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!”
Exploring Puerto Rico’s Charm
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.
Insider Recommendations
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.
What to Do
Cuartel de Ballajá
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.
Location: Cuartel de Ballajá, Viejo San Juan 00926, Puerto Rico
Santurce Art Scene
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).
Location: 1606 Ave. Ponce de Leon #L-08, San Juan, 00909, Puerto Rico
Explore the Rainforest
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.
Playa El Escambrón
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
The Gallery Inn
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.
Location: 204 Norzagaray Street, Old San Juan, 00901, Puerto Rico
Dreamcatcher
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.
Location: 2009 Cll España, San Juan, Puerto Rico 00911
Palacio Provincial
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.
Location: 103 Calle de San Francisco, San Juan, 00901-1538, Puerto Rico
Where to Eat
Cafeteria Mallorca
A professional pan de Mallorca maker, Cafeteria Mallorca, gives off a cozy neighborhood feel. It is the oldest standing diner on the island and stays open till 3 p.m. purely through word-of-mouth.
Location: 300 Calle San Francisco, San Juan, 00901, Puerto Rico
Café Regina
Café Regina works closely with local producers to offer wake-you-up coffee and beautiful dishes that are almost too pretty to eat.
Location: 1705 Calle La Loiza, San Juan, Puerto Rico 00911
Lote 23
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 or savory Caribbean bites.
Location: Av. Ponce de León 1552, Santurce, 00909, Puerto Rico
Where to Drink
Los 3 Cuernos
Wallpapered with doodled-on dollar bills and decorated with mythical horned vejigante masks native to the island, Los 3 Cuernos is steeped in local longevity.
Location: 359 Calle San Francisco, San Juan, 00901, Puerto Rico
Santaella
Looking for an afternoon pick-me-up in the form of an espresso martini? Santaella offers up modern dining with local dishes that put “the vibrant energy of the island’s ‘cocina criolla’” on full display.
Location: 219 Calle Canals, San Juan, Puerto Rico 00907
El Vino Crudo
The first natural wine bar in Puerto Rico, El Vino Crudo will inspire you through drink and decor.
Location: 320 C. de la Fortaleza, San Juan, Puerto Rico 00901
Off the Beaten Path
The Island of Vieques
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.
Location: Vieques, Puerto Rico
La Parguera Fishing Village
Within the town of Lajas, you will find la Parguera, a fishing village-esque locale Valentin calls “a true local experience.”
Location: Lajas, Puerto Rico
Guavate in the Mountains of Cayey
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.
Location: Cayey, Puerto Rico
Whether you’re indulging in local cuisine, exploring hidden gems, or soaking up the sun on pristine beaches, Puerto Rico offers a diverse array of experiences for every traveler. Make sure to add these insider tips to your travel itinerary for an unforgettable adventure in this enchanting Caribbean paradise.
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