Ultimate Food Weekend: San Juan, Puerto Rico

By Kathleen Squires  |  January 6, 2014

Today, January 6, happens to be Three Kings Day, so if you find yourself on the Island of Enchantment, get ready for parades and feasting to celebrate the culmination of the Christmas season. The festivities don't end today: Old San Juan continues the party with the Fiestas de la Calle San Sebastian, January 16-19, an annual blowout street party full of good food, music and entertainment. But San Juan doesn’t need an occasion to be a great destination for good eating and drinking. Here is our guide to everything delicioso in San Juan.

  • The City’s Signatures

    Frituras are deep-fried street snacks that are a huge part of San Juan's beach culture, despite what they might do to the beach body. Sand-fringed Piñones is the prime hunting ground for fritters, with a line of kiosks along Highway 187 that proffer such treats as bacalaitos, or golden-brown codfish discs; alcapurrias, or oblong fritters stuffed with meat or fish; or pastelillos, turnover pockets bursting with meat, cheese, root vegetable or fish fillings. Some of our favorites include Los 3 Pinos; El Regreso; La Comay; El Boricua and Donde Olga.

    Other great snacking stops include TresBe (1805 Calle Loiza), a cafe fashioned from a shipping container, with terrific fish tacos and lobster empanadas. El Churry is a classic food truck that made its name for its chicken and skirt-steak sandwiches, preferred late-night post-drinking bites since the brand's founding in 1998.

    Reel in a classic chillo frito, a fresh, deep-fried whole snapper at La Cueva del Mar (1904 Calle Loiza). Their thick, rib-sticking pigeon pea soup (sopa de gandules) is a special to watch out for too.

    For classic Puerto Rican specialties in a lovely hacienda setting, it’s hard to beat Casita Miramar (605 Miramar Ave). A glance at the menu lends a primer on the island’s essential eats. All of the staples are here, from pasteles (green banana or root-vegetable tamales) to mofongo (mashed green plantains), asapao de pollo (chicken stew) and exemplary tostones (fried green plantains).

  • Credit: Hernan F. Rodriquez

    Top Toques

    Though he has been wowing diners in San Juan for almost seven years, José Enrique Montes caught a lot of attention only last year for being the first-ever Puerto Rican chef to nab a James Beard Award nomination for his terrific restaurant, Jose Enrique, as well as being named a Food & Wine Best New Chef for 2013. Here, authentic local flavors meet outstanding technique in humble, homey surroundings. The menu changes daily, but hope for his carne guisada (beef stew with root vegetables), dorado fish with chickpea stew and alcapurrias (fritters) stuffed with amazingly fresh crab.

    Locals were thrilled when acclaimed caterer José Santaella decided to open his own restaurant in 2011. After all, he’s worked with some of the world’s best chefs, including Ferran Adria, Gary Danko and Eric Ripert. Within the tropical-urban ambiance of Santaella, diners can expect elevated treatment of local dishes, such as traditional roasted pork with rice, pigeon peas and plantain escabeche to internationally influenced creations such as popcorn chicken in curry and agave.

    Juan José Cuevas brings his commitment to locality and sustainability from New York City’s Blue Hill, where he served as executive chef for four years. At 1919, the chef has an especially golden touch with fish dishes, such as a signature cod with local corn, young onions, shellfish and chive.

    The beauty is in the details at Marmalade, from chef Peter Schintler’s slowly melting chile-flavored ice cube and the basil infusion in his tostones to his obsession with using local product. It is one of the only restaurants in San Juan that features a vegetarian tasting menu; fish fans and land lubbers should not miss out on queen snapper poached in coconut water or the heritage Berkshire pork cheeks with barbecued black-bean purée.

    Former Top Chef Master contestant Wilo Benet has been serving modern Puerto Rican food for over 20 years at his legendary Pikayo. His small plates are particularly playful: pegao, the crispy rice at the bottom of the pot, serves as a crunchy bed for silken tuna, and lumachina pasta makes the perfect vehicle for creamy, bisque-inspired sauce with jueyes, a local land crab. 

    The dishes at Laurel within the Museo de Arte Puerto Rico are as artful as the surroundings. Chef Mario Pagan, known for appearing on The Next Iron Chef in Season 3, adds luxury to common ingredients: an ordinary sea bass, for example, is paired with foie gras and port reduction.

  • Markets

    Discover root vegetables and tropical fruits you never knew existed at La Plaza del Mercado, aka “Placita Santurce,” which dates to 1910 and is open daily. In addition to browsing the island’s bounty, you can grab a fresh-made batida (fruit shake); dig into a lunch of fresh fish at the humble, reliable El Tasca del Pescador; grab a cold beer or margarita at the brand-new Mexican cafe Pancho Villa Casa de Tequilas; or pop into a botanica to buy powerful, magic herbs.

    The Mercado Agricola Natural in Old San Juan is the island’s first organic market, started in 2010. Every Saturday from 8 AM-1 PM, locals come not only to search the finest of island produce, but also to enjoy prepared foods such as vegetarian empanadas, cooking demonstrations and socializing with the engaging three dozen vendors.

  • Breakfast/Brunch

    Sanjuaneros aren’t big brunchers, but they do enjoy a good breakfast. Charming St. Germain in Old San Juan offers a Puerto Rican spin on the mimosa - champagne with guava juice - alongside classic brunch dishes such as omelets and eggs Benedict. Pop over to Caféteria Mallorca (300 Calle San Francisco) and belly up to the counter to try a real Puerto Rican delicacy for breakfast: the mallorca sandwich, a sweet bread sprinkled in powdered sugar and stuffed with cheese, ham, egg or all of the above. Nearby on scenic Plaza Colon, Caficultura is a lovely spot, whether indoors or outdoors, to grab a morning meal with a great cup of coffee.

  • Sweets

    Piragua are shaved ice cones flavored with syrup. The refreshing flavorings smack of the tropics - from coconut to passion fruit. Look for piragueros selling them from their pushcarts around Old San Juan - a good bet is you’ll come across one by El Morro Fort or around Plaza Colon. Another frozen treat is the limber, a frozen, sorbetlike dish that also comes in tropical flavors. To try one, go to the four-decade-old, family-run Caleta de las Monjas 9 in Old San Juan (look for a hand-lettered sign in front). Kasalta in Ocean Park is also a popular stop for its shelves of pastries, especially the sweet cheese crullers known as quesitos.

  • Credit: Alden Gewirtz


    Heaven for java junkies, a rash of quality coffeehouses serving locally grown and roasted brews are sprouting up around the city. Right from the plantation to your cup, Café Finca Cialitos “Expresso Art” is owned by a master cupper and coffee farmer. Coffee growing has also been in the family blood of the owner of Café Cuatro Sombras since 1846. Workshops and cuppings are given in the shop regularly. Freshest-out-of-the-pot is Hacienda Isabel (201 Calle Sol), which just opened in Old San Juan at the end of 2013, while Café Poetico (203 Calle Cruz) features poetry performances along with its local roasts.

  • Cocktails

    If there was ever a reason to start a personal “rum diary,” it would be a trip to San Juan. A trip to Casa Bacardi gives a good overview of the process from sugarcane to bottle. Free samples are included, and it’s a nice boat ride across the harbor from Old San Juan. Local favorite Don Q has a tasting room in Old San Juan near the cruise-ship port, with a similar historical overview. Barrachina, meanwhile, claims that it is the “birthplace of the original piña colada” - the first one was served here in 1963. For an example of the burgeoning craft-cocktail movement, La Factoria (148 Calle San Sebastian) is the destination for mixology enthusiasts. Los 2 Cuernitos, a restaurant that features the “cooking of a Puerto Rican Grandmother,” also serves up rum-based chichaito shots in 50 flavors.

  • Wine

    The sangria at Chef Roberto Trevino’s Bar Gitano is top-notch, and the Spanish wine selection next door at El Barril complements the lively music and dance scene. Vino (148 Calle San Sebastian), a speakeasy wine bar tucked behind the cocktail bar La Factoria, is a well-kept secret with creative tapas.

  • Beer

    Nine-year-old microbrewery Old Harbor took home a World Beer Cup award in 2010. Its beer selection is widely available throughout San Juan and at their own Old San Juan pub. You’ll find about 50 beers on tap and more than 100 by the bottle at La Taberna Lupulo (151 Calle San Sebastian). For a cheap, classic Medalla, nicknamed the “Borinquen Bud,” a stop at the classic dive El Batey is a must. Think CBGB’s, without the live music but with a killer jukebox and pool table instead. Biercade is a fun spot to sip suds and play retro arcade games.

  • Where to Stay

    O:live Boutique Hotel is a small, cool, Mediterranean-styled villa with a popular restaurant and an exclusive members club, complete with plunge pool and views, on the roof.

    El Convento is a historic, transporting ex convent, conveniently located in the thick of Old San Juan.

    The Condado Plaza Hilton has all of the resort amenities on-site, right smack on the beach, and steps away from fashionable Condado shops and restaurants.