Think you've seen all the Caribbean has to offer? Some of the least known islands in this diverse archipelago are the most enchanting. Though bound by common threads of crystalline waters, a tropical climate and the laid-back lifestyle, these hidden jewels are as individualistic as they are spectacular.
Contrary to the flash of neighboring St. Barts, Anguilla's mantra is unpretentious luxury. The downy sands near perfection and the waters sparkle with the Caribbean's most vibrant blues. Unlike most of the Caribbean, Anguilla has actively shunned commercialization. Don't expect fast-food chains, cruise ships or casinos here—they're banned. Do expect a sense of community, excellent hospitality and an unspoiled island.
Anguilla's burgeoning restaurant scene has branded the island a foodie destination, but it's still the street eats that are most legendary. On Saturdays, be sure to visit 83-year-old Mable Gumbs' food stand across from the Anguilla National Trust for corn or conch soup, and then head to Ken's Pork for a feast of johnnycakes and grilled meats. Locals earnestly welcome visitors, so it's no surprise to find laid-back nightlife joints such as The Pumphouse, Elvis' Beach Bar, Gwen's Reggae Grill or Bankie Banx's The Dune Preserve filled with a jovial commingling of natives, visitors and expats, which is a rarity on most islands. Locals and tourists also love to converge on Sandy Island, an overgrown sandbar in the middle of the sea that features a colorful restaurant shack and lounge chairs.
The island's newest resort, the Viceroy Anguilla, nestled amid two grand swathes of brilliant beach, offers an exclusive enclave of seductive service and refined modern architecture. Kelly Wearstler's earth-toned interiors are punctuated by the crystal blue waters of the hotel's many private and shared swimming pools, which delicately complement the endless panoramas of sea and sky.
Dominica is the Caribbean's Garden of Eden, a precious tract of Earth teeming with biodiversity and natural phenomena. The island's rugged terrain and lush rainforest harbor more than 1,000 species of flowering plants and 170 bird species, and its coastal waters welcome 20 species of whales and dolphins, including resident populations of sperm whales.
Dramatic waterfalls, emerald pools and breathtaking peaks and valleys dot 300 miles of footpaths through the World Heritage Site Morne Trois Pitons National Park. Deep in the park lies the world's second-largest boiling lake. Dominica's otherworldly Champagne Reef explodes with billions of tiny bubbles from tiny openings in the planet's crust known as fumaroles, which host a variety of seahorses and fish that have adapted to life in these alien conditions.
Immersed in all this natural majesty, the design-savvy Secret Bay eco-retreat takes shape as a series of four elevated glass-and-sustainable-wood tree houses, boasting modern amenities and stylish furnishings. The quartet of eco-masterpieces look out over extraordinary rocky outcrops and aquamarine coves of the island's northwest reaches, best appreciated from the sleek treetop infinity pool.
Along the island's southeastern coastline, at the foothills of the Morne Trois Pitons, Rosalie Bay also subscribes to the eco-luxury mantra. The 28 rooms and suites of the two-year-old resort are found within nine handcrafted, colorful cottages. The bay's beach provides a front row seat for Dominica's wealth of nesting sea turtles and their hatchlings.
Originally christened Oualie (land of beautiful waters) by the Caribs, volcanic Nevis is a history-steeped island that prides itself on tradition and separation from the globalized world. The mountainous terrain is strewn with exquisitely preserved, centuries-old sugar mill plantations and other historic landmarks from Nevis' glory years circa late 1700s. Nowadays, numerous historic relics double as rustic inns. At Golden Rock Inn, a towering 19th-century sugar mill houses a two-story honeymoon suite. At Montpelier Plantation Inn, an 18th-century mill doubles as a private dining experience, while the other original structures house common areas and luxury suites worthy of their Relais & Chateaux pedigree. The powerful and pervasive serenity at the hilltop, ocean-view Montpelier estate is a beacon of escapism, which is why Princess Diana repeatedly visited for a mental respite.
Down on the coastline, the Caribbean's sole Four Seasons resort graces the placid waters of Nevis' Pinney's Beach, where anyone can truly come to understand the island's Carib namesake. With perfectly manicured grounds and framed by the island's glorious apex, the iconic 3,182-foot-high Mount Nevis, Four Seasons Resort Nevis doles out picture-perfect vistas of mountain and sea. A collection of double-story, British-colonial-plantation cottages houses the resort suites and rooms, while private villas dot the property's palm grove. Days here are far from action-packed: You might partake in some paddle boarding, snorkeling or tee time on the Robert Trent Jones II-designed course, but Nevis is all about perfecting the art of unapologetic relaxation, chilling or "limin'," as the locals call it. And there's no better place for limin' than the resort's three pools or next door at the bar, Sunshines, famous for its mind-bending cocktail, The Killer Bee.
Near the northern tip of the Yucatan Peninsula in the Mexican state of Quintana Roo, the tiny island of Holbox is one of the world's last remaining secret hideaways. In recent years, this tropical fishing village with a population of just 1,200, according to the 2005 census, has been hanging up its fishing poles for the tourist trade, capitalizing on snorkeling tours amid the world's largest-known congregation of whale sharks. But even when the graceful, gentle giants aren't feasting on the plankton in the nutrient-rich waters, which typically occurs between May and September, the mile-wide islet resembles a clandestine, sleepy beach town with a bonus of car-free sand roads, native pink flamingos and turquoise waters so rich they've been deemed part of the Yum-Balam Biosphere Reserve.
Given the island's size, it's not too surprising that one hotel has the monopoly on luxury accommodations. Nestled on the western reaches of the island, the 12-room boutique hotel Casa Sandra champions a delightful barefoot sophistication without tarnishing the island's bucolic charm. The exteriors of the whitewashed, palapa-style, thatched-roof hotel showcase iconic Mexican architecture, while bold, hand-embroidered pillows and tapestries from the country's 31 diverse states grace the spacious interiors. Each unit faces the blinding blues of the vast open sea and Holbox's sugarloaf sands. Hotel owner Sandra sought to create an inspirational retreat for artists like her, a place to get carried away with natural majesty and foster creativity, and she has definitely succeeded. So, while unadulterated rest and relaxation might prompt your Holbox sojourn, don't be surprised if your magnum opus soon follows—even if you didn't arrive an artist.
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