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Puerto Rico is having a moment, albeit not for the first time. The 2017 bop ”Despacito” encouraged more than a few internet searches to the destination, as did Hurricane Maria in 2019 (you’ll be glad to know the island has largely recovered).
But thanks to one of the world’s most-streamed Puerto Rican artists and his particularly buzzy Super Bowl LX halftime show, the U.S. territory has been catapulted into the cultural zeitgeist again, receiving a massive surge of interest with search terms like “flights to San Juan” increasing by 245 percent in the 72 hours following the show.
That adds up to a lot of people. But there’s a way to experience what the island of enchantment has to offer beyond its capital and away from the masses: get yourself on a helicopter.
I don’t mean actually buying a helicopter. (But if you have it like that, congratulations on some great life choices.) For most of us, though, that will mean enlisting the services of an aviation company, which, admittedly, might also sound out of reach. Here’s the great news: not necessarily. You can crisscross the island, observing the city sights of San Juan, the Bacardi rum distillery in Cataño, Bayamon’s science park, and Naranjito’s cable bridge for $300, or you can up the ante with an airborn chinchorreo—the Puerto Rican term for bar hopping with friends—that takes you from an asador in the mountains to a famed rum distillery along the coastal plains for $1,500.
Setting up base camp
I opted to maximize my bougie-adjacent chinchorreo experience with a stay at the Four Seasons Resort and Residences Puerto Rico, located in the municipality of Rio Grande, about a 35-minute drive from Luis Muñoz Marín International Airport and San Juan.
One of the things I loved about the property—aside from those legendary Four Seasons mattresses and sheets—is the on-site pet shelter that’s run in partnership with Alma de Bahía Foundation, a nonprofit focused on environmental conservation that has made helping the 300,000 strays in Puerto Rico one of its missions.
In Rio Grande, that effort takes place at the Four Season’s pet shelter, where pups and felines are vaccinated before they become available for guests of the resort to foster for a few hours. That might mean taking them for strolls on the beach or simply snuggling up with them in the resort’s pet-friendly rooms—a win-win for travelers missing their doggos and the pups who need a bit of love and socialization. And if you happen to fall in love (a mixed breed duo going by Shrek and Donkey were pulling at my heartstrings… hard), you can adopt your new four-legged soul mate, and the foundation will cover the cost of adoption and the flight back home for a donation.
Aside from providing some delicious doggie snuggles, the Four Seasons can also coordinate your helicopter adventure throughout the island.
Boarding the helicopter in San Juan
If you’re staying off-property, though, you’ll want to contact Puerto Rico Helitours, a local aviation company based in San Juan that’s run by a former police officer/pilot with Puerto Rico’s Air Unit-FURA and an engineer. As someone with a healthy fear of flying (not the best quality to have as a travel writer, I know), I felt I was in good hands.
The helicopter itself is small, but comfortably seats the pilot, a passenger to their left, and one more tagalong in the back seat. If you’re looking for maximum views, claiming the front seat will accomplish that in spades—the floor-to-ceiling window feels like you're hovering in a bubble, gently bobbing through the sky.
Departing from San Juan, the helicopter steadily loped its way around the coast, hugging the shoreline from the sky and offering birdseye views of Castillo San Felipe del Morro, La Fortaleza, and dozens of resorts spilling out into the turquoise Caribbean waters. The pilot pointed out several key spots to watch for as the chopper climbed steadily higher into the sky.
A 10-minute flight to cotton candy martinis in the mountains
The first stop on the flight was Asador San Miguel, a rustic grill up in the mountains of Naranjito, known for its cotton-candy-topped cocktails, grilled proteins, and flaming (literally) queso kasseri. The trip, which would have taken nearly two hours by car, lasted for 12 minutes before our helicopter found a landing pad in a soft patch of earth within walking distance of the restaurant. The asador’s mountain top perch not only afforded us 360-degree views of Puerto Rico below, but dropped the temp a good 10-15 degrees—not a bad perk when flying on an 85-degree day.
Sipping rum old fashioneds in the coastal plains
After boarding our helicopters, we flew over verdant mountain tops with views of El Yunque rainforest before landing at Hacienda Santa Ana in Bayamon, the home of the island’s beloved Ron de Barrilito. The Hacienda is over 145 years old, and has been blending and aging rums since 1880, a fact you’ll pick up on the tour and tasting. But at the end of the experience, Ron de Barrilito’s bar and outdoor garden are waiting for you, and the bartenders here are no slouches. There’s the requisite piña coladas, but the bar really hits its stride when it comes to their menu of rum old-fashioneds, of which you’ll find the classic along with riffs that incorporate things like coconut foam, tobacco bitters, and smoked domes.
The hacienda’s garden patio looks directly out onto a grassy esplanade, where the helicopter awaits. After a few of Barrilito’s cocktails, we boarded our choppers in front of the hacienda’s visiting tourists, feeling like celebs jet-setting to a private villa.
Flying back to Puerto Rico Helitour’s base in San Juan was a quick 10 minutes that maneuvered us around one of the island’s afternoon downpours. Even with the threat of torrential rain, the ride felt smooth and effortless—our pilots confidently navigating around the weather to avoid any uncomfortable bumps or safety issues.
It’s well worth stepping outside of San Juan to experience a taste (and sip) of what the different regions of Puerto Rico have to offer. Sure, you can rent a car, but you might find that after adding up the travel expenses and experiential cost of time spent driving around the island, stuck in traffic, or inclement weather, catching a ride in a helicopter might pay off after all.