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

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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 offers 22 freestanding villa suites), the contemporary, buzzy Le Barthélemy Hotel & Spa, Cheval Blanc St-Barth Isle de France, Eden Rock, Le Sereno and Le Guanahani, which reopened late Fall 2021 as a Rosewood after a multimillion dollar renovation.

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 direct flights from New York only add to the island’s appeal. Also on our radar? The new Rock House from Grace Bay Resorts, located on a 14-acre oceanfront stretch on the north coast of Providenciales, which opened May 2022.

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. And 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 islands 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.

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. Also on our radar: a new Aman resort in development on Canouan Island.

Related: Private Charter Flights: What to Know Now

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.

Related: Harbour Island Insider India Hicks Discusses COVID-19 & More on the Indagare Global Conversations Podcast

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. 

– Elizabeth Harvey on April 6, 2021

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