Indagare Caribbean Islands Matchmaker: The Best Caribbean Islands Open Now 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. All of these destinations are open to U.S. passport holders now, although some currently require American travelers to stay put upon arrival. On these islands though, accommodations are so dreamy that we wouldn’t mind a few days of quarantine, be it in a a private villa with beach access, a yacht charter with all the creature comforts or a hotel with enhanced sanitization and thoughtful social-distancing procedures. Plus, the days of sunshine and 80-degree temperatures seen in the late fall and winter months mean that outdoor dining, golfing, snorkeling and many other adventure activities will be in full swing on-property. 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 coronavirus travel safety, COVID-19 hotel policies, transportation options, private villas and charters and more. For further inspiration, explore our curated list of Indagare’s favorite destinations open to U.S. passport holders now: Coronavirus Travel Information: What’s Open To Americans.

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, opening at The Christopher October 15. 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 (reopening October 20), Eden Rock, Le Sereno and Le Guanahani, opening this month as a Rosewood after a multimillion dollar renovation.

Entry Requirements: Non-vaccinated travelers are prohibited. Fully vaccinated travelers must show proof of a negative PCR test from within 72 hours before their departure or a rapid antigen test within 48 hours of their departure (see full entry requirements).

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 resort, located on a 14-acre oceanfront stretch on the north coast of Providenciales, coming soon from Grace Bay Resorts.

Entry Requirements: Only fully vaccinated travelers will be allowed entry into Turks & Caicos. Visitors must acquire Travel Authorization and show proof of a negative test result from within three days of arrival, as well as travel insurance (see full entry requirements).

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. This year, Lovango Resort & Beach Club has opened on a private cay in between St. Thomas and St. John. 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 will 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.

Entry Requirements: Vaccinated travelers may provide proof of full vaccination. Unvaccinated travelers must complete a test within five days prior to travel (see full entry requirements).

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.

Entry Requirements: All American travelers must complete a RT-PCR test within 72 hours before arrival and must be retested upon arrival. Vaccinated travelers must quarantine for 48 hours while awaiting test results. Unvaccinated travelers must quarantine for 14 days and be retested between days four and seven (see full entry requirements).

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 the 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 charming, oceanfront cottages at The Dunmore which also has one of the best restaurants on island. We also love Bahama House, and 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.

Entry Requirements: Vaccinated travelers must fill out an online health form with proof of vaccination and show proof of negative results from a rapid or PCR (molecular swab) test. Unvaccinated travelers must present a PCR test with a negative result in order to apply for the same form (see full entry requirements).

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.

Entry Requirements: All travelers, regardless of vaccination status, must apply online for a BVI Gateway Travel Authorization Certificate ($35 per person if vaccinated; $175 if unvaccinated). Upon arrival, vaccinated travelers must provide proof of a negative Covid PCR test result taken within five days of arrival. Unvaccinated travelers will undergo a second RT-PCR COVID-19 test upon arrival, followed by a seven-day quarantine period and a third Covid test on Day 7 (see full entry requirements).

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

A thousand miles north of the Caribbean Sea. And yet, depending on the season, this Atlantic Island 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, with top hotels including stylish The Loren at Pink Beach and the fresh and modernized Rosewood Bermuda.

Entry Requirements: Travelers must provide proof of negative results from a PCR test taken within seven days of departure and pre-apply for a travel authorization one to three days prior to departure. Upon arrival, vaccinated travelers must take a second PCR test and quarantine while awaiting results. Unvaccinated travelers must quarantine immediately for 14 days at a government-approved quarantine hotel and take their second PCR test on the fourth day after arrival. Upon receiving a negative result, they can complete the remainder of their 14-day quarantine at a hotel of their choosing (see full entry requirements).

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 coronavirus travel safety, COVID-19 hotel policies, transportation options, private villas and charters and more. For further inspiration, explore our curated list of Indagare’s favorite destinations open to U.S. passport holders now: Coronavirus Travel Information: What’s Open To Americans.

Global entry requirements and COVID-19 safety policies are subject to change at any time, and the information detailed here may not be reflective of these changes. For the most up-to-date information regarding your current and future travels, please consult the U.S. State Department and CDC websites directly.

– Elizabeth Harvey on October 14, 2021


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