Why Puerto Rico is the Most Underrated Tropical Destination

July 29, 2019

Before you choose your next Caribbean vacation, scribble a list of what you’re after on a piece of paper. It might go something like this: shimmering seas and sugar-sand beaches; balmy weather; breezy luxury accommodations; surfing, diving, sailing, jungle hiking, and a round of golf; food culture, including a rum or three; a touch of the exotic; and, since you’re headed to the Caribbean, not the South Pacific or Asia, easy access.

Next, off the top of your head, pin some destinations to those desires. Turks and Caicos have some of the most sparkling beaches in the West Indies. St. Lucia is swathed in jungle and exploding with mountains for tropical adventures. Cuba is a cultural time capsule. The Caymans have teeming reefs and vibrant waters. But if you want to roll all those elements into one destination and make it as easy to get to as flying to Miami, there’s only one place to go, Puerto Rico—the United States’ nearest tropical escape and perhaps one of the most overlooked destinations in the Caribbean. 

The Dominican Republic, Jamaica, the Bahamas, and the Mexican Riviera often draw more travelers annually. And where Curaçao conjures visions of beach cocktails and Saba or Montserrat sound as exotic as the South Pacific, for Americans, Puerto Rico often evokes the mainland; it’s too close and too easy to feel like a true escape. “Those associations are understandable, but I don’t see it that way,” says Mari Jo Laborde, chief sales and marketing officer at the Puerto Rico Tourism Company. “The fact that we are part of the U.S. means that travelers can get here quickly and easily without the headaches of a passport or immigration. But the island is a whole different culture than anything on the mainland, and we have more diversity of things to do than any other place in the Caribbean.” And judging by recent trends, Puerto Rico’s stature might be on the rise. 

Though the slump in tourism that washed over the Caribbean after the economic crisis in 2007 hit Puerto Rico hard, visits to the island have been on a steady rise since 2011. “There has been a major reinvestment in hotels and infrastructure in the last few years,” Laborde explains. “We’re also seeing a resurgence in the luxury market and a renewed effort to recapture some of the old glamour that started in the 1920s and lasted through the 1950s.” 

The idea of Puerto Rico as an exclusive escape isn’t something new: In the 1920s, the island was once considered as exotic as Hawaii and as glamorous as St. Tropez. Even then, Dorado Beach sat at the heart of that dazzle. The property was a citrus and coconut plantation owned by New York physician Alfred Livingston. It was Livingston’s daughter, Clara, the 200th female pilot in the world, who brought celebrity to the place. Clara’s good friend Amelia Earhart visited occasionally, including an overnight in 1937 on the first leg of her fateful attempt to circumnavigate the globe. Laurance Rockefeller purchased Dorado Beach and opened it as a hotel in 1958. It was a prescient venture. 

Around the same time, hostilities fired up between Cuba and the United States, and the socialites and Hollywood stars who were frequenting Havana as a playground suddenly turned to Puerto Rico. Elizabeth Taylor, Ava Gardner, Joan Crawford, and presidents Eisenhower and Kennedy all visited during the heyday 

It’s this Golden Age mystique that Ritz-Carlton is chasing with the reopening of Dorado Beach. The hotel owners spent $342 million on the project and crafted a property befitting its celebrity past. It tapped Spanish culinary phenom José Andrés to run Mi Casa, the gourmet Puerto Rican-fusion restaurant on property, and brought in Jean Michel Cousteau’s Ambassadors of the Environment program to guide its diving and underwater ecology programs. The property is an Eden of lush waterfalls and gardens, and the bungalows and suites, which are tucked beneath the old growth trees and coconut palms redolent of the Livingston days, feel as if they’ve been there for centuries.

Helbling will tell you that the time is ripe for a tourism boom in Puerto Rico. In the past five years, the Puerto Rican government has instituted a generous program of tax and housing incentives to lure investors and high-net-worth individuals to move to the island. Plans are afoot for a major renovation to the airport at San Juan that will accommodate new routes from the mainland. “We now have direct flights to most major cities: New York, Washington D.C., several airports in Florida, Chicago, Houston,” says Laborde. “In just three or four hours from home, you can be on the beach. That’s less time than many Americans spend commuting each day.”

The payoff for that short vacation commute to Puerto Rico is an island packed with history, culture and natural beauty. The island’s history starts at the centuries-old stone fortifications and bluestone cobbled streets of the old city that transport visitors into a different time and culture. First stop, a stroll atop the ramparts of El Morro, the walled fortress built on the high promontory overlooking San Juan Bay, which evokes 400 years of Spanish rule and all its history. The island’s modern history dates to 1952, when Puerto Rico became a United States commonwealth. Just outside the ramparts, a World Heritage site since 1983, the narrow grid of streets is packed with cafés, galleries, antique shops, stone plazas, and hundreds of pastel-splashed 16th- and 17th-century Spanish Colonial buildings that have been fully restored. Officially this is America, but it’s arguably the most exotic and authentic corner of the Union this side of Santa Fe, New Mexico.

After dark, the streets echo with live salsa music, the brassy screech of horns and incessant thrum of pianos and congas dancing off the ancient streets. Outside the time capsule of Old San Juan, however, the quaint little corners of this city of more than 2 million, half the island’s population, have sprung to life in recent years. Condado, once a tacky touristy strip of hotels east of the old town, has been resurrected with boutiques amid lush, tree-shaded parks. The gorgeous renovation of the beachfront Vanderbilt Hotel, originally built in 1919 and host to no less than Bob Hope, Errol Flynn, and president Franklin D. Roosevelt, has only added to the district’s renaissance. Ocean Park, at the east end of Condado, draws discriminating visitors with luxury guest houses and one of the hippest beaches in the city. And straight south is Santurce, a slightly gritty working class neighborhood that’s becoming the Chelsea of San Juan as it fills with trendy 20-somethings and cutting-edge galleries showcasing contemporary Puerto Rican art.

It would be regrettable to miss out on the sexy, Spanish influenced, metropolitan side of Puerto Rico, but talk to anyone who lives there, and they’ll tell you that much of the island’s charm lies outside San Juan. “Visitors should really explore the rest of the island,” says Chelsea Harms, a marine scientist who lives on the west coast and author of the lifestyle and travel blog Sea, Field, and Tribe that documents life on this Caribbean outpost. “Outside the metro area, you get a better feel for how different this place is from the rest of America.” The quickest introduction is along La Ruta Panorámica, the island’s answer to Maui’s Hana Highway, with 165 miles of meandering switchbacks through the countryside. The road— it’s actually a linkage of 40 secondary roads—traverses Puerto Rico’s central spine through heavily forested hill country from Maunabo in the east to Mayagüez in the west. Though it’s not even an hour’s drive from the capital, this Puerto Rico is a lifetime removed from Dorado Beach, with field-workers harvesting sugarcane in the humid south, verdant coffee plantations in the highlands, and chickens and goats to dodge the whole way. A blanket of rain forest that looks like broccoli from a distance covers most hills, and, for the intrepid, trails that dead-end at deserted waterfalls speckle the countryside.

Near the end of La Ruta Panorámica, on the snout-shaped peninsula at the island’s northwest tip, sits Rincón, a dozy town of 15,000 whose population multiplies during the winter surfing season. The place gained a bit of an international reputation in 1968, when the World Surfing Championships came to town. Since then it’s lured surfers from all over the globe with stretches of lonely sand and swells that can reach 25 to 30 feet. CNN Travel rated it No. 27 on the list of world’s best 50 places to surf. It’s the laidback opposite of San Juan, with good waves and pristine reefs and a far-flung vibe quite apart from Laguna Beach or Nags Head. Harms agrees that it’s the chilled-out West Indies attitude that draws people. “It’s just a friendly little beach town,” she says of her adoptive town of Rincón. “You can walk to the beach from your house, leave the windows and doors open for the breeze, and basically have the best ocean, from the surf to the reefs, this side of Hawaii.”

A Personal Vacation Advisor's List

Eat: Don’t miss the award-winning wine list and dishes such as freshly made gnocchi with organic beef tenderloin in a cabernet sauvignon sauce at Marmalade Restaurant in Old San Juan. // Stay close to home for a Caribbean spin on Italian cuisine at the Grappa Ristorante in Dorado. Try the fresh, locally sourced grouper served over wild mushroom risotto.  

Explore: Set off in a kayak or paddle board for the full moon paddle departing from Cafe Barlovento in Condado. // Visit the El Yunque National Forest, the only rainforest on U.S. soil. Well-marked paths lead to waterfalls and observation towers scattered throughout the park. //  Inspirato’s residences are located inside the Ritz-Carlton Reserve at Dorado Beach, a 45-minute drive from the San Juan International Airport. Vacationers can choose from either a multi story penthouse with four bedrooms and a 2,700-square-foot private terrace, or a fourth-floor, three-bedroom condominium residence. Both are situated within the exclusive Plantation community along the golf course’s renowned fairways with views of the mountains and ocean. // First Sunday of every month Mercado Urbano Head to La Ventana del Mar in Condado where more than 40 farmers and artisans from across the island sell their wares.