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Best and Worst of the Caribbean: Insider’s Guide to Beach Vacations

Lindsey Epperly | September 15, 2016

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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Things to Do in the Caribbean Islands

Most overrated experience
Most Caribbean cruises barely scratch the surface of the islands, relegating you to crowded, sometimes even dirty ports, and giving you way too little time in the nicer ones. They’re a solution for the traveler who wants to island-hop without the logistics—but only if you choose the right itinerary on a smaller ship.

Pool view of the Four Seasons, Anguilla, caribbean islands

Pool view of the Four Seasons, Anguilla. Photo: Lindsey Epperly

Most underrated experience
Antigua isn’t on many travelers’ radar, but it should be: The people are incredibly friendly, the beaches sugary white, the water almost as bright blue as in the Turks and Caicos, and there are a number of fantastic hotels. Flight schedules aren’t always ideal, but it’s well worth the effort of getting there.

Hidden gem
The Out Islands of the Bahamas are some of the best undiscovered treasures in the Caribbean. Imagine a world where there are only golf carts, pristine beaches, surprisingly elegant accommodations, and fine dining. Don’t think it exists? Look no further than Harbour Island.

Cheap thrill
The Island Vibes half-day snorkeling tour in Turks and Caicos: For $89 (half that for children three to ten years old), guests staying on Grace Bay Beach are picked up at their hotel and taken to snorkel first at the world’s third-largest barrier reef, then in the crystal-clear water of the Turks and Caicos cays. You get a bit of culture with your wildlife, too: The guides will show you how they farm for conch (an island delicacy), then crack one open to make a fresh conch salad right on the boat.

Sugar beach

Sugar beach. Photo: Lindsey Epperly

How to spend a lazy Sunday
Many Caribbean islands are deeply rooted in the Christian faith, which means Sunday sees closures of attractions, shops, and even restaurants. So blow up your pool float (see Don’t Forget to Pack) and hit the beach. Depending on the island, consider venturing from your resort to a public beach to hang with the locals: On St. Barts, for instance, the public beaches (especially Gouverneur and Saline Beach) are postcard-perfect.

Where to Stay

Best-value splurge hotel
A 300-acre private island off the coast of Antigua, Jumby Bay is a truly all-inclusive five-star experience that never leaves guests feeling nickel-and-dimed. The rate covers all meals, drinks, and many on-site activities that at competing properties incur a surcharge (think snorkeling excursions, nature hikes, and cooking classes). People who book through me get a $100 spa credit per room, plus upgrades, early check-in, and late checkout when available.

Jumby Bay Antigua

Jumby Bay Antigua. Photo: Lindsey Epperly

What to Eat

Restaurant the locals love
Sunshines: A short walk from the Four Seasons Nevis, this little beach shack is famous for its Killer Bee rum punch. And food doesn’t get any fresher than the grilled lobster, which you’ll see the staff hauling in during the season.

The Oistins Fish Fry: Every Friday night in Barbados, stand after stand of local restaurateurs set up shop in the fishing town of Oistins. Both the fried flying fish—an island favorite—and the grilled lobster go great with a cold beer.

Scotchie’s: This Jamaican staple with locations in Montego Bay and Ocho Rios is known for its jerk chicken and pork, but don’t overlook the freshly made smoothies.

Treats to try
Creole bread in St. Lucia. The finest version of this freshly baked French-style baguette is served at a roadside stand that all the locals know about yet is easily overlooked by tourists—even though it’s on the way from the airport to most of the major resorts. The bread is served warm with your choice of butter or cheese to melt in the middle.

Sky juice in the Bahamas,. This mix of evaporated milk, gin, and coconut water is reminiscent of a melted piña colada but not as sweet, making it dangerously easy to enjoy more than one.

Meal worth the splurge
Dasheene, at Ladera Resort on St. Lucia, serves cuisine that offers a deep sense of place, with a masterful gastronomic spin on local favorites. Like most of this hillside resort, the restaurant is open to the elements, with dramatic views of the Piton Mountains.

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Best Times to Go

Late May or early June. You get great weather but fewer visitors and lower prices. (The high season lasts through the end of April, sometimes even into early May).

Worst Times to Go

The Christmas–New Year’s school break. As lovely as a sunny Christmas or a New Year’s under the palms might sound, you should expect hotel rates that are 25–50% higher than usual, paired with minimum stays of seven or more nights. The high prices often lead to higher expectations, yet the bursting-at-the-seams crowds leave many a resort’s staff stretched thin, so service suffers.

Biggest Rookie Mistake

Assuming that once you’ve seen one island, you’ve seen them all. Each has its own vibe, landscape, clientele, food scene, activity choices, price point, and assorted pros and cons. Don’t crowdsource your holiday either, since the cons usually don’t show up in your friends’ Instagram feeds..

Instagram Moment

Right before dinner at Dasheene on St. Lucia (see Meal worth the splurge), stop by the bar for a cocktail while watching the sun set beyond the Pitons; this is the best evening view on the island.

Scam to Avoid

No matter what you’re promised up front—a free dinner, massage, or complimentary nights at some no-name resort—steer clear of timeshare presentations. You may see hawkers at the airports, beaches, or city centers on some islands; don’t waste your precious vacation time engaging with them.

The Souvenir

Many of the islands produce local rum (Chairman’s Reserve and Bounty in St. Lucia, Appleton in Jamaica, Mount Gay in Barbados), but my favorite Caribbean rum treat is the Tortuga-brand rum cake. It’s sold on almost every island, but you’ll find the widest selection of flavors (try key lime if it’s available) at Tortuga’s retail stores in Jamaica and the Bahamas.

Airport Intel

Most Caribbean airports are small, so bring plenty of snacks and entertainment for the kids while you wait for your international flight.

Some countries, such as St. Lucia, require a departure tax payable only in cash (usually either U.S. or local currency). Know your destination’s entry and exit rules, and have enough cash on hand.

Don't Forget to Pack

A pool float. They are so easy to pack and almost impossible to find once you’re in the islands—and while some resorts might have a couple of floats for the pool, most don’t supply them for the ocean. Pack your own inflatable swan or watermelon slice so you can be the envy of the resort when you’re gliding over the waves!


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