Make Your Next Trip Extraordinary

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

by | August 13, 2018

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

Trusted Travel Expert
Lindsey Epperly Sulek

When you’re seeking a Caribbean getaway to a 5-star resort, a top boutique hotel, or a luxe all-inclusive, Lindsey can match you to the right island and property—whether you want a nonstop flight and a modern aesthetic, or you are game for a puddle-jumper to reach a far-flung island with an “Old Caribbean” feel. She favors those properties where she can procure upgrades, meal credits, and other perks for her travelers, and where she can ensure first-rate service. Most of Lindsey’s travelers want to spend their vacation relaxing on the beach; for those wishing to sprinkle in a few island or water-based excursions, she’ll work with your resort’s concierge to choose the best local outfitter and ensure that everything runs smoothly. When Lindsey’s not available, travelers speak with her husband and business partner Jeremy, a self-described beach bum at heart with many a favorite toes-in-the-sand island hangout to recommend.

Trips have a 3-night minimum and start at $600 per day for two travelers. Lindsey charges an additional trip-planning fee of $350.

Covid safety intel

While government rules vary from island to island, masks are mandated on most, particularly in common areas of resorts. Lindsey works with hotels, villas, drivers, and activity and excursion providers that have adopted strict safety protocols; it helps that so much of Caribbean life happens outdoors. She’s steering travelers toward resorts with standalone cottages, such as Sugar Beach in St. Lucia, where every bungalow and villa comes with its own private plunge pool. And she recommends restaurants that are open-air and space tables comfortably far apart—da Conch Shack on Turks & Caicos, for instance. Depending on the airport, Lindsey can sometimes expedite your arrival and departure so that interactions with others are minimized.

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 Island Resort 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 Lindsey get a $100 spa credit per room, plus upgrades, early check-in, and late checkout when available.

Jumby Bay Antigua

Jumby Bay Island Resort Antigua. Photo: Lindsey Epperly

What to Eat

Restaurants 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.

Contact Lindsey

Not sure if this is the right person for you? Ask Wendy

Best Time 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 Time 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 the best 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!


So incredibly easy...

Deborah Wente | August 31, 2021

We were disappointed...

Y. H. | July 16, 2021

It really is such a refreshing…

John Arndt | July 8, 2021
  • Did you use The WOW List to plan a trip with this Trusted Travel Expert?

    If you’ve returned from a trip arranged via Wendy’s WOW system, please leave a review of your experience so your fellow travelers can decide whether this trip planner is right for them. Include your name (because anonymous reviews are not fair), the month/year of your trip, the destination(s) you traveled to, and your advice for anyone who is considering using this trip designer.  If you’d prefer to share your review privately, email Wendy