Food at  1919 at the Vanderbilt Condado, Puerto Rico, Caribbean

1919 at the Vanderbilt Condado

Mingle with the locals at the bar of this historic hotel. The Vanderbilt’s flagship restaurant, 1919, occupies what was the setting for society weddings, balls and major events for generations of San Juan’s elite. After back-to-back Michelin-starred culinary projects that also earned him the title Chef de l’Avenir (Chef of the Future) by the International Academy of Gastronomy, Juan Jose Cuevas returned to Puerto Rico to be executive chef at 1919.

Dishes are avant-garde adaptations of traditional preparations (Puerto Rican phrases are sometimes in quotes to indicate variation) or global cuisine mainstays like Tuna Sashimi. Menu descriptions are minimal but flavors are big; choose pre-fixe or à la carte for both lunch and dinner. Reservations are highly recommended.

Food at Bili, Vieques, Caribbean

Bili

For casual local cuisine, Bili offers delicious island food at a reasonable price. Eva Bolivar, former private chef to a Puerto Rican governor prepares the authentic food in this Mediterranean-style tapas restaurant.

Chez Shack

Famous for its weekly barbeque night with a steel band, Chez Shack restaurant is located off the beaten bath in Vieques’ tropical hills. Owner Duffy (the original proprietor of Duffy’s in Esperanza) serves a variety of chicken, beef, and seafood, but the menu changes often. Reservations are highly recommended.

Duffy’s

The island’s most popular hangout, Duffy’s is regularly full of a crowd posted up by the bar chatting with owner Michael Duffy. Serving standard finger foods, burgers, wraps, and fries, as well as specials like conch fritters and fish tacos; this waterfront restaurant’s open-air dining room is the perfect spot for lunch.

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Food at El Blok Bar and Restaurant, Vieques, Caribbean

El Blok Bar and Restaurant

Located on the second floor of El Blok hotel, this eponymous restaurant serves refined Puerto Rican cuisine. Helmed by San Juan native Jose Enrique (named Food & Wine’s Best New Chef in 2013), El Blok serves rustic fare that emphasizes grilled dishes and locally sourced vegetables. The open terrace is the perfect spot to watch the sun set.

El Quenepo

Owners Scott and Kate Cole serve elevated Caribbean cuisine at this waterfront restaurant in Esperanza. The menu focuses on local herbs and fruits as well as seafood dishes highlighting the catch of the day. More casual high-bar tables are available for walk-ins, but reservations are highly recommended here.

Outdoor Lounge at Encanto Bar, Puerto Rico, Caribbean

Encanto Bar

Located at the end of the West Beach buildings at Ritz-Carlton Dorado Beach, Encanto is an open-air experience offering freshly grilled fare for lunch and Asian-influenced cuisine at dinner. For a light lunch, order the fish tacos and have them delivered directly to your beach chair.

Factoría La Sanse

The burnt-orange-colored building on the corner of Calle San Sebastían and Calle San José seems like the last place one might stumble upon a ‘cocteleria artesanal’ (artisanal cocktailery). But follow the advice of a local and, “keep walking through the doors” of the unmarked building, and eventually you will enter the dark speakeasy-style mixology lounge. Menu offerings are tasty and interesting, but sometimes it’s more fun to tell the bartender your preferred flavor profile and have him make you a customized cocktail.

Food at Hotel el Convento,  Puerto Rico, Caribbean

Hotel el Convento

The landmark building housing Hotel El Convento has only seen two renovations in the 356 years since it was built as the first Carmelite convent in America. Entering the glamorous, old-world lobby feels like taking a step back in time; wall tapestries tell the stories of Spanish conquistadors responsible for the building’s existence and a grand piano sets a timeless tone. While the hotel rooms feel outdated and claustrophobic, sipping cocktails at the bar or enjoying a fresh, simple meal in the cluster of wrought-iron furniture at Patio del Nispero, one of three in-house eateries, is divine.

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Food at Jose Enrique, Puerto Rico, Caribbean

Jose Enrique

Named for the first Puerto Rican nominee for the James Beard Award’s “Best Chef South” category in 2013, this restaurant also benefits from the local, seasonal offerings at the San Juan farmer’s market, La Placita. The menu is written on a whiteboard, so when a supplier delivers a new ingredient in the middle of service or hungry diners wipe out an item early in the evening, adjustments can be made easily. Reservations are not accepted, so after a walking tour of Old San Juan, put your name on the list on the early side and enjoy a drink at the bar until your table is ready.

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Interiors at Kasalta, Puerto Rico, Caribbean

Kasalta

Kasalta bakery and restaurant is a San Juan institution known for its perfectly toasted sausage sandwiches with just-greasy-enough fries and “chicharrones de pollo” (Puerto Rican fried chicken). Locals stand by the consistently delightful sweets baked on the premises. The light, spongy cake swirled with apricot compote and topped with whipped cream and chocolate make venturing to the edge of Condado, (technically Ocean Park) worth the trip.

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La Ana de Cofresi

The mural adorning the walls of La Ana de Cofresi tells the story of Roberto Cofresi, a Puerto Rican pirate known for his altruism and charity, and his ship ‘La Ana.’ Fishing nets and buoys separate the dining area from the kitchen and El Bohio beach bar is set in the sand. The bar and restaurant along with the adjacent hotel have been owned by a local family since their inception in the 1960s, and remain local favorites. The Bohio’s “Pirate Special” cocktail, which consists of several different types of alcohol and is served in a coconut with a straw in it, claims international fame. Even if the campy décor and local infamy aren’t your thing, know that their mofongo, a traditional Puerto Rican dish prepared with fried then mashed plantains and meat, is one of the best on the island. The place may be tricky to find, so get specific directions from your hotel.

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Marmalade

Chef-owner Peter Schintler’s several-page à la carte and tasting menus boast French culinary staples like fois gras, but his are paired with warm blackberry sauce and sausage confit. Every dish has a carefully chosen wine pairing suggestion and the ingredients' origins are clearly stated. After grazing on mostly fried Puerto Rican fare for a few days, the full page of vegetarian mains is welcome. Many dishes star a single, unique and delightful flavor or color, such as a recent dish that highlighted candy stripe beets, raspberries, pistachios, mint and verbena oil. (The menu also describes the restaurant's involvement with the Natural Resources Defense Council and the Monterey Bay Aquarium and its involvement in the protection of over-fished and endangered species.)

Editors' Picks
Interiors at Positivo Sand Bar,  Puerto Rico, Caribbean

Positivo Sand Bar

Open daily from 11am through dinner, Positivo has tables sitting in the sand and offers a casual dining atmosphere, serving a selection of bites like skewers and ceviche. The bar area is fun and lively at night, and there are three large pods that couples can rent while they sip drinks overlooking the bar and pool area.

Interiors at Santaella, Puerto Rico, Caribbean

Santaella

It is no coincidence that chef José Santaella’s rustic-chic restaurant is less than a block from La Placita, San Juan’s farmer’s market. The dining room tables overlook an interior greenhouse-type garden and a playful flora-themed mural decorates the bar area. Here, fresh, local and whole are the name of the game, and sharing is too.

With a few exceptions, the dishes on the menu are arranged from smallest to largest, encouraging diners to choose based on the highlighted flavors and ingredients that appeal to them, instead of following formulaic courses in succession. This style of service not only makes the appearance and preparation of each dish a potential surprise, but also changes the function of a meal, which is no longer an obligatory affair, but a communal experience.

Editors' Picks

Tin Box

Tin Box serves outstanding cocktails using fresh fruits and herbs from an onsite garden. Specialty drinks include a watermelon margarita and a virgin Bloody Mary, made with 18 different vegetables and herbs. Tin Box also boasts a raw bar oyster bar.

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