San Juan is a city of contrasts: 500-year-old brick casas sit next to gleaming glass-and-steel hotels. Caribe Indian, Spanish and African cultures compete and combine in every conceivable way. Busy highways divide affluent and struggling neighborhoods. An U.S. commonwealth, its residents are Americans, but more proudly Puerto Rican.

Nowhere are these contrasts more apparent than on the tables of the city’s homes, restaurants and hotels. The cuisine is a tribute to the island’s multi-cultural heritage, colonial rulers and global commercialism.


Eat Like a Tourist

An UNESCO World Heritage site, Old San Juan is a 500-year-old city, ringed by stone walls and guarded by picturesque forts. Millions of visitors descend on the cobblestone streets, many arriving on cruise ships, eager to take a trip back in time to a colorful period in history.

Tourism is a crucial industry for the cash-strapped island teetering on bankruptcy and there are plenty of businesses content to take some of that money. It’s not enough to walk the streets or hop on a bus to experience the real history and culture of San Juan.

Flavors of San Juan is one of a handful of companies that offer three- to four-hour culinary walking tours of the old city for $69 – 79 per person at Our tour, on a muggy June afternoon, was led by Pam, a perky 20-something with a degree in physical therapy, an interest in history and a love of food. We met at the art deco Banco Popular tower near the cruise terminal and learned that our tour would include 10 tastes and three drinks.

We headed along the base of the old city walls to Princesa restaurant, the city’s only completely outdoor eatery. Operated by Rums of Puerto Rico, the island’s rum marketing organization, the arborial restaurant featuring dishes inspired by an 1859 cookbook. After a rum tasting led by master bartender Emedin, we settled down for a croquette made with chicken, Iberico ham and “20 secret ingredients” and fried eggplant dusted with brown sugar and cinnamon.

Moving inside the 20-foot-thick, “two-ply” city walls, we wound our way up the hill for panoramic views of the bay and stories of San Juan’s founding. After enjoying a refreshing passionfruit popsicle from Señor Paleta, a local craze, we learned about the competing histories of the piña colada, reportedly invented by two bartenders named Ramon, one at a local restaurant and the other at the famed Caribe Hilton on Condado Beach.

Along the way, Pam pointed out local landmarks, including the six-foot wide apartment that once held a place in the “Guinness Book of World Records,” the famed Parque las Palomas or “Pigeon Park” and La Fortaleza, the Governor’s mansion. We also passed one of Old San Juan’s newer gay bars, Polo Norte, which advertised drag performances and is reportedly popular with the bear crowd. A cold cocktail would have helped beat the heat, but this club doesn’t open until the sun goes down.

Our tour then took us to the 16th-century Cathedral de San Juan Bautista where Spanish explorer Ponce de Leon’s remains are buried and ringed by streets with distinctive blue cobblestones that served as ballast in the ships. There we mashed fried green plaintains into mofongo, the Puerto Rican national dish, and sipped sangria at Rosa de Triana, a Spanish restaurant housed in the vaulted jail cells in the basement of the first city hall.

Pam led us through the modern town square, Plaza Da Armas, named for the armory, to our last stop, Casa Cortés ChocoBar. There we sipped the slightly bitter Puerto Rican hot chocolate and even dipped cheese, a local custom. It seemed counterintuitive, but then again, Americans are known to melt cheddar cheese on a warm slice of apple pie.

A multi-generation, family-owned business, Cortés manufactured popular chocolate bars that included miniature comic books inside the wrapper. Generations of Puerto Ricans learned to read and write with the help of these books. The family’s educational mission continues with a non-profit art museum located about the restaurant, that serves up chocolate in every sweet and savory dish.

As Pam departed, many of us headed back to our favorite spots to take advantage of the discounts for tour participants, all a little wiser about Old San Juan’s history, culture and food.


Eat Like a Local

San Juan’s professional and hipster crowds congregate nightly at Lote 23, Calle San Sebastian #148, an outdoor food court nestled between towering office buildings in the Santurce business district. The long and narrow space, decorated with colorful murals by street artists and pulsing with music by a young DJ, is divided into four terraces featuring 16 different culinary concepts and even a rotational kiosk, all staffed by rising local chefs.

You’ll find everything from perfectly fried chicken sandwiches by chef Pierre-Philippe Saussy’s Hen House to steamed Korean bao buns with a Puerto Rican twist at Paxx Caraballo’s El Baoricua. Don’t skip the tomato and onion confit “abu relish,” named after Paxx’s abuela (grandmother), and the vegan kimchi. At Dorotea’s, chef Raúl Correa uses a custom-made wood-burning oven to bake crispy, thin-crust Neapolitan pizzas. Dorotea’s is reportedly named after Correa’s pet chicken from childhood. How’s that for a colorful island story? 

At El Joint Burger, chef Franco Busó García grills creative burgers with a myriad of pickled veggies, gourmet cheeses and delicious sides. And in the next kiosk, Bayard, salty French fries are served up in paper cones and dipped in both sweet and savory tomato sauces and mayonnaises. Other stands offer traditional Puerto Rican pork dishes and tangy, fresh Peruvian ceviche.

Wash it all down with a local beer, or better yet, a potent slushy cocktail from La Factoria, a creative cocktail bar housed in a converted silver Airstream trailer. Finish the meal with a popsicle from Señor Paleta, a local chain that has locals addicted to fruity and creamy frozen treats. 

Most dishes and drinks at Lote 23 kiosks were under $9, with some even more affordable. The best way to enjoy the experience is with friends. Order a variety of dishes and then share at the picnic tables while passing the night playing giant versions of checkers, jenga and other games.

For a more authentic Puerto Rican experience, enjoy a quick meal at España, AO-23 Centro Comercial Villamar, Marginal Ave. Baldorioty de Castro in Carolina near Isla Verde. You can’t miss the sign from the highway. The Spanish cafeteria, a family operation founded in 1972, feeds a steady stream of locals all day long. Breakfast might include fried or scrambled eggs, Mallorcan cheeses and ham and toasted baguette slices. For lunch and dinner, step up to the sandwich counter and order one of their signature Cuban or “Media Noche” sandwiches or a toasted sandwich filled with nearly a pound of ham, Bonito Español or beef. Don’t forget a side of Spanish potato salad.

Dinner might start with a crispy chorizo or ham croquette, followed by the saffron-tinged, seafood-laden paella or, for a heartier meal, rice with pigeon peas or red beans. Styled after European markets, a meal might involve stops at several different counters and the dessert case should not be skipped. The guava tarts and Mallorcas are to die for.

If you really want to eat like a local, take a trip outside the city on the “Pork Highway.” The Pork Highway, or La Ruta del Lechón, is a roughly three-mile stretch of Route 184 in a central area of the island called Guavate, about 45 minutes south of San Juan. This winding road is lined with more than a dozen casual roadside restaurants, known as lechoneras, specializing in slow-roasted whole pig, lechón. Each restaurant uses a unique (and usually secret) combination of spices to season the pig, which is then roasted over an open fire for six to eight hours.

A weekend tradition, a trip along the Pork Highway is also a cultural experience as the locals turn out to enjoy food, music and dancing. The Pork Highway is hardly undiscovered—it’s been featured on television by Anthony Bourdain and Andrew Zimmern—but still retains plenty of charm. Several local tour companies offer three- to four-hour bus trips starting at around $45 per person.


Eat (and Drink) Like a Gourmet

Executive chef Victor Woods of the Courtyard by Marriott Isla Verde Beach Resort got his start in the kitchen, cooking traditional Puerto Rican dishes alongside his mother. After completing his culinary training, he joined the hotel a decade ago, working his way through the ranks to the top position in the kitchen.

“It’s not work to me, it’s more like a hobby,” the handsome young chef said of his job with a humble grin. “I enjoy it every day.”

The menus of the Courtyard’s five restaurants and bars all pay homage to the heritage instilled during hours in the kitchen with his mother. But, he’s not afraid to experiment with the fresh seafood, fruit and local staples, either, transforming common ingredients into sophisticated gastronomic delights.

The tapas menu at his beachfront restaurant, Sirena, features crunchy fried lobster bites coated with smoky chicharrones (pork rinds), deep red ahí tuna tartare with a tangy tamarind glaze served on a crispy seaweed risotto cake and crispy Cuban sandwich spring rolls loaded with salty ham, Dijon mustard and creamy cheese to be dipped in green mayo ketchup.

For dinner, try the pan seared Atlantic halibut served with risotto laced with longaniza Spanish sausage and finished with a lemon saffron broth or his signature Sirena Strip and Shore, a perfectly cook tenderloin accompanied by large fried shrimp coated in a golden codfish batter. Decadent is the only word to describe the dish.

At the LaConcha Renaissance San Juan Resort, mixologist Timmy Ortega is a superstar. He serves a worldy clientele at the Condado Beach resort, located in the heart of San Juan’s upscale shopping and hospitality district, and he always has to be on his game. A protege of famed Spanish restaurateur Jose Andres, he was instilled with an insane attention to detail and quality ingredients.

“He taught me what real flavors are about,” said Ortega of his mentor Andres. “We have to tell the guests a story with every taste.”

A simple piña colada won’t do for the guests at his bar. He might add a spritz of aromatic chocolate bitters to a martini, a sprig of fresh herbs to a mojito or whip up a salt-infused foam on top of a margarita. Smoke, foggy dry ice? He’s prepared. His inventive creations have been the ticket to prestigious bartending competitions around the world.

He laments the latest trend in Puerto Rico, frozen cocktail machines. Most churn out sugary slush. If one of his customers desires a frozen cocktail, Ortega is more likely to pull out a canister of liquid nitrogen and do it himself.



Courtyard by Marriott Isla Verde Beach Resort

7012 Boca de Cangrejos Ave.

Carolina 00979

The Courtyard by Marriott Isla Verde Beach Resort is like no other Courtyard property you’ve ever stayed—guaranteed. While Courtyard is one of Marriott’s budget-conscious, “sensible” business and family-travel brands, that’s definitely where the comparisons end. This hotel’s recently-remodeled 260 rooms are located on the pristine, Blue Flag-certified Isla Verde beach, voted best urban beach on the island. Swing on a restful hammock, sip cocktails at the swim-up pool bar or take in a surfing lesson at the nearby Waterworld Surfing School. The jewel of the property is Sirena, the hotel’s beachfront fine dining restaurant, featuring a menu of creative contemporary tapas and fresh seafood. The only reminder of civilization is the occasional sound of jets taking off from nearby Luis Muñoz Marín International Airport. After the spectacular sunset on Isla Verde Beach, the night is only beginning in Picante, the lobby bar that features spicy salsa music, and the adjacent Casino Del Sol. Courtyard by Marriott Isla Verde Beach Resort is a 10-minute cab or Uber ride from LGBT nightlife in Condado and Santurce, and 20 minutes from Old San Juan.


La Concha Renaissance San Juan Resort

1077 Ashford Ave. 

Condado, San Juan 00907

Located in Condado, San Juan’s bustling shopping and nightlife district and a short walk (or shorter ride) from many of the most popular gay bars and nightclubs, La Concha Renaissance San Juan Resort is a tribute to mid-century design with its historic, floating sea shell restaurant, Perla, formerly the resort’s nightclub and today, one of the island’s highest rated. After a $220 million renovation, the resort features 485 comfortable, contemporary guest rooms, most with sweeping ocean views; a stunning adults-only infinity pool that overlooks one of the most popular corners of Condado Beach; and a fully-appointed spa, business center and event spaces. After the sun goes down, the action moves to the hotel’s expansive lobby, managed by J.C. Pappas. Most nights, DJs spin Latin rhythms and dance beats into the early hours of the evening and the mojitos and designer cocktails flow. Pappas, along with his equally handsome husband, was featured in the island’s first gay marriage ads and also leads a staff committee that plans activities for the hotel’s LGBT guests and community. The hotel hosts 15 to 20 same sex weddings each year.



Mofongo is Puerto Rico’s national dish, a staple of any meal. The fried and then mashed green plantains, flavored by smoky pork rinds and garlic, are the ultimate comfort food, hearty and filling, and often crowned with tangy chicken, beef or seafood. Any local will proudly tell you that his (or her) mother or grandmother make the best mofongo they’ve ever tasted. Our friends at Taste of San Juan shared this recipe for mofongo and creole chicken so you can sample this Puerto Rican classic for yourself.



Serves: 2-4 people

Prep time: 10 minutes

Cooking time: 30 minutes



4 firm green plantains


1/2 lb. fried pork rinds

1/2 cup chicken stock

Salt and pepper to taste

2 garlic cloves, peeled and crushed

Pilon and mortar (Puerto Rican mortar and pestle)

Vegetable oil for frying



  1. Peel plantains and cut into several 1 inch wheels.
  2. Place plantains in water, with 1/2 cup chicken stock and pinch of salt for 5 minutes.
  3. Create a paste with the garlic cloves and a teaspoon of salt by mashing them together in the pilon.
  4. Strain partially boiled plantains and place in deep fryer until golden brown (for about 5 minutes).
  5. Place plantains in the pilon and begin mashing them together with garlic and salt until you can no longer see the individually cut plantains (but not too mashed like mashed potatoes; never use a food processor), adding a little bit of the garlic mixture at a time.
  6. You will have to work a few slices at a time in order to get everything mashed. The mofongo is complete once everything is mixed up and there is even distribution of seasoning.
  7. Once you’re done, push all the sides down at an equal level, leaving room for the chicken to sit in the mofongo.


Chicken in Criollo Sauce

Serves: 2-4 people

Prep time: 15 minutes

Cooking time: 30 minutes



4 chicken breasts, skinless and boneless

1 onion

1 yellow pepper

1 green pepper

8 oz. tomato sauce

4. oz tomato paste

2 garlic cloves

1 pinch oregano

2 tsp. salt

1 tsp. pepper

1 pinch cilantro



  1. In a large pan, sear the chicken breasts until they are done.
  2. Take chicken out of pan and rest on a plate.
  3. In a large saucepan, heat a small amount of the vegetable oil, add vegetables to sweat for a few minutes.
  4. Add the cooked veggies, tomato sauce and tomato paste, spices and chicken and simmer for 20 minutes, stirring occasionally.
  5. Once both dishes are made, place the chicken into the mofongo and enjoy!