Bequia
Why Bequia? Other top Caribbean destinations offer longer beaches, flashier resorts and more productive shopping sprees, but none have the backwater appeal of sweet little Bequia (pronounced beck-way), the first of the Grenadines unfurling south of St. Vincent like the tail on a kite. The six-square-mile outpost is blessed by a spindly shape scalloped with sandy coves and favored yachting harbors. It feels a bit like the Caribbean that yachties might have encountered in the 1960s — catnip to repeat visitors who endure a long haul to get here, but cherish the island’s simple and distinctly uncommercialized ambiance.
Don’t Miss: Sailing is in the blood of Bequians. Embark on a half-day sail by catamaran to visit cave homes at the eerie Moonhole, visit the old whaling station and stop off at one of the island’s white-sand coves for a dip and a rum punch.
The Best Beach: Princess Margaret is the prettiest beach, reached by a brisk one-mile hike over the headland or by dingy from the port. Or a taxi will drop you at less-visited Lower Bay, where ramshackle bars take care of guests with beach chairs, West Indian chicken or goat roti and tree swings.

Dominica
Not to be confused with the Dominican Republic, the Commonwealth of Dominica is the Caribbean’s steepest island — “tall is her body,” the indigenous Caribs called it. It might be the one outpost Columbus would recognize today, still robed magnificently in dozens of shades of green. You’ll trade white-sand beaches for black, and ascend through dense rainforest to smoldering volcanic vistas in Morne Trois Pitons National Park. It’s a World Heritage Site sheltering the region’s richest biodiversity, with mist-shrouded elfin woodlands, bountiful waterfalls, two species of endemic parrots and crater lakes — cold or boiling, take your pick. The natural attractions extend offshore to a rich marine landscape favored by humpbacks and other whales.
Don’t Miss: The swim through evocative Titou Gorge navigates a narrow slot draped in ferns and vines, fed by a waterfall at its end.
The Best Beach: Sand-lovers will want to make the long but highly scenic drive to undeveloped Batibou Beach, on the island’s north end. Caramel sands are fringed in coconut palms, and a beach bar is sometimes manned for libations.

Jost Van Dyke
The British Virgin Islands encompass 50-some idyllic outposts, sliced by the Sir Francis Drake Channel, a fine sailing passage. There are fancier landings, but find me on Jost Van Dyke, a backwater with a population of maybe 300. The number of beach bars: 14 or so. These numbers add up nicely. There is no golf course, no casino, almost no cars — instead, three-square-mile Jost Van Dyke reveals the Caribbean distilled down to its essentials. There’s also no airport, and the usual route from a neighboring island is aboard a dilapidated ferry named When (the appellation makes sense more often than not) or private tours. Dolphins often chase vessels into Great Harbour, where a couple dozen simple structures line the beach on either side of the pier, but you’ll want to set out on foot to explore. At the very least, on an island of bartenders, you can count on the Painkiller — said to have been invented here — to be flawlessly prepared.
Don’t Miss: Foxy’s, the island’s preeminent hangout. The namesake proprietor serenades the crowd most afternoons. We also love the Soggy Dollar Bar, over on White Bay. The Painkiller is the cocktail of choice at both (pineapple juice, cream of coconut, orange juice, rum and — the pinnacle: grated fresh nutmeg on the top). Pair it with a delicious lobster roll.
Best Beach: From Great Harbour, take off your shoes and follow the sand track left over the scrubby hill 1.5 miles to White Bay, a cove of resplendent beauty. White Bay is also home to one of our favorite beach bars/eateries in the Caribbean, the infamous Soggy Dollar Bar, where Painkillers are expertly poured.

Guadeloupe’s Les Saintes
Why Les Saintes? A tiny, less tony take on what St. Barth was like half-a-century ago, this diminutive cluster of islets eight miles off Guadeloupe offers a full-on dose of French charm spiced with hard-scrabble fishermen. Terre-de-Haut, the main island, is perfectly sized for a day trip, and the port town is chockfull of options for accras de morue (fish fritters), ice cream and beer. Gaze up from the port and you’ll spot Fort Napoléon sitting atop the hill overlooking the harbor. Locals call it the Gibraltar of the Caribbean, which is a bit of an exaggeration, but it is large enough to have never seen a major battle, and the museum is worth a gander; the view spills for miles in all directions. Shopping won’t weigh you down, but save room for a local find: delicious punch coco, sold out the back door of many island homes in unlabeled bottles.
Don’t Miss: On arrival near the pier, women in colorful madras fabrics sell tourment d’amour — the agony of love — from wicker baskets. The salty-sweet coconut tarts are a specialty of the island, sold by the bagful.
Best Beach: It’s a one-mile walk or short taxi ride along a quiet country road from the port to Plage de Pompierre, which has bathrooms and picnic tables, but is otherwise blissfully undeveloped. On the opposite end of the island, Anse Crawen is a remote cove for those who like their sunbathing in the altogether.

Montserrat
Why Montserrat? In its glorious heyday, Elton John and Paul McCartney once recorded albums here, but most of us are more familiar with a more recent tragedy: In 1995 volcanic Soufriere Hills awoke after 300 years of slumber, burying the island’s (evacuated) capital of Plymouth. The Emerald Isle, as it was once called, is now the Volcano Isle, and Montserrat is slowly rebuilding. Although no new lava has been coughed up for more than a decade now, the southern two-thirds of the island remains an “exclusion zone” — suitable only for supervised day tours and providing a fascinating glimpse into Mother Nature’s kitchen. The northern third is inhabited by roughly 5,000 residents, and sideshows of birdwatching, diving and hiking have made a rebound.
Don’t Miss: The ash-laden volcano is a commanding sight, and the ruin of the former capital is like a Caribbean Pompeii. The best accessible view is offered from the Montserrat Volcano Observatory, where the volcano panorama is accompanied by scientist-led tours of the monitoring effort.
Best Beach: From the port at Little Bay it’s a one-mile hike over the headland to Rendezvous Bay, the island’s one gold-sand beach. It’s undeveloped, and you might have it all to yourself. You can also hire a dingy to take you over.