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: Fully vaccinated travelers may enter with proof of full vaccination (two doses of Pfizer, Moderna or AstraZeneca or one dose of Johnson & Johnson) from at least two weeks prior to arrival. All other 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: No test is required for fully vaccinated travelers. If partially vaccinated or unvaccinated, travelers must complete a RT-PCR 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 (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 a negative rapid or PCR test. Unvaccinated travelers must present a PCR test with a negative result in order to apply for the same form. All travelers must show proof of negative results from a rapid or PCR (molecular swab) test from no more than three days before arrival (see full entry requirements).
Only 16 miles long and three miles wide, Anguilla has long been a favorite of laid-back sophisticates looking for a sun-soaked escape. Known for lovely long beaches and fantastic local restaurants, the tiny island offers more than 30 quiet stretches of sugary sand, as well as some of the best food in the Caribbean. This allows guests of Anguilla’s top properties the option of venturing comfortably off-property for meals or staying back to enjoy the likes of Pimms’ Moroccan influenced Caribbean fare at the classic Belmond Cap Juluca or the variable cuisine at any of the full-service Four Seasons Anguilla’s six restaurants. A safe island with plenty to explore, Anguilla is also an ideal destination for renting a private villa should you prefer more privacy and room to roam.
Entry Requirements: Non-vaccinated travelers cannot enter Anguilla. Fully vaccinated travelers (as well as unvaccinated children under 18 and unvaccinated women who are pregnant, who are exempt from the vaccination requirement) must submit a PCR test (within 72 hours before entry) or Rapid Antigen (within 48 hours before entry). Anguilla also conducts tests upon arrival; however, if your last does was within 6 months prior to entry you will not be tested upon arrival (see full entry requirements).
Related: Indagare’s Anguilla Matchmaker
Best Caribbean Island for Soul and Island Spirit: Jamaica
Instead of an island overrun by tourism, Jamaica is an island defined by its natural, undeveloped beauty and its people, who celebrate life––often through the reggae music the island is famous for. Those looking for a cool and idyllic luxury retreat will find their base at GoldenEye, the incomparable James Bond hideaway surrounded by caves and lagoons that was the former refuge of Bond author, Ian Fleming. Meanwhile, on the western side of the island, Round Hill Hotel and Villa merges the exclusivity of an old school New England country club with the warm hospitality of the tropics in its airy seafront rooms and villas.
Entry Requirements: All travelers must show proof of a negative test within three days before entering the country and have an approved Travel Authorization form (see full entry requirements).
Best Caribbean Island for an On-Property Adventure: Dominican Republic
Sprawled beneath tall coconut palm trees, the Dominican Republic’s top resorts offer travelers a chance to flop-and-drop at one luxe property, where a wealth of athletic, leisure and cultural pursuits can all be enjoyed on site. Properties like Casa de Campo and Eden Roc at Cap Cana offer plenty of classic activities, including golf, tennis, water sports, horseback riding, boat charters, fishing and kids’ clubs—but the uniquely Spanish flavor of the Dominican Republic’s culture can also be experienced through merengue lessons, rum tasting, cigar making demonstrations and more. Couples should consider Amanera, an intimate jungle oasis that combines comprehensive amenities and excursions with the sleek style and serenity of the Aman brand.
Entry Requirements: No test results required (see full entry requirements).
Related: Direct Flights to the Caribbean
Best Caribbean Island for Five-Star Family Fun: Antigua and Saint Kitts and Nevis
Easily accessed via direct flights from the U.S. and Europe, Antigua promises both leisure and adventure for travelers of all ages. Families flock to Oetker Collection’s upscale, all-inclusive Jumby Bay offering a private island location with secluded villas, a friendly atmosphere and top-notch beachfront amenities, while Antigua’s first luxury hotel, Curtain Bluff guarantees personalized service and a host of activities (including squash, waterskiing, snorkeling, kayaking, tennis and more) that are well-suited to families with older children.
Entry Requirements: Fully vaccinated travelers must present proof of full vaccination. Unvaccinated travelers between the ages of five and eighteen must present a negative Rapid Antigen within four days prior to entry. All other unvaccinated or partially vaccinated travelers are not permitted entry (see full entry requirements).
Related: Where to Go for the Holidays—And What to Know Before You Go
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 perfect 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.
Entry Requirements: Only fully vaccinated travelers will be allowed entry into St. Kitts & Nevis. Travelers must submit a negative Rapid Antigen test from within one day before arrival or a RT-PCR taken within three days before arrival (see full entry requirements).
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.
Entry Requirements: All travelers must show proof of a PCR test within three days prior to arrival or Rapid Antigen test within one day prior to arrival (see full entry requirements).
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.
Entry Requirements: No test is required for vaccinated travelers. Unvaccinated travelers must present a PCR test done within five days before arrival (see full entry requirements).
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 charms with 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, on a three-mile stretch of sandy paradise with lush gardens overflowing with coconut palms and pineapple trees (with a mesmerizing soundtrack of chirping coqui frogs). In addition to the guest rooms and suites that 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.
Entry Requirements: Domestic travelers are not required to present proof of vaccination or a negative test (see full entry requirements).
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.
Entry Requirements: Fully vaccinated travelers must show proof of vaccination and a negative test within 48 hours prior to arrival to be exempt from entry testing and portal requirements. Partially and unvaccinated travelers must apply online for a BVI Gateway Travel Authorization Certificate ($175 ), show proof of a negative test three to five days before arrival, show proof of travel insurance and quarantine upon arrival (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: All travelers need an approved Travel Authorization ($40). Fully vaccinated travelers must present a PCR test from within four days prior to arrival or an antigen test from within two days prior to arrival. Unvaccinated travelers 12 and up are not permitted to enter (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.
