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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 for you can be challenging. Here, we outline our favorite Caribbean islands that are open now for American passport holders—and explain which one is right for every type of traveler. Although some of these destinations do require that American travelers stay put upon arrival, the accommodations on offer are so dreamy that you’ll be more than happy to quarantine, whether you opt for a private villa with beach access, a yacht charter with all the creature comforts or a hotel that is practicing 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, destinations that are open to travel, 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, with swanky hilltop restaurants and festive beachfront lounges abounding. Jet-setters can stay at such legendary properties as Le Toiny (which offers 14 freestanding villa suites and a 72-hour cancellation policy), the contemporary, buzzy Le Barthélemy Hotel & Spa (reopening October 28), Cheval Blanc St-Barth Isle de France (reopening October 29), Eden Rock (reopening October 22) and Le SerenoAlso on our radar? The October 15 opening of Hôtel Barrière Le Carl Gustaf, which offers a highly private experience with Michelin-starred dining, 23 rooms (with 13 freestanding cottages) and a prime location in Gustavia.

Entry Requirements & COVID-19 Safety: As of October 14, St. Barth’s is open to U.S. citizens. All travelers must provide proof of negative results from a COVID-19 RT-PCR (real-time polymerase chain reaction) test taken 72 hours before their departure flight. Travelers must also present a sworn statement that they have no symptoms and have not knowingly been in contact with a confirmed case of COVID-19 in the 14 days before the flight. U.S. citizens are not required to quarantine but may be subject to health screening upon arrival. For travelers staying for more than seven days, a second COVID-19 RT-PCR test is required on Day Seven or Eight of the stay (the cost is 135 euros and the test center is in Gustavia) (source: U.S. Embassy in Barbados, the Eastern Caribbean, and the OECS Website).

Related: Indagare’s St. Barth’s Matchmaker

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

The top resorts on Turks & Caicos promise the ultimate in secluded romance: Couples can retreat into the private pavilions at the sleek and serene Amanyara (which offers open-air pavilion rooms with direct ocean access, as well as free-standing villas with infinity pools) or the exclusive villas at COMO Parrot Cay, 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 & COVID-19 Safety: As of October 14, all travelers to the Turks and Caicos must obtain travel pre-authorization, which requires negative results from a COVID-19 PCR test taken within five days prior to departure at an accredited laboratory; travel medical insurance; and a completed online health screening questionnaire. All travelers will be subject to screening and temperature checks upon arrival, which may result in further examination. U.S. citizens who do not prove to have been exposed to COVID-19 will not be required to quarantine (source: U.S. Embassy in The Bahamas Website).

Related: Indagare’s Turks and Caicos Matchmaker

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

Just 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. For a well-rounded and reliably luxurious resort experience, the Ritz-Carlton St. Thomas provides the ideal home base.

Entry Requirements & COVID-19 Safety: As of October 14 (and as a United States Territory), the U.S. Virgin Islands are open to U.S. citizens. Via the USVI Travel Screening Portal, travelers must provide proof of either: negative results from a COVID-19 antigen (molecular/PCR/rapid) test received within five days of departure, or positive results from a COVID-19 antibody test received within four months of departure. Upon arrival, travelers must show their original test results and travel certification received from the USVI Travel Screening Portal. Travelers must wear masks in the airport and submit to health screening and temperature checks (source: U.S. Virgin Islands Travel Screening Portal).

Related: Ask Indagare: Coronavirus Travel Safety & What is Being Done as the World Reopens

Best Caribbean Island for a Quiet, Private Retreat: Canouan Island and Mustique, Saint Vincent and the Grenadines

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 (reopening November 1)—while the tiny gem that is Canouan Island is truly quiet, and is best enjoyed from the Mandarin Oriental.

Entry Requirements & COVID-19 Safety: As of October 14, Saint Vincent and the Grenadines are open to American citizens. Travelers from the U.S. must complete a pre-arrival questionnaire form and present negative results from a COVID-19 PCR test taken no more than five days before arrival. Travelers may be retested upon arrival. Travelers to Mustique are not currently required to quarantine. Travelers to other parts of Saint Vincent and the Grenadines must complete a mandatory five-day quarantine at a government-approved hotel. Between Day Four and Five of the stay travelers must be tested for a third time, before release from quarantine in the approved hotel. Travelers may be required to continue to quarantine for nine-to-16 days in the approved accommodation at the discretion of the Port Health Officer (source: U.S. Embassy in Barbados, the Eastern Caribbean, and the OECS Website).

Related: Private Charter Flights: What to Know Now

Best Caribbean Island for a Low-Key Escape: Harbour Island, the Bahamas

This tiny Bahamian island known as “Briland” to both vacationers and locals 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. Outside of Harbour Island, other top Indagare picks in the Bahamas include the Ocean Club, a Four Seasons Resort, and Rosewood Baha Mar (open November 22), both in Nassau.

Entry Requirements & COVID-19 Safety: As of October 14, the Bahamas and Harbour Island are open to U.S. citizens. Prior to traveling—whether by boat or by plane—all U.S. citizens must submit a travel health visa application online, which requires proof of a negative COVID-19 RT PCR test taken no more than five days prior to the date of arrival. Applications take up to 72 hours to process; each traveler must present their final application confirmation and negative COVID-19 RT PCR test results upon arrival. All travelers entering the Bahamas must quarantine for 14 days or the duration of stay (if shorter than 14 days) upon arrival; travelers may quarantine in a private residence, rented accommodation, hotel, private club or private boat. Travelers must submit to monitoring by the Bahamian government through a downloaded mobile app (source: U.S. Embassy in The Bahamas Website).

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

Best Caribbean Island for an All-Inclusive 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 & COVID-19 Safety: As of October 14, the Dominican Republic is open to U.S. citizens. A negative COVID-19 PCR test is not required for entry; however, COVID-19 rapid tests will be performed on randomly selected travelers upon arrival. Only travelers who test positive will be required to quarantine. Temperature checks may also be implemented upon arrival or departure. Additionally, as of September 15, the Dominican government is extending complimentary travel and medical insurance to all travelers (until December 31st, 2020), which will cover all emergency hospitalization, medical, lodging, and airline ticket change fees, should the traveler contract COVID-19 while in the Dominican Republic. There are no restrictions on interstate travel, but there is a nationwide curfew from Monday through Friday from 9 p.m. to 5 a.m. and on weekends from 7 p.m. to 5 a.m. (source: U.S. Embassy in the Dominican Republic Website).

Related: Direct Flights to the Caribbean

Best Caribbean Island for Five-Star Family Fun: Antigua

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 the upscale, all-inclusive Jumby Bay (reopening November 7), offering a private island location, friendly atmosphere and top-notch amenities on a breathtaking beachfront, while Antigua’s first luxury hotel, Curtain Bluff (reopening October 24), 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 & COVID-19 Safety: As of October 14, Antigua & Barbuda are open to American citizens. All travelers arriving by air must provide documentation of a negative COVID-19 RT-PCR test taken within seven days of their flight. All travelers must complete a health declaration form and will be subjected to screening and temperature checks by health authorities upon arrival. Travelers will be monitored for COVID-19 symptoms for periods of up to 14 days in accordance with guidelines of the Quarantine Authority and may be required to undergo testing for COVID-19 upon arrival or at the hotel or place of lodging, as determined by the health authorities. Travelers arriving by sea (including private yachts and ferries) are subject to quarantine according to guidelines issued by Port Health and are also subject to assessment by health authorities (source: U.S. Embassy in Barbados, the Eastern Caribbean, and the OECS Website).

Related: Where to Go for the Holidays—And What to Know Before You Go

Best Caribbean Island for an Elegant Escape: Barbados

A tropical paradise 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 (reopening November 1), a former playground for British royalty, still maintain a slightly formal air with lavish accommodations, fine dining and a glamorous clientele.

Entry Requirements & COVID-19 Safety: As of October 14, Barbados is open to American citizens. Travelers from high- and medium-risk countries (the U.S. has been deemed a high-risk country) are required to take a COVID-19 PCR test from an accredited or certified facility/laboratory within 72 hours prior to arrival and present documentation of negative results. All travelers must also complete and submit an online immigration form 24 hours prior to travel. Travelers will be quarantined at their chosen designated hotel or government-approved villa and will be monitored for the onset of symptoms for a period of 14 days. Travelers must take a second COVID-19 PCR test between four and five days after the last negative test accepted by the Barbados Ministry of Health. Travelers will typically be released from quarantine once the test result is negative (source: U.S. Embassy in Barbados, the Eastern Caribbean, and the OECS Website).

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 and Jade Mountain—and a dramatic, mountainous terrain, plus world-class diving and a vibrant arts scene, St. Lucia promises to satisfy the travel-craved, who are looking for a beach retreat with a bit more soul.

Entry Requirements & COVID-19 Safety: As of October 14, St. Lucia is open to American citizens. Travelers must complete a pre-arrival travel registration form no less than three days before departure and present negative results from a COVID-19 PCR test taken no more than seven days before arrival. All travelers will be screened and must submit to temperature checks upon arrival. Travelers must have confirmed reservations at a COVID-19-certified accommodation provider (hotel or private residence) for the duration of their stay, where they will be required to remain on property, except to transfer to another COVID-19-certified property to continue their stay and to participate in water-based excursions arranged by the hotel. Guests may not leave the property by vehicle or on foot during their stay (source: U.S. Embassy in Barbados, the Eastern Caribbean, and the OECS Website).

Related: Easy Beach Getaways

Best Caribbean Island for a Classic Holiday: Bermuda

A mid-Atlantic island, Bermuda is famous for its colonial architecture, pink-sand beaches and crystal blue waters. Great Britain’s oldest existing colony still feels traditionally English, but its proximity to the U.S. means there is a strong American influence. After a heyday in the 1960s, 70s and 80s, the 21-square-mile isle has been popular with families looking for a quick escape, business travelers and with cruise ships. Today the island is buzzing with luxury hotel and restaurant openings and there are an abundance of activities on and off the water, with top hotels including The Loren and the Rosewood Bermuda.

Entry Requirements & COVID-19 Safety: As of October 14, Bermuda is open to U.S. citizens. Prior to arrival, travelers must complete the Bermuda travel authorization online (a $75 fee is required, which includes the cost of the PCR COVID-19 testing in Bermuda). Upon arrival, travelers must present this authorization form and negative results from a certified PCR COVID-19 test, taken ideally within 72 hours of departure, but no more than seven days before. At the airport, travelers must submit to health screening and a non-contact temperature check, as well as an additional PCR COVID-19 test. Travelers must quarantine at home or in their room at their reserved accommodation until results are ready (turnaround time is approximately 24 hours in most cases, though results may take longer depending on arrival time). Upon receipt of negative results, travelers will be released from quarantine. Anyone who becomes COVID-19 positive, or whom health authorities believe could be positive, will be subject to public-health regulations and will be isolated at their accommodation for up to 14 days, and will be fitted with an Aqua electronic bracelet to assist with isolation/quarantine. (source: U.S. Consulate General in Bermuda).

Related: The Indagare Guide to Armchair Travel: Films, Playlists, Recipes and More from Around the World

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 Spanish, American and indigenous cultures, as well as white-sand beaches and tropical rainforests ripe with adventure. One of the very best resorts on the island is the Ritz Carlton Reserve at Dorado Beach, which sits on a three-mile stretch of sandy paradise past lush gardens overflowing with coconut palms, growing pineapples and the sounds of coqui frogs chirping. In addition to the 100 guest rooms and 14 one-bedroom suites that are spread across 11 two-story buildings, the property has two-, three-, four- and five-bedroom private residences, which are available for weekly rentals and are ideal for families traveling with kids or those looking for a higher level of privacy and space.

Entry Requirements & COVID-19 Safety: As of October 14 (and as a United States Territory), Puerto Rico is open to U.S. citizens. Travelers must complete a travel declaration and provide proof of a negative COVID-19 molecular-based (RT-PCR) test taken no more than 72 hours prior to arrival. Upon arrival, travelers must wear a mask during disembarkation and submit to health screening and temperature checks (source: Discover Puerto Rico website). 

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, destinations that are open to travel, 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, 2020

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