An Insider’s Guide to Puerto Rico: Where to Eat, Stay, and Play

“Puerto Rico, my heart’s devotion…” As a child, I was entranced by Rita Moreno singing these words as Anita in the Academy Award-winning film, West Side Story. Of course, Anita goes on to diss her homeland and professes her love to another—the isle of Manhattan—but when I finally got the chance to visit Puerto Rico for myself, I realized how wrong she was. I’m with Bernardo on this: “I like the city of San Juan!”

My first trip to Puerto Rico was three years after Hurricane Maria. Driving through the countryside, there were still remnants of what was considered the worst natural disaster in the island’s history. I saw blue tarps fastened to roofs and bare trees steadily growing back to their former emerald glory. Visiting my family in Cayey, I heard stories of how loud the winds were. How walking out the next morning to see the damage, it appeared the rainforest had been burned, robbed of all vegetation. No power for five months. Over a game of dominos at my grandfather’s house, and fresh papaya plucked from mi tía Noida and tío Efrain’s backyard, the stories were similar but always ended with a faint smile and a “things could’ve been a lot worse.”

Puerto Rico has since regained its old-world charm and contemporary flair. The island continues to thrive, leading both the U.S. mainland and the Caribbean region in tourism metrics according to Brad Dean, the chief executive officer of Discover Puerto Rico. “In terms of visitor demand, lodging yields, tourism tax collections, and leisure hospitality employment, the three best years of Puerto Rico tourism have been 2021, 2022, and 2023,” said Dean.

The island’s versatility offers a choose-your-own-adventure for travelers. It’s a place to find experiences like no other, whether you’re looking to escape the winter blues, or simply to recharge on a solo trip with the latest New York Times bestseller as your only companion.

For personal chef Anjelica Velazquez, flying to the island is a moment in itself. “As the plane lands, the entire cabin erupts in applause as ‘Bienvenido a Puerto Rico’ plays on the speakers,” said Velazquez. “Stepping off the plane, you’re greeted by the unmistakable scent of the sea and the warm embrace of the island's humidity. It feels like my ancestors praising me for making it safely home to the motherland.”

Commercial real estate manager Alex Zyndorf discovered Puerto Rico to be the perfect haven for solo travelers after visiting this past month. “It feels like getting really far away without worrying about where you put your passport,” shared Zyndorf.

It’s also a home away from home for Eli Valentin, co-founder of the creator commerce platform Fourthwall. Born and raised on the island, for Valentin, “introducing others to the real Puerto Rico is one of my favorite things to do. Seeing people learn more about our culture and get exposed to our way of life is just amazing. They learn that this paradise is not far away.” For natives and travelers alike, there are always newfound gems to explore.

Without further ado, here’s the ultimate Puerto Rico playbook with newfound gems from insiders near and far. Now’s the time to book your flight to the beloved crown jewel of the Caribbean—no passport needed.

What to Do

Native artisans sell handmade jewelry and artwork at the Cuartel de Ballajá, housed in military barracks dating back to the 1800s, built to harbor Spanish troops and their families. Several art organizations are also in residence, as well as the Museo de Las Américas occupying the second floor.

Cuartel de Ballajá, Viejo San Juan 00926, Puerto Rico

Explore the Santurce art scene near Old San Juan. There is a maze of urban murals, along with a couple of tucked-away galleries, one of which is Chillums, a glass gallery specializing in “functional art” (aka a selection of hand-blown marijuana pipes).

1606 Ave. Ponce de Leon #L-08, San Juan, 00909, Puerto Rico

El Yunque National Forest is a scenic workout. Hiking in Puerto Rico’s national rainforest is a must, especially for snagging a mythical waterfall #nofilter photo. The gentle croaks of coquís, the native frog of the island, will transport you amid the kaleidoscope of lush vegetation and wildlife.

Driving directions provided on website

Chef Velazquez recommends this sandy destination to get together with family and friends for a lazy day at the beach. Playa El Escambrón is also protected by coral reefs, making it a perfect location for snorkeling. Mere minutes from restaurants and food stands, it’s all too easy to let time slip by as you embrace the island life.

Where to Stay

An art gallery, studio, and boutique hotel rolled into one, The Gallery Inn is full of paintings, bronzed statues, and intriguing ephemera fashioned by artist and lady of the manor, Jan D’Esopo, who discovered the long-lost building in 1961. The on-site Cannon Club has a candlelit concert series with dueling jazz pianos (where you can catch a descendant of the D’Esopo family, Nico, joining in on his violin). Live parrots nibbling on mint leaves grace various perches throughout the space. It’s a total fantasy and the room decor reflects this: heavy wine-colored drapes and gold details, along with lush tropical greenery, hold court in the 27 rooms.

204 Norzagaray Street, Old San Juan, 00901, Puerto Rico

A tranquil stay awaits when choosing LGBTQ+-owned Dreamcatcher as your home base—if only for a few days. Experts in “laidback luxury,” Zyndorf booked her solo trip here, finding every attention to detail beautifully curated, right down to the friendly customer service.

2009 Cll España, San Juan, Puerto Rico 00911

Nestled in a historic building dating back to 1838, Palacio Provincial beckons with breezy French doors that open to Juliet balconies overlooking the candy-colored streets of Old San Juan. A rooftop pool with charming views invites guests to pair a paperback with a chilled mojito, while the open-air courtyard calls you to a candlelit dinner at the Consular Restaurant and Bar.

103 Calle de San Francisco, San Juan, 00901-1538, Puerto Rico

Where to Eat

A professional pan de Mallorca maker, Cafeteria Mallorca, gives off a cozy neighborhood feel. Chances are, if you ask around, you’ll get this recommendation from locals. It is the oldest standing diner on the island and stays open till 3 p.m. purely through word-of-mouth.

300 Calle San Francisco, San Juan, 00901, Puerto Rico

How about a cashew latte to start the day? Café Regina works closely with local producers to offer wake-you-up coffee and beautiful dishes that are almost too pretty to eat. Zyndorf paints the scene: “Cafe Regina feels like comfort, the minimalist decor, the delicious toast, and the indulgent lattes, take it to go and walk it down two blocks for breakfast on the beach.”

1705 Calle La Loiza, San Juan, Puerto Rico 00911

A menagerie of hip food trucks, airstreams, and vendor stalls, Lote 23 is a pitstop that will satisfy a wide range of tastes, whether you’re craving local beers from The Box Lab or savory Caribbean bites from Pa'l Cilantro. There’s also live music and plenty of picnic tables to lure you from the beach.

Av. Ponce de León 1552, Santurce, 00909, Puerto Rico

A shabby and oh-so-chic restaurant, Verde Mesa feels more like a home. I felt I’d completely left reality when I sat down for dinner. Our waitress was a dream and made noteworthy menu recommendations based on the ingredients the chef was partial to that day (i.e. swordfish ceviche and warm naan). The menu changes rapidly to accommodate the freshest ingredients. Owner Loyda Rosa Figueroa pioneered the farm-to-table concept in Puerto Rico, using fresh veggies from her own organic farm or the local farmer’s market in her dishes. Make room for dessert and ask for the purple cloud.

107 Calle Tetuan Esq, C. San José, San Juan, Puerto Rico 00901

After moving to Puerto Rico in 2017, husband-wife team Amelia Dill and Francis Guzmán built their first restaurant, Vianda. Showcasing the flavors of Puerto Rico with farm-to-table flair, the two earned their chops at New York City’s Blue Hill and two-Michelin-star restaurant The Modern. In 2019, Vianda was among the 20 Best New Restaurants in America selected by the James Beard Foundation with Chef Francis Guzmán chosen in 2021, 2022, and 2024 as a semifinalist for outstanding chef. “Fresh, locally sourced in a friendly environment. It would rank the top restaurant on my list,” said Valentin.

1413 Avenida Ponce de León, Santurce, Puerto Rico 00907

With pretty multi-course meals, Marmalade is the sort of luxe spot one goes to celebrate life’s milestones. All the dishes are focused on farm-to-table ingredients. The White Bean Soup sprinkled with black truffles is a local favorite, mentioned to me several times while I was in the city. Suffice to say, it’s on my list for when I return.

317 Calle de la Fortaleza, San Juan, 00901, Puerto Rico

Where to Drink

Wallpapered with doodled-on dollar bills and decorated with mythical horned vejigante masks native to the island (hence the translated name ‘The Three Horns’), Los 3 Cuernos steeped in local longevity. The one-roomed jukebox dive bar specializes in exotically flavored chichaitos, shots made with Anisette liqueur and rum. (Try Nutella or guava.) It’s a perfect first stop for a night out in Old San Juan.

359 Calle San Francisco, San Juan, 00901, Puerto Rico

Looking for an afternoon pick-me-up in the form of an espresso martini? Velazquez offers up Santaella as a way to kickstart your night of salsa dancing. Led by Chef Jose Santaella, you’re in for a night of modern dining with local dishes that put “the vibrant energy of the island’s ‘cocina criolla’” on full display. Valentin agrees: “You get the deliciousness of a fine dining experience with a mix of Puerto Rican fun.”

219 Calle Canals, San Juan, Puerto Rico 00907

The first natural wine bar in Puerto Rico, El Vino Crudo will inspire you through drink and decor. “The butter yellow tile and red lights made me want to run home and decorate my apartment in its color scheme,” said Zyndorf. Located in the center of Old San Juan, the bar strives to bring natural wine to the masses, one biodynamic sip at a time.

320 C. de la Fortaleza, San Juan, Puerto Rico 00901

A champagne and snack bar serving luxurious fizz and caviar-laden bites, Pio Pio’s eclectic menu and interiors are equally Instagram-worthy. If sparkling isn’t your style, there’s a wine list a mile long with knowledgeable staff to help you navigate.

151 Calle de San Francisco, San Juan, 00901, Puerto Rico

With 50 taps and over 150 bottles, La Taberna is a Puerto Rican craft beer bar serving local brews Ocean Lab and FOK, along with mainland and international favorites in a breezy building from the 1700s. The beef sliders and beer fries (more like chips) will snuff out the hunger that comes with a day of trekking through the city.

Opened in the 60s, El Batey Bar gives off a rebel beatnik vibe complete with graffitied walls that invite you to pick up the nearest Sharpie and add to the inky chaos. It’s the perfect setting to chat about the night’s plan under a glowy orange light amplified with jazz tunes playing in the background, and there’s a pool table in the back if you’re feeling restless.

99 Calle del Cristo, San Juan, 00901, Puerto Rico

A Russian doll of a spot, La Factoría reveals a different layer—and bar—on each floor. When you first enter, you’re greeted with a polite speakeasy feel, complete with a puffy couch in the corner and bartenders performing drinks rather than just serving them. I ordered a lavender mule so pretty a couple behind me immediately requested the same. Los Hijos de Borinquen is another cocktail with a cult following. As you go deeper into the boozy labyrinth, the light gets dimmer and the music switches from light jazz to bass-thumping club and then live Spanish beats, where patrons can salsa the night away.

148 Calle San Sebastián, San Juan, 00901, Puerto Rico

Off the Beaten Path

A quick ferry ride away, the island of Vieques sits on the eastern shore of Puerto Rico. You may recognize the name for having glowing reviews as the brightest bioluminescent bay in the world. (There are only five in existence, three of which are in Puerto Rico.) Like something from a dream, wild horses roam the countryside here, and the Vieques National Wildlife Refuge is the largest of its kind in the Caribbean. A recommendation from Valentin, he also recommends checking out Tin Box, a BBQ and Sushi restaurant. “Weird concept, but trust me when I say you will love it—and very laid back, as you would expect from the Vieques Island vibes,” he says. “Definitely try the rumande: a passion fruit lemonade mixed with Puerto Rican rum.”

Within the town of Lajas, you will find la Parguera, a fishing village-esque locale Valentin calls “a true local experience.” He recommends renting a boat for the day or doing one of the many tours available to explore. “If you are into diving, La Parguera is the place to visit. Just a short boat ride away, you will find La Pared, one of the deepest parts of the Caribbean and a great diving spot!” As for where to grab a bite post-dive? “So many options to try, from empanadillas to fresh oysters, but my recommendation has to be El Turrumote. It’s traditional Puerto Rican food with freshly-cut fish. After all, you are in a fishing area! This restaurant is located in La Parguera Yacht Club and is only open from Thursday to Sunday.”

Speaking with mi tía Noida, who lives in the mountains of Cayey, one cannot leave Puerto Rico without visiting Guavate. Pork reigns supreme as you drive down Route 184 to find back-to-back lechoneras—restaurants specializing in slow-roasted pork. Pasteles, morcillas, and many other delicacies are served here. “The lines are long because the food is so good, but they move along quickly,” said Noida. “Our favorite spot is El Rancho Original because the atmosphere is very lively, and it’s built around a beautiful creek that circles the gazebos where people gather to eat, dance, and celebrate any occasion with their loved ones.”

Playa Sucia is an isolated beach protected by the town’s nature reserve with a stunning lighthouse view worth the venture. For Velazquez, she suggests packing a cooler as you take in the beautiful white sands. Note: There’s limited parking, so make sure to get a prime spot to soak up the rays.

Nicknamed “the Pearl of the South,” Ponce is home to the Museo de Arte de Ponce where over 4,500 works of art are on display, from Baroque to Victorian paintings to Puerto Rican and Latin American art. Finish off your cultural tour with a meal at El Negocio de Panchi. Think bright Caribbean flavors with a homey vibe. “All dishes are prepared by chef Panchi himself, and his friendly staff will cater to your needs making you feel right at home,” says Valentin.