For many sun-worshipers, Puerto Rico might seem like the been-there, done-that of destinations on the Caribbean Sea. With its close proximity to the East Coast (three-hour flight from New York) and affordable airfares (as low as $200), the “enchanted island” is an obvious choice for travelers in need of a quick escape. But don’t let its familiarity fool you. With so much to offer—from dense rainforests and turquoise waters to trendy lounges and inviting casinos—many happy returns are in order. And if you haven’t been yet, what are you waiting for?
The first time I visited was the summer after high school graduation, more than 10 years ago. A classmate and I went to San Juan for a weeklong vacation that turned into a month-long stay. We snuck into the pool of the revered El San Juan Hotel & Casino; trolled along the cobblestone streets of the old part of town; became friends with the bartenders at the now defunct mega-club Peggy Sue; and had a regular table at Lupis (a nacho-serving beach hut in the touristy sector of Isla Verde).
A decade later my girlfriend and I returned—just as reggaeton (popular Spanish dancehall music that flourished in PR) was seeping out of the ghetto and into the mainstream—and became reacquainted with another side of the island. We hiked among the 240 species of trees and plants of El Yunque, a 28,000-acre tropical forest located in Luquillo, an hour from San Juan. There we explored the lush foliage and bathed in spectacular waterfalls. We headed Fajardo’s bioluminescent bay, where we kayaked under a midnight blue sky and flapped around the water, awakening microscopic organisms that light up when they sense predators. We drove north to Rincon and, as the sun hit the water, shared beers and stories with surfers who flock to this wave-lovers’ corner from all over the world. (This took us several days but you can circle the entire island by car in less than 24 hours.)
Of course, this rekindling did not come without some high-stakes entertainment. Most big hotels in Puerto Rico share one activity in common: gambling. And as career women we now had some money to play with. At the Radisson Ambassador Plaza Hotel & Casino, located on a strip of hotels in the touristy area of Condado, we spent eight hours at a craps table hoping not to see the dreaded seven roll of the dice. There we sipped Dom Perignon with an Indecent Proposal-style businessman from St. Thomas, who stopped by our table to say hello and left with just a greeting and minus $4,000. We returned to our room with a buzz and a profit of $130 (equal to a night at the Radisson) between the both of us.
During my last sojourn to Puerto Rico, a few weeks ago, I was in search of relaxation. This time around I stayed with friends in Rio Piedras, a suburb of San Juan. I did like the residents do and sunbathed (Corona in hand) at Ocean Park Beach, a white patch of sand where beautiful Puerto Ricans work on their tans. That night, after acquiring some of the local color, a few friends and I downed four bottles of Chianti at Ventanas al Mar (windows to the sea), a Miami-esque outdoor lounge overlooking the water in Condado, where folks of all ages mingle and flirt. The ladies were definitely a sight to behold: mostly longhaired beauties dressed in short skirts or low-rider jeans. While the men—content that there were seven women for each of them—happily sat back and watched the parade of lip-gloss.
The next day we drove to the marina in Fajardo, on the eastern coast of the island, where one of my hosts took out his boat for a daytrip to Culebrita, an islet next to Culebra, a larger island that, from afar, resembles a giant snake lazing about. Floating on clear azure waters while sipping Medallas, the country’s cerveza, I realized that no matter how many times I had visited this little piece of the world, I would be back. That evening, at King’s Seafood, a modest after-beach hang serving fresh fish in Luquillo, I ate mofongo (a national dish made of mashed plantains, garlic, and meat, chicken, or seafood) with octopus—and had a few more Medallas.
I know, I know, been there, done that—and can’t wait to do it again.