The Isle of Enchantment makes a comeback.

Forget everything “West Side Story” taught you about Puerto Rico. Once viewed as the backyard to the United States, this unincorporated territory (whose name literally translates to “rich port”) has undergone a luxurious resurgence of extravagant proportions, making this tropical island a top contender for high-end vacations and dreamy escapes.

Known as the Isle of Enchantment—and more importantly as the birthplace of the piña colada—Puerto Rico was claimed by Christopher Columbus for Spain in 1493 and has been a U.S. Territory since 1917. Although the island will thankfully always retain that sultry romance and Latin-influenced culture it has been known for throughout its history, the turnaround in the luxury market has led to Puerto Rico being dubbed the new Singapore of the Caribbean.

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Casa Lola's chef channels local legend Lola Milagros Cedeño in the restaurant's fare (photo courtesy of Casa Lola Restaurant)

The Commonwealth of Puerto Rico is nestled between the Dominican Republic and the U.S. Virgin Islands in the northeastern Caribbean on a 100-mile by 35-mile stretch of sand and shore. The island offers an intoxicating array of culinary delights, award-winning beaches, exquisite hotels, and definitive shopping and sightseeing options. Whether it’s soaking in the swagger of Old San Juan or socializing with the chic crowd in the Condado district, Puerto Rico’s old-world-meets-modern-luxury vibe keeps this island’s sultry culture cool year round.

BARRIO HOPPING

Much of Puerto Rico’s culture revolves around food, music and celebrating the country’s proud heritage … with more food and music, of course! To get a feel for the sites and stories that have shaped this island’s core, it’s best to start in the District of Old San Juan. This remarkable city was the first place the Spanish settled more than 400 years ago, and today acts as the historic hub where visitors can walk along the narrow cobblestoned streets to discover an array of boutique and name-brand shops, quaint cafes and hot new restaurants set inside colonial buildings that date back to the 1500s. The Spanish forts and castles in this area are a must visit, and any cigar aficionado would be amazed at the stunning selection of stogies at The Cigar House (www.thecigarhousepr.com) on Fortaleza Street.

The more modern neighborhood of Condado offers an entirely different view of the island, with luxurious homes, high-end shopping, and a trendy nightlife scene. Boutique shops like Louis Vuitton, Salvatore Ferragamo, Cartier and more line the breezy walkway down Ashford Avenue (also the place to head at night for live music and hand-crafted cocktails), while La Ventana al Mar offers a sweet spot to unwind in the open square and watch the sun set beyond Condado beach.

The Santurce district offers tons for art lovers, with the Museo de Arte de Puerto Rico (www.mapr.org/es)—an art museum that’s home to one of the most amazing collections of Puerto Rican masterpieces in the world—that is located just steps away from the Luis A Fèrre Performing Arts Center (www.cba.gobierno.pr), a hot spot for world-famous touring troupes performing the best scores of ballet and opera.

Local sportsmen recommend nothing else than the Trump International Golf Club (www.trumpgolfclubpuertorico.com) for a round of golf, the site of the Puerto Rico Open each year as well as a regular stop on the PGA tour, only to be followed by a treatment or two at the St. Regis Bahia Beach Resort’s famous Remède Spa (www.remede.com). When it comes to shopping on the island, Puerto Rico shines for its array of high-end jewelry, where the decade’s old, family-owned boutique E. Barquet (www.ebarquet.com) stands apart from the rest alongside the esteemed BARED Jewelers. The island is famous for mundillo, its hand-spun lace made with impeccable attention to detail and quality, and of course cigars and rum are a souvenir must on the island, with Bacardi and Don Q being the top sellers on the island. For a real treat, seek out Trigo Reserva Añeja, a small production rum that comes in a gorgeous hand-blown bottle with a wooden champagne-esque cork.

STAY-IN POWER

The coastline of Puerto Rico is a beautiful portrait of old meets new and natural meets metropolitan with sandy shores flowing seamlessly into both forests and city centers, and the luxurious resorts that weave in and out of the landscape only add to the scenic diversity. The island offers a unique blend of renowned high-end chains and upscale boutiques, both equally charming.

One of the largest resorts on the island is The Ritz-Carlton, San Juan (www.ritzcarlton.com), which is also coincidentally one of the most elegant options the island has for accommodations. Dark wood, cool marble and gilded details touch just about every corner of this Isla Verde location. The resort spans more than eight acres, set along sumptuously swimmable beachfront property and stocked with a dazzling casino on site and two decadent dining options, BLT Steak and Il Mulino New York. The resort is also home to a 12,000-square-foot spa offering local treatments like the Café con Leche Body Exfoliation, a detoxifying body scrub with the Caribbean fleur of Puerto Rican coffee.

In fitting with the island’s petite size, Puerto Rico also offers a few highly sought-after boutique sleeping experiences, with the Hotel El Convento (www.elconvento.com) standing apart as both the most glamorous and unique intimate-stay options on the island. The hotel is a member of Small Luxury Hotels of The World, and is set in a renovated yet well-preserved 17th-century convent. Antique touches like Andalusian tile floors and ornate handcrafted furniture are interspersed with modern amenities like flat panel TVs, goose down pillows and Bose radios, offering a taste of old-world charm without sacrificing modern luxuries.

Unlike most Caribbean destinations, not all of the top resorts in Puerto Rico are centered along the main coastal strip of lodging. Set 30-minute outside of the Old City, the St. Regis Bahia Beach Resort (www.stregisbahiabeach.com) is known more for its proximity to the El Yunque National Rain Forest and the Espíritu Santo River State Preserve than it is for its stunning spot along the shore (which just happens to be one of the most prime beaches on the northeastern corridor of the island). This secluded resort is situated on a former coconut plantation, and is a paradise for anyone looking to escape, featuring an 18-hole Robert Trent Jones, Jr.-designed golf course, a private bird sanctuary, local cuisine conceived by Chef Jean-Georges Vongerichten, and the amazing Remède Spa.

FARE PLAY

The only thing Puerto Ricans love more than dancing to local music and soaking in their spot in paradise is savoring the local delicacies of the island. The cuisine in Puerto Rico comes from an inspirational blend of Taino, Spanish and African influences, and includes rich recipes like carne guisada, alcapurria and pasteles. Although these classic dishes have been staples in homes on the island for generations, it’s only been recently that chefs have embraced these recipes and elevated them to gourmet status.

Chef Roberto Treviño spent most of his time competing and cooking his way through television channels, often appearing on shows on the Food Network and WIPR-TV, before opening his Condado hot spot Casa Lola (www.casalolarestaurant.com) where this celebrity chef is said to channel the cooking genius of local legend Lola Milagros Cedeño. Puerto Rico is no stranger to the celebrity chef, as Juan Jose Cuevas has settled back on the island with his new restaurant 1919 (www.1919restaurant.com) in Condado. A native Puerto Rican, Chef Cuevas has cooked in some of the most famous kitchens around the world and was named Chef de l’Avenir (Chef of the Future) by the International Academy of Gastronomy. Today, he offers an artisanal means for tasting and savoring the flavors of the island at his high-end eatery.

ROAST OF THE TOWN

Any trip to Puerto Rico would be remiss without a farewell sip of authentic, premium Puerto Rican coffee. Alto Grande has been called the Coffee of Kings and Popes, and rightly so as this rare and exotic coffee is often found on the breakfast trays in the Vatican and in numerous royal courts. The baristas at the St. Germain Bistro and Cafè (www.stgermainpr.com) certainly do this blend justice, also serving up another boutique bean called Quatro Sombras, and the bistro is perfect for a leisurely Sunday brunch before returning home after a dreamy trip to this island paradise.