Setting off for the Caribbean seems so easy—until you have to choose from among 25 countries and an untold number of resorts. And then there’s what to do about the kids or the sand-averse spouse. Which is why we’ve broken down 16 of the most in-demand destinations by need. Beach haters, sun bunnies, food snobs: there is an island for you, whoever you are.

Cheval Blanc St. Barth
Credit: Frederic Lagrange

I Don't Want to See a Ton of Americans.

St. Bart’s is filled with fancy Frenchmen, Brits, and Italians seeking R&R and the scene. But the eight-square-mile island also has an unassuming (and relatively inexpensive) side, too. Four places to hole up, on either end of the budget.

$: Emeraude Plage Hotel is a cluster of 28 bungalows and suites on the glamorous Baie de St. Jean, a sheltered beach scattered with boutiques and restaurants. Minimalist interiors and wooden seafront decks serve to lower your pulse.; doubles from $350.

Simple but chic, Salines Garden has five cottages with four-poster beds and private patios, as well as a pool, all close to wide Anse de Grande Saline beach.; doubles from $120.

$$$$: In November, hillside Le Toiny emerged from a face-lift by English interior designer Bee Osborn. Its 15 villas now have bleached-wood floors, and there’s a new beach club carved from two 18th-century cottages.; doubles from $730.

A posh 40-room hideaway run by LVMH, Cheval Blanc St.-Barth Isle de France is set on Baie des Flamands—with arguably the island’s best beach. Order rosé and burgers for lunch at the decadent open-air restaurant.; doubles from $640.

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Cuba was Travel + Leisure’s destination of the year in 2015, but the hype isn’t over yet. President Obama’s historic visit in March, which marked the first time a U.S. president walked on Cuban soil in 88 years, was just a prelude for all that’s to come for this once closed-off Caribbean isle. Direct service by major carriers including JetBlue and cruise lines like Carnival are opening up the country more than ever before, and signs of the times have already begun to creep in, from innovative new hangouts like art bar La Fábrica to a swath of hotel openings including Pullman Cayo Coco. June marks the beginning of hurricane season in the Caribbean, but Cuba is often less affected than other islands. Think languid summer days, occasional thunderstorms, and seriously low season fares—all the ingredients for a jaunt to frenetic, colonial Havana, with its ceaseless salsa and ’57 Chevys trundling down cobbled streets. Mark Williamson/Getty Images

I Want to Time-Travel.

From the moment you leave the airport or port in a classic car, a trip to Cuba is a step back to the 1950s. Havana’s the highlight, with its grand buildings, privately owned restaurants, and Hemingway haunts like El Floridita. But on the southern shore, Santiago de Cuba’s cultural history and Cienfuegos’s French elegance are just as enthralling. The best way to see it: Rooms at even the swankiest hotels—like the Nacional or the Saratoga—could use some love. Sleep instead in the comfortable confines of the Adonia, the flagship of Fathom cruise line (from $1,800 per person, with meals and activities), which makes a seven-day trip from Miami.

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Courtesy of Hermitage Bay

I Don't Want to Go Off-Property.

In Antigua, which pretty much invented the exclusive all-inclusive, each of these three resorts has fewer than 75 rooms—and as many as 216 employees—meaning everyone gets VIP treatment. Read more.

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I Want it All—By Lunch.

Turks and Caicos is one of the most accessible destinations, popular with travel editors and celebrities alike. Some picks for those who want to hit the beach as quickly as possible....

Less than 3.5 hours from JFK to beach:

Grace Bay Club: Get on the earliest JetBlue flight, and by noon you can be dozing on a voile-swathed daybed on the beach while a waiter brings more champagne and jerk-spiced corn on the cob. This 82-room resort has a glamorous vibe and an infinity pool framed by palm trees.; doubles from $640.

Less than 4 hours from JFK to beach:

Amanyara: This quiet resort on a remote corner of the island has 56 wide-eaved pavilions and villas with glass sliding doors abutted by ponds, patios, or the half-mile-long beach. Such Zen minimalism is as calming as you’d expect: the only evening noises are the cooing of the birds.; doubles from $1,450.

More than 4.5 hours from JFK to beach:

Parrot Cay: The extra hour gets you to a 61-room private-island resort that’s beloved by A-listers like Donna Karan. Why? The obvious white-sand beaches and turquoise waters, plus a yoga-centric spa and some of the best (and healthiest) food in the Caribbean.; doubles from $880.

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Brian Pineda

I Don't Want to Leave the U.S.

Puerto Rico is easily the Caribbean’s most convenient destination (JetBlue offers multiple flights a day from New York City). San Juan’s Old Town is always good for a stroll, but there’s more elsewhere, like these six highlights. Read more.

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I want to leave my kids at camp and have a much-needed cocktail.

It’s rare to find a resort that’s truly enjoyable for the whole family, but the Ritz-Carlton, Grand Cayman (doubles from $799) delivers. As you spa at La Prairie, golf, and engage in adult conversation over grilled wahoo with bok choy and green papaya by chef Eric Ripert at Blue, you’ll be comforted by the knowledge that your kids are having tons of fun participating in outdoor edutainment. Through the resort’s Jean-Michel Cousteau Ambassadors of the Environment program, off-spring can visit with blue iguanas, make their own pizza and pasta with chefs at the Andiamo restaurant, and snorkel with marine experts to learn what’s going on with the coral, sponges, and thousands of fish under the sea.

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As If I'd Go Anywhere Without My Golf Clubs.

The Dominican Republic has 26 golf courses to its name, but the big news this year is that the storied course Playa Grande—known as the Caribbean’s Pebble Beach, on the country’s northern coast—has just been renovated. Check in to the new, supremely stylish nine-bungalow Playa Grande Beach Club (doubles from $800) nearby; celebrated interior decorator Celerie Kemble collaborated with preservationist Elric Endersby on the design.

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Courtesy of Sunsail

Forget Resorts. I'd Rather Sleep on a Yacht.

The British Virgin Islands, a smattering of four main islands plus dozens of smaller ones, are perhaps best seen by yacht. This type of travel combines the privacy of a villa with the mobility of a cruise. Charter a boat with Sunsail (seven nights from $2,040 for a two-cabin yacht), and here’s what your week might look like. Read more.

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I Want to Gain 10 Pounds.*

On Barbados, a mash-up of cricket-loving Brits, epic surf, and gifted cooks has created one of the region’s best food destinations. These are the three things you need to eat.

Fish Cutter at Cuz's Fish Stand: The simple, addictive sandwich ($7.50) of pan-fried fish, lettuce, and tomato— topped with an optional slice of cheddar or a fried egg— draws lines of devotees including chef Marcus Samuelsson to this simple lean-to in Bridgetown.

Grilled Lobster at the Fish Pot: In an 18th-century fort, this is the place for lobster ($49) that’s so fresh it puts all other versions to shame. The restaurant is part of Little Good Harbour, a serene resort composed of seaside cottages with 21 suites. littlegoodharbourbarbados. com; doubles from $299.

Flying Fish at the Oistins Fish Fry: A Bajan specialty, flying fish is a mild white catch that’s breaded, fried, and served with plantains and rice ($12.50) at this Friday-night party in the southwestern town of Oistins. Wash it down with Banks beer, the refreshing local lager.

*Wait—I Want to Lose 10 Pounds: Skip Barbados and spend a week at the BodyHoliday, an all-inclusive St. Lucia resort that offers spinning, Pilates, yoga, tennis, and spa treatments—plus dairy-free, gluten-free, nut-free meals.; from $700 per person per night.

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© Chris Fredriksson / Alamy Stock Photo

Hipster Sports are my Jam.

Aruba is the place to burn off excess energy, whatever you’re into (even, heaven forbid, stand-up-paddleboard yoga). Read more.

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Hello? Where's the Culture?

Chris Blackwell, founder of Island Records and the GoldenEye resort (doubles from $400)—which debuted 26 new beach huts this winter—on what to do in Jamaica:

“Instead of bars or clubs, many people in Jamaica go to sound-system dances. Held on lawns or in the street on Friday and Saturday nights, they’re DJ-led parties that are always memorable—the dancing is truly wild. It’s rude, it’s fun, it’s outlandish, and it’s to a mix of reggae, dance-hall music, and occasional classic R&B. You’ll only find out about sound-system dances through Jamaicans, and you should have a local accompany you: we have three or four staff members who’ll take guests and help them enjoy the evening out.”

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Getty Images/iStockphoto

My Tweens are Dying to Slide Down the Mayan Temple.

Once the Bahamas’ one-square-mile Atlantis (doubles from $310) has captured your kids’ attention, just give in. Here’s what a day could involve.

8 a.m. : Upon waking at the Cove, they’ll realize it’s not so bad sharing with siblings since every newly renovated suite has a spacious living room. Plus, the bathroom’s big enough to comfortably lock themselves into when everyone’s being so unfair.

9 a.m. : In Aquaventure, the water park: one waterslide down...17 to go, including the trip-defining Leap of Faith, which drops 60 feet down the side of a faux Mayan temple, propelling them into a clear tube that snakes its way through a shark-filled lagoon.

12 p.m. : Hunger necessitates a hastily gobbled lunch. They breathlessly regale you with slide stories over hamburgers and root-beer floats at Johnny Rockets. Sandwiches $6–$11.

2 p.m. : Meal digested, they’re off to get wet-suited at 14-acre Dolphin Cay to swim with a chirpy dolphin. They’ve never been this polite, asking you to please Snapchat the moment they rise above the water with the dolphins’ cool, smooth noses nudging their feet.; from $199.

6 p.m. : They proclaim the pasta bolognese at Olives the best they’ve ever eaten, while making numerous repulsed faces at your own choice, oysters. Entrées $14–$56.

8 p.m. : Final energy reserves are expended at Club Rush, the “club” for 9- to 12-year-olds, where they master PlayStation and request Taylor Swift on repeat on the dance floor.

9 p.m. : Drifting off to sleep, they dream of doing it all again tomorrow.

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Courtesy of Malliouhana

I Need My Vacation to Be Art-Directed.

The approximately Manhattan-size island of Anguilla didn’t have electricity or running water until the 1980s. Today it straddles the line between sleepy and sumptuous, with truly unspoiled beaches where the palm trees are tilted just so and hotels strike a variety of style notes.

Vaguely New Age: Opened this month as the first upscale property on Anguilla’s east end, the white-and-teak, pavilion-style Zemi Beach House sits on beachfront limestone bedrock edging the bar-speckled Shoal Bay. There are five restaurants and bars for 70 rooms (you do the math), plus a 15,000-square-foot spa specializing in herbal and mud-based treatments.; doubles from $699.

Discreetly Retro: With a pleasantly 1980s vibe in its cluster of Moroccan-inspired buildings on a mile-long, crescent-shaped beach, Cap Juluca is old-school in its sensibilities: because it’s neither splashy nor sceney, it’s the favorite of private types like Jennifer Aniston. Every room is on the beach, where the loungers are spaced out for maximum privacy.; doubles from $995.

Sunny and Family-Friendly: Malliouhana (shown above) opened in 1984, but its rooms—set on 25 acres between a sugar-sand beach and tropical trees—were redone in 2014 in a perfectly preppy color palette of white, mango, and mint. Don’t miss lounging by the new infinity pool.; doubles from $975.

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Courtesy of Jade Mountain

I Want to Instagram By the Pool.

St. Lucia and its raft of lavish hotels will have you itching for your iPhone.

#pitons: Sexy Jade Mountain has the best views of the island’s iconic twin peaks, and 24 of its 29 rooms have private pools.; doubles from $1,080.

#cottageliving: Every one of Viceroy Sugar Beach’s whitewashed, cottage-style quarters has a private pool.; doubles from $425.

#seclusion: Sophisticated and away from the action, Cap Maison oceanview villas all have private pools.; doubles from $440.

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Wait...I Hate Beaches!

St. Kitts might be best known for its white, gray, and black sandy shores, but you can leave them in the dust and make haste to Belle Mont Farm in Kittitian Hill, a resort amid the farmland, fruit groves, and forests on the northern edge of the island. As if the bucolic vistas and pastel rooms weren’t enough, the property has an organic farm that grows more than 100 different types of mango alone. You can bombard the horticulturist with questions about why your own daisies won’t grow, and you can forage for the lemongrass, sour oranges, bay leaves, eucalyptus, rosemary, cinnamon, and ginger that will make its way into dinner at the restaurant—and treatments at the new spa. And in case you change your mind about the whole beach thing, the concierge will shuttle you to a swath of sand 10 minutes away.; doubles from $700.

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