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Finding Your Perfect Caribbean Island Resort: Insider’s Guide

Lindsey Epperly | February 16, 2017

The insider advice on this page is from Wendy’s Trusted Travel Expert for the Caribbean: Lindsey Epperly of Epperly Travel.

Trusted Travel Expert
Lindsey Epperly

Lindsey grew up visiting dozens of Caribbean islands on family vacations. Today she can guide you to the best destination and resort for your needs, saving you from costly logistical errors, overbuilt beaches, and cruise day-trippers. She believes that “every island has its own personality” and knows firsthand which are best for unplugging (Turks and Caicos) or adventure (St. Lucia), which appeal to culture and history lovers (the side-by-side French-Dutch mix of Saint Martin/Sint Maarten), and which deserve a better reputation than they currently have (Jamaica). Thanks to powerful industry connections, she gets special benefits and perks for her clients at a wide range of four- and five-star hotels, from “Old Caribbean” estates with a colonial feel to the slick, super-modern hotels that have been springing up lately to family-friendly all-inclusives to hidden-gem romantic retreats. For those wanting to do more than just laze on a beach, she can embellish your trip with snorkel excursions, zip-lining adventures, helicopter transfers, you name it. She has a particular knack for coordinating honeymoons and destination weddings (it’s not easy playing point between Type-A bride and a vendor working on “island time”).

Trips start at $400 per day for two travelers.
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Choosing the Right Island

Best beaches
Most people travel to the Caribbean to enjoy the beautiful beaches—the standard “fly and flop” vacation—and it’s certainly a perfect destination for that. While you can find inviting stretches of sand just about anywhere, the islands most famous for their beaches are what some call the coral islands: the Turks and Caicos, the Bahamas (Eleuthera, Harbour Island, and the Exumas are among the favorites), and Anguilla. These are all basically flat and scrubby with the quintessential powdery white sand and crystal-clear water that the Caribbean is famed for. For beach resorts that have raised pampering to an art form, try the brand new Four Seasons Anguilla, the Grace Bay Club and Parrot Cay in Turks and Caicos, or Tiamo Resort in the Bahamas, which is accessible only by boat or sea plane (and also happens to be one of the region’s best-kept secrets for bone fishing).

Four Seasons Anguilla

Pool view of the Four Seasons Anguilla. Photo: Four Seasons

Action and adrenaline islands
For those who get bored after a little bit of beach time, snorkeling and diving are always easy options in the Caribbean, but there are also plenty of islands where travelers can spend their days in active land-based pursuits. St. Lucia, Puerto Rico, and Jamaica, for instance, are all mountainous islands where visitors can hike, mountain bike, mountain climb, and zip-line. You can also hike a volcano, explore a rain forest, and get in some superb bird-watching at all of these. Hotels for active travelers include Anse Chastanet on St. Lucia, where you can choose from a menu of activities that includes yoga, tennis, snorkeling, scuba diving, sailing, sea kayaking, jungle biking, hiking, and bird-watching among the ruins of an 18th-century colonial plantation. Any of the Island Outpost properties in Jamaica (Goldeneye, Strawberry Hill, and the Caves) can arrange wildlife tours, excursions to underwater caves, hikes in the Blue Mountains—they’ll even take you to explore the island’s vibrant art and music scene and to visit the tenement yard where Bob Marley lived as a young man.

While Aruba is a bit commercialized, complete with chain restaurants and casinos, some travelers prefer a place where there’s more to do than just laze on the beach—and the Hyatt Regency and the Ritz-Carlton Aruba put you in the middle of it all. For an adults-only getaway a bit farther from the crowds (but near enough to still have fun), try the Bucuti & Tara Beach Resort.

Golf at the Four Seasons Nevis

Golf at the Four Seasons Nevis. Photo: Four Seasons.

Hidden gems
There are several islands that you can reach via nonstop flights from many U.S. cities. These are the more familiar and busy ones, including Jamaica, Puerto Rico, and the Dominican Republic. But to get to the really special places, you’ll have to put in a little more time and effort, which usually means at least two flights—one of them on a puddle jumper—and sometimes a ferry ride. The British Virgin Islands and Cayman Brac, along with St. Kitts and Nevis, are all well worth the effort it takes to reach them. The twin-island nation of St. Kitts and Nevis has lovely plantation-style inns such as Montpelier and Nisbet Plantation—both charming, small hotels that let you sit back, relax, and enjoy the tranquil surroundings. If you need a little more activity, the Four Seasons Nevis is a great choice for golfers and spa aficionados. Cayman Brac is just a quick flight from Grand Cayman, but a world away in terms of seclusion; Le Soleil D’Or is an incredibly charming place with just 11 rooms and a farm-to-table beachside experience.

Curacao does have nonstop flights from the U.S., but it’s less touristy than many other Caribbean islands. There’s wonderful scuba diving here, and a traditional Dutch influence—the charming, colorful buildings in the main town could just as easily be in Holland. It’s also home to the 23-room Baose Luxury Resort, the ultimate in barefoot luxury.

Luxurious getaways on iconic islands
Barbados is an incredibly clean island with an intact local culture, and it’s a bit wealthier than many of its neighbors, thanks largely to its years of consistent tourism. Luxury accommodations here range from the classic Sandy Lane, to the more boutique Sandpiper, to knock-your-socks-off villa rentals. Rosewood’s Jumby Bay Resort on Antigua, ringed by 4.5 miles of palm-fringed beach, is about as indulgent as it gets.

Hermitage Bay, Antigua

Hermitage Bay on Antigua is perfect for a romantic getaway. Photo: Hermitage Bay Resort

Islands for romance
The Caribbean has all the ingredients for a romantic getaway, including some small, charming hotels on glorious beaches: Hermitage Bay on Antigua, where the airy, hillside pool suites offer complete privacy and stunning views of the sea; the Jamaica Inn, in Ocho Rios, which has an elegant, old-world feel and rooms just steps from the surf; and Taïwana, a secluded and intimate St. Barth’s hotel on Flamands Bay with 22 individually designed rooms and suites that offer every luxury. At Jade Mountain, on St. Lucia, the huge rooms (called “sanctuaries”—which gives you a sense of how private they are) seem to cling to the hillside above the beach, with incomparable views of the Pitons. These rooms have only three walls, so the fresh sea breezes can waft right in, and no phones or TVs. The service is impeccable—your majordomo will make sure you and your honey have everything you need.

When you want to be alone
Those seeking privacy and seclusion can choose from several resorts on their own private islands. Parrot Cay (Turks and Caicos) sits on a 1,000-acre unspoiled island and features a mile-long white-sand beach. Rosewood’s Jumby Bay Resort on Antigua is ringed by 4.5 miles of palm-fringed beach. (Both also have beautiful rental villas that let you have complete privacy but also enjoy the facilities of the hotel.)

Curtain Bluff resort in Antigua & Barbuda caribbean

The beautiful Curtain Bluff, Antigua & Barbuda. Photo: Lindsey Epperly

Family-friendly islands
Once mostly mediocre meccas for the masses, all-inclusive resorts have improved significantly in recent years and are now a great option for families. Some of the better choices include the Paradisus resorts in the Dominican Republic and on Mexico’s Yucatan Peninsula. One of my favorites is Curtain Bluff on Antigua. This gem has 72 rooms and suites and has been owned and operated by the same people for years. They were all-inclusive before anyone really knew what the term meant, and they have an unbelievably high repeat-guest ratio—it’s not uncommon to meet people on the beach who have been traveling to Curtain Bluff for 25 years. Guests here are made to feel like returning friends. The property sits on two beautiful beaches—one ideal for swimming and water sports, the other more of a surf beach—and offers activities (including a championship tennis center) for everyone in the family.  With the exception of a few over-the-top luxuries (Cuban cigars, vintage wines) and spa treatments, everything is included in the rate.

Passport-free getaway
Want a luxurious Caribbean beach vacation without the hassle of going through customs? Of all the territories one can travel to in the Caribbean without a passport, the fanciest options are found in Puerto Rico, at the Ritz-Carlton Dorado Beach and the St. Regis Bahia Beach. For a bit more character with your five stars, try the Condado Vanderbilt, which is hands-down the most historic retreat on the island—and arguably the best bang for your buck.

Not your parents’ Caribbean
Several hotels have opened in the past few years that have departed from the traditional Caribbean style. These include St. Lucia’s sleek Sugar Beach and Amanyara in the Turks and Caicos.

Aman Resorts’ Caribbean outpost, Amanyara, is a pricey but perfect luxury option set on a secluded beach outside busy Grace Bay, on the island of Providenciales in the Turks and Caicos. The property features 40 villas and pavilions in a pared-down contemporary design—along with the legendary Aman service. Discrete and private: a perfect combination.

Sugar beach

Beautiful pool steps from Sugar beach. Photo: Lindsey Epperly

A multimillion-dollar renovation has given Sugar Beach a modern vibe without stepping on the toes of its Caribbean heritage. The bungalows and cottages look Caribbean on the outside but, on the inside, everything is a crisp, airy white that feels almost otherworldly.

Traditional island charm
In spite of decades of development and rising tourist numbers, the “classic Caribbean,” happily, can still be found. Relaxed and low-key, St. Kitts and Nevis have small, lovely hotels and plantation-style inns that harken back to a quieter time when whaling ships plied the waters just off shore, such as, Nisbet Plantation on Nevis, which has great personality and offers warm hospitality and service.

Where to Eat and Drink

Caribbean seafood

The Caribbean is known for its great seafood. Photo: Hermitage Bay Resort

Best beach restaurants and bars
Islands like Anguilla, St. Lucia, Turks and Caicos, and Barbados now feature multiple fine dining spots as well as wonderfully fun and casual beach “shacks” where you can happily spend the afternoon dining on regional specialties and sipping the local hooch at the edge of a beautiful beach. Sunshine’s sits on Nevis’s Pinney Beach and is famous for its “Killer Bee” rum punch—the recipe is practically a state secret! On Anguilla, Bankie Banx’s Dune Preserve’s potent signature beverage is called Duneshine. Foxy’s, on Jost van Dyke in the British Virgin Islands, was founded by the self-proclaimed laziest man on earth and is home to a legendary New Year’s Eve party. Maybe the most unusual experience can be found at St. Maarten’s Sunset Bar and Grill, where you basically sit at the end of the airport runway—and under arriving aircraft—while you sip your drink.

Must-have dishes
Several islands have “must try” dishes for which they’re famous. In the Bahamas and Turks and Caicos, it’s conch: pounded; fried; frittered; grilled; in salads, chowders and stews—any way you try it is delicious. (Be sure to try da Conch Shack, on Providenciales in the Turks and Caicos, and the Flying Fish, in Barbados.) Jamaica’s specialty is jerk chicken, fish, pork—and goat. Jerk is a process of marinating meat in potent spices for 24 hours and then cooking it on a barbecue.

 

Best Times to Go

The weather in the Caribbean is pretty consistent, with temperatures varying little year-round, though there’s more humidity and a greater chance of afternoon showers from April through October. May, June, July, November, and early December are great times to visit when you can enjoy substantial savings off peak-season rates, which are in effect from just before Christmas until just after Easter. Low season starts in earnest on May 1, when hotels drop their prices by as much as 40 percent and also often offer free nights and other incentives.

Worst Times to Go

Hurricane season officially begins on June 1 and ends November 30. Many hotels close as the season begins to peak at the end of August and don’t reopen until mid-October or the end of the month. This can still be a good time to visit, but be sure to buy “cancel for any reason” insurance, which allows you to cancel your trip up to the last minute and protects you from losing your investment if a storm does sweep by.

Biggest Rookie Mistake

Check the expiration date on your passport—it gets risky when you get to the six-month mark. Most countries now require you to have a passport that will be valid for at least three to six months from the time you travel or they won’t admit you—not a nice surprise at the check-in counter!

 

Reviews

Very experienced, knowledgeable

Andy Robinson | May 25, 2017

Within 3 days

David Nethero | March 28, 2017

Details to facilitate a decision

JoAnn Hofheimer | February 16, 2017
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