). Drive ten minutes to the beach in Isla Verde, where Wow! Surfing School offers lessons to both neophytes and more seasoned surfers in temperate, moderately rippled waters. After you’ve dried off, roll down your car windows and make the 30-minute road trip to the eastern coast of the island, stopping for a hearty lunchtime snack in Piñones, a somewhat rickety but charismatic beachside community filled with chiringuitos, shacks peddling fritters like beef alcapurrias (from $1.50), made with taro root and green banana batter. From there, take Interstate PR3 to reach the town of Fajardo, home to one of the island’s three bioluminescent bays, whose waters are filled with microscopic plankton that glow when touched. In spite of its proximity to San Juan, Fajardo’s Laguna Grande nature reserve feels worlds away and is kept reasonably uncrowded. Tour operators like Las Tortugas Adventures guide you on a nighttime kayak trip to the lagoon, leaving from a beach and passing through an enchanting stream ensconced in overgrown mangroves. You’ll finish just in time for dinner, so speed up the drive back by taking Route PR66, which should get you to Old San Juan in less than an hour. End the night with a board of brie, havarti, and manchego cheeses ($18), charcuterie ($22), and a bottle of crisp Dominio de la Vega cava ($28) at Al Fresco, a brick-walled wine-and-tapas bar on the top level of a three-story Colonial home. The terrace, open until 11 p.m., is an ideal vantage point from which to admire the pastel facades of the cobblestoned historic district.
Avenida de las Artes provides a comprehensive guide to the Santurce arts district, with a visual history of the neighborhood, suggested street-art routes, and schedules for performance venues.
Sal.pr, published by Puerto Rico’s main newspaper, El Nuevo Día, is a comprehensive restaurant guide with user reviews.
To learn more about the island’s unique bioluminescent bays, check out biobaypuertorico.com, which includes a useful moon calendar (nights with a bright moon should be avoided).
San Juan’s small but vibrant alternative art scene is blogged about at length at Puerto Rico Indie.
Puerto Rico Day Trips will not be winning a web design award any time soon, but it provides useful information about everything from hidden beaches to street festivals