One of the standout moments of Bad Bunny‘s Super Bowl halftime show this past February was when he shouted out every country of the Americas, punctuating it with “Canadá!”—a small but oddly thrilling moment of inclusion for we Canadians. It turns out Puerto Ricans took note, too. On my recent trip to Puerto Rico, it came up almost every time I mentioned where I was from.

For a relatively small island—roughly two and a half times the size of P.E.I.—Puerto Rico casts a surprisingly long cultural shadow. It’s one of the birthplaces of reggaeton, now a global pop force, and home to the world’s largest rum distillery, just across the bay from Old San Juan. And then there’s Bad Bunny, whose rise to global superstardom has only amplified the island’s cultural reach.

Like a drop of dye spreading through water, his influence has rippled across Puerto Rico—not just culturally, but economically, too. His 2025 31-show residency is widely credited with boosting tourism, generating hundreds of millions in visitor spending and global attention. According to Discover Puerto Rico, the island has now seen record tourism numbers for six consecutive years, with searches for Puerto Rico jumping more than 200 percent in the days following the Super Bowl. More broadly, he has come to represent a modern Puerto Rican identity, one that now stretches across music, nightlife, and even the island’s food scene.

It’s something you hear from people on the ground, too. Michael, one of our drivers, admitted he wasn’t always a fan of Bad Bunny, but said the residency changed his perspective (a sentiment I heard multiple times). He recalled seeing Mexican fans arrive dressed head-to-toe in Puerto Rican colours. “They were so into it,” he said. “That’s when you realize how positive it is. He’s bringing people together—getting people interested in the island, the culture, everything.”

My stay, just a seven-minute drive from Luis Muñoz Marín International Airport, was at the Fairmont El San Juan Hotel, a resort that first opened its doors in 1958. It’s steeped in mid-century Caribbean glamour: marble floors, hand-carved wood ceilings, and a 7,000-piece Czech crystal chandelier suspended above the bar at the centre of the lobby.

Large chain resorts can often feel cut off from the place you’re visiting (a bit like drinking Starbucks in Italy), but the El San Juan feels plugged into the city. The lobby has long functioned as a social hub, with a steady stream of live performances on its stage and a legacy nightclub that still draws a local crowd. It’s easy to see why it’s been nicknamed San Juan’s living room. The lobby was bumping every night—with guests dancing between tables and at the bar in addition to the actual dance floors.

By late morning the next day, the energy on the blue cobbled streets of Old San Juan revealed a different rhythm altogether. The neighbourhood’s soft blues, yellows, and pinks, along with its Spanish colonial architecture, give it a calming feel by day. Walking through the neighbourhood with guide Christian Santiago of Turismo Borincano, the story of reggaeton begins to take shape as he takes me from the sites of historic clubs over to La Perla, the seaside “favela” made famous by the “Despacito” video—and a place best explored with someone who knows it well.

There was a time, Santiago explained, when reggaeton wasn’t the global force it is today. Like gangsta rap in the early ’90s, it was rooted in youth culture and often dismissed by older generations as vulgar. Today, it’s the island’s most recognizable cultural export, propelled in no small part by figures like Bad Bunny.

At Lala, which Bad Bunny co-owns, chef Guillermo López Folch—a former student of Eric Ripert of Manhattan’s Le Bernardin—the hospitality is without question Puerto Rican, while the menu leans more Mediterranean-Asian: manchego croquettes, Angus beef gyoza, short rib tortellini, and whole fish and meats grilled over Japanese charcoal.

It’s just one restaurant expressing the country’s confidence. For a deeper look at the island’s culinary roots, there may be no better stop than Cocina al Fondo. Here, Natalia Vallejo, a James Beard Award winner, reinterprets traditional Puerto Rican dishes in modern ways. The menu draws heavily on local ingredients and long-standing techniques, all served in a homey setting with a back patio where you can hear the island’s famous coquí tree frogs.

Even on a tour of the Bacardi distillery, the six-time Grammy Award-winner’s influence is felt. Our guide Christian Frontanés told me the company created pre-concert experiences timed to coincide with the residency. “Because of the residency, now we have Shakira coming this year,” he said. “Artists we never expected to see here before. And now, because of Bad Bunny, we’re seeing that shift.”

It doesn’t take long for the landscape to change when you leave San Juan behind. The roads are safe and the distances short. Heading south toward Ponce, about halfway, I passed through the mountain town Cayey. It was here, on the balcony of the Casa Histórica de la Música, that Bad Bunny announced his sixth album Debí Tirar Más Fotos with an impromptu performance that sent waves through the island, quickly filling the space and the streets outside. When I stepped inside, the centre was still active, hosting a small but lively afternoon gathering: food, drinks, and a live performance of traditional music.

In Ponce, the island’s second city, you’ll find broad plazas and stately architecture. The red-and-black striped Parque de Bombas firehouse—one of the city’s most recognizable landmarks, where the Ponce Municipal band plays weekly free performances and has been doing so for more than 140 years. The city is often associated with Plena, a style that emerged in the early 20th century in which singers narrated everyday life and current events. Sound familiar? It’s a style that has been a major influence on Bad Bunny’s music.

Another day-trip is a short drive east of San Juan to Loíza, long considered one of the cultural hearts of Afro–Puerto Rican life. Here it’s mangroves, beaches, and delicious roadside food stands. Here, the rhythms of Bomba—a centuries-old style built around call-and-response singing, barrel drums, and improvised dancing—still shape community gatherings and festivals.

On my last night, back in Old San Juan at the legendary La Factoría, a bartender slid an expertly made rum cocktail across the counter. Outside, rain fell steadily, but it did little to slow anyone down. Downstairs, it was salsa and dancing; upstairs, the DJs played house. In some ways, it reminded me of my youth, drifting through loft parties and after-hours spots in Montreal. It was an energy that felt loose and unforced.

Over a few days on the island, it became clear that Puerto Rico’s energy doesn’t come from any one place or person—even someone as massive as Bad Bunny—but from the people throughout it. What he’s done is amplify something that was already there: the music, the culture, and a distinct warmth. Now the world is finally beginning to tune in.

Images courtesy of Discover Porto Rico.