Indagare Caribbean Islands Matchmaker: The Best Caribbean Islands for Every Traveler

The Caribbean has long drawn couples, families and friends for easy warm-weather getaways, thanks to its powdery white-sand beaches, warm turquoise waters and pampering resorts—but every island has its own atmosphere and specialties, and choosing the right one can be challenging. Here, we outline Indagare’s favorite Caribbean islands for every type of traveler. Read on to discover your Caribbean escape!

Contact Indagare or email your trip designer for assistance planning a Caribbean vacation. Our team can match you with the accommodations and activities that are right for you and provide information on transportation options, private villas and charters and more. 

Best Caribbean Island for a Jet-Set Scene: St. Barth’s

St. Barth’s has managed to maintain its native gems—expansive beaches, beautiful hiking trails, natural pools and more—while consistently satisfying stylish globetrotters with its world-class resorts and some of the Caribbean’s top shopping and dining. Enjoy festive beachfront lounges and swanky restaurants, including the new South-of-France-inspired restaurant Rivyera, created by Chef Arnaud Faye, at The Christopher, which opened Fall 2021. Jet-setters can stay at legendary properties like Le Toiny (which has 22 freestanding villa suites), the contemporary, buzzy Le Barthélemy Hotel & Spa, Cheval Blanc St-Barth Isle de France, Eden Rock, Le Sereno and Rosewood Le Guanahani.

Related: Indagare’s St. Barth’s Matchmaker

Best Caribbean Islands for a Chic Romantic Getaway: Turks and Caicos

The top resorts on Turks & Caicos promise the ultimate secluded romance: Couples can retreat into the exclusive villas at COMO Parrot Cay or the private pavilions at the sleek and serene Amanyara (all of which are located around ponds, along the beach or atop volcanic rock ledges overlooking the ocean), while Grace Bay Club offers separate accommodations and pools to keep both couples and families happy. The latest spot on our radar is Beach Enclave, a new-to-us villa option where industry leaders gathered in August 2023 to discuss what’s next in the evolution of luxury travel. And those looking for a low-key, secluded retreat should consider Pine Cay. The direct flights from New York only add to the island’s appeal.

Related: Indagare’s Turks and Caicos Matchmaker

Best Caribbean Islands for a Convenient Hideaway: U.S. Virgin Islands

About 1,000 miles southeast of Miami, the U.S. Virgin Islands are perfect for a convenient Caribbean getaway. The three major islands—St. Croix, St. John and St. Thomas—are known for their charming pastel buildings, crystal-clear harbors and rich cultural diversity. From 18th-century sugar mill tours to paddle-boarding and hiking to turtle nesting grounds on white-sand beaches, the U.S. Virgin Islands offer activities for all ages and interests. In early 2021, Lovango Resort & Beach Club opened on a private cay in between St. Thomas and St. John, the first new build on the island

s in 30 years. From the owners of the Nantucket Hotel and Winnetu on Martha’s Vineyard, Lovango has a mix of villas, luxe treehouses and glamping tents (with environmentally friendly air conditioning and private bathrooms). Guests have prime access to the island’s beach club—which has already become a destination for the yacht set—as well as to the sands and hiking trails of Virgin Islands National Park in Saint John, a short boat ride away.

Related: Best Winter Vacation Ideas for 2024: 24 Trip Ideas from Antigua to Zimbabwe

Best Caribbean Islands for a Quiet, Private Retreat: Canouan Island and Mustique

Two of the Caribbean’s best-kept secrets, Mustique and Canouan Island are both home to spectacular powder-white sand, glowing turquoise waters and lush, mountainous landscapes. These relatively untouched enclaves are extraordinary places to disconnect amid natural splendor. Mustique is one of those rare destinations that was created by one visionary and lives up to its legendary hype, with a host of wonderful private villas on offer, in addition to the iconic Cotton House hotel. Meanwhile, the pint-sized gem that is Canouan Island is truly quiet and is best enjoyed from the contemporary and elegant Mandarin Oriental.

Best Caribbean Islands for a Low-Key Escape: Harbour Island and Anguilla

Harbour Island is a tiny Bahamian island (known as “Briland” to both vacationers and locals) that allows laidback beach bums to luxuriate in simple pleasures: homemade croissants at Arthur’s, shopping at Blue Rooster and Sugar Mill, a festive lunch at Sip Sip and strolling the east coast’s pink-sand beach. What the hotels lack in five-star trappings, the island—lined with pastel British-colonial cottages wrapped in bougainvillea—makes up for with its chic yet easygoing vibe and charming sense of place. Harbour Island is also a great spot for teens who will love exploring by golf cart. The best of Harbour Island can be found in the oceanfront cottages at The Dunmore, which also has one of the best restaurants on island. We also love Bahama House, an Indagare Index resort from Eleven Experience. Outside of Harbour Island, other top Indagare picks in the Bahamas include the Ocean Club, a Four Seasons Resort, and Rosewood Baha Mar, both in Nassau.

Four Seasons Nevis, Courtesy Christian Horan

Four Seasons Nevis, courtesy Christian Horan

Relaxation and a laid-back atmosphere meet the opportunity for constant entertainment and adventure on Saint Kitts and Nevis. Set on four miles of beach, the Four Seasons Nevis is the ultimate base for activity, with abundant hiking and water activities as well as access to the resort’s 10 tennis courts, 18-hole golf course, three infinity pools and an excellent kids club. For families looking for more relaxation in their island adventure, the Park Hyatt St. Kitts is the ideal place to combine lazy days by the pool with on-property kayaking and snorkeling. The great food options from their three on-site restaurants mean you won’t have to leave the resort at all if you don’t want to.

Related: Indagare’s Top Hotel Picks for Kids Under 10

Best Caribbean Island for an Elegant Escape: Barbados

A tropical getaway with equal emphasis placed on its British heritage and world-class luxury, Barbados marries the relaxed vibe of the islands with the mannered charms of England. Traditions such as polo matches, horse races and estate tours provide travelers with ample diversions, while properties like Sandy Lane, a former playground for British royalty, maintain a slightly formal air with lavish accommodations, fine dining and a glamorous clientele.

Related: Indagare’s Barbados Matchmaker

Best Caribbean Island for Culture and Beach: St. Lucia

For an enchanting Caribbean getaway that is accessible but feels culture-rich and far-flung, St. Lucia weaves a tapestry of African, Indian and Creole influences that is as lush and varied as its fabled rainforest. With pampering luxury resorts—including Sugar Beach, A Viceroy Resort and Jade Mountain—and a dramatic, mountainous terrain, plus world-class diving and a vibrant arts scene, St. Lucia promises to satisfy the travel-starved who are looking for a beach retreat with a bit more soul.

Related: Easy Beach Getaways

Best Caribbean Island for a Quick Trip Close to Home: Puerto Rico

Just a four-hour direct flight from New York and a two-and-a-half-hour direct flight from Miami, Puerto Rico has a vibrant blend of cultures, as well as white-sand beaches and tropical rainforests ripe with adventure. One of the best resorts on the island is the Ritz Carlton Reserve at Dorado Beach, set on a three-mile stretch of sandy paradise with lush gardens overflowing with coconut palms and pineapple trees (and a mesmerizing soundtrack of chirping coqui frogs). In addition to the guest rooms and suites spread across 11 two-story buildings, the property has two-, three-, four- and five-bedroom private residences, available for weekly rentals and ideal for families traveling with kids or those looking for a higher level of privacy and space.

Best Caribbean Island for the Ultimate Property Takeover: Necker Island and Moskito Island, the British Virgin Islands

No one does a luxury island hideaway quite like Richard Branson. His Virgin Limited Edition property on Necker Island, with its wraparound terraces, excellent chef-prepared seafood and every toy imaginable­­—catamarans, infinity pools, tennis courts and rooftop hot tubs to name a few—is over-the-top luxury at its finest. The island is a wonder in itself, home to wildlife like flamingos and endangered ring-tailed lemurs, plus grottoes and white sand beaches. And Necker Island is no longer your only takeover option in the British Virgin Isles: On nearby Moskito Island, within view of Necker, Branson has opened two new estates in addition to his own private compound. The Oasis Estate and the Point Estate each come with private chefs and a wealth of activities to complement their panoramic views and sleek designs.

Honorable Mention: Best Non-Caribbean Island for a Classic Caribbean Holiday: Bermuda

This Atlantic Island is located a thousand miles north of the Caribbean Sea, and yet, depending on the season, Bermuda can offer a Caribbean-esque getaway (colonial architecture, pink-sand beaches and crystal blue waters) within a couple hours by plane from New York and Boston. Great Britain’s oldest existing colony still feels traditionally English, but its proximity to the U.S. means there is a strong American influence. Note that while most Caribbean getaways have their peak season in the winter, Bermuda is a summer destination, with golf, sailing, balmy beach days and other activities all on offer. Top hotels include stylish The Loren at Pink Beach and the fresh and modernized Rosewood Bermuda.

Contact Indagare or email your trip designer for assistance planning a Caribbean vacation. Our team can match you with the accommodations and activities that are right for you and provide information on transportation options, private villas and charters and more. 

Plus: Travel in style with our exclusive beach shopping edit from our partner Mytheresa.

– Elizabeth Harvey on October 14, 2023


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