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


If Bad Bunny’s Super Bowl halftime show taught us anything, it’s that Puerto Rico is more than a getaway. It’s a way of life.

Vivir a lo boricua took center stage as the Levi’s Stadium was transformed into scenes inspired by the Caribbean island (and Nuevayol)—right down to Toñita’s Social Club in Brooklyn.

Sung almost entirely in Spanish, the Grammy Award-winning artist belted his heart out, matching the rhythm of what makes Puerto Rico, Puerto Rico. Joining Bad Bunny was Ricky Martin, along with “Tití Gaga,” who salsaed her way across the stage in a baby blue Luar dress by Dominican-American designer Raul Lopez. All of the Americas even got a shoutout, culminating in a powerful sentiment: The only thing more powerful than hate is love.

Nearly 135 million viewers tuned in, breaking the record as the most-watched halftime show of all time. So if booking a flight to San Juan crossed your mind, chances are you weren’t alone.

My own 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. While visiting my family in Cayey, I heard stories about how loud the winds were. 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 dominoes at my grandfather’s house, and fresh papaya plucked from my 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 long since regained its old-world charm and contemporary flair. According to Discover Puerto Rico, the island continues to thrive, welcoming approximately 7.5 million visitors in 2024, resulting in a total economic impact of $18 billion. “In 2025, Puerto Rico reached new heights, reaffirming the island’s place as a premier global destination,” said Storm Tussey, chief executive officer of Discover Puerto Rico.

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 Velázquez, 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 Velázquez. “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 are praising me for making it safely home to the motherland.”

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

It’s also a 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.”

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. And as Benito reminded us, remember to tirar más fotos.

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.



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