For a tropical vacation in the Caribbean, you really can’t go wrong no matter which island you choose. But if you’re looking for an escape that’s easy to get to, you’ll want to consider a Caribbean destination with a lot of direct flights from North America.
If you live on the East Coast or in the middle of the United States, direct flights are offered year-round or frequently throughout the year. Your options are slimmer on the West Coast, but there are still seasonal routes from major hubs like Los Angeles and Seattle. You’ll also find occasional flights from cities like Toronto and Montreal on global alliance partner airlines such as Air Canada, among other carriers. Here are the Caribbean islands with the most direct flights from the United States and Canada.
Puerto Rico
Part of the Greater Antilles, Puerto Rico sits between the Atlantic Ocean to the north and the Caribbean Sea to the south. More than 120 daily nonstop flights run between the U.S. territory and major cities all over the U.S., including Miami, Tampa, Orlando, Charlotte, Philadelphia, Baltimore, Newark, New York, Providence, Boston, Chicago, Houston, Cleveland, and Denver. There are also seasonal flights from Toronto to San Juan.
Airlines that fly between Puerto Rico and the U.S. include Frontier, American, Delta, JetBlue, Southwest, United, and Sun Country. Flights from Toronto are typically on Air Canada or WestJet. So no matter where you live, it’s easy to get to the island to explore sites like Old San Juan, Flamenco Beach, and El Yunque National Forest (the only tropical rainforest within the U.S. forest system).
Where to stay: Condado Vanderbilt Hotel and San Juan Marriott Resort & Stellaris Casino are good options near Old Town San Juan. If you want to stay near El Yunque, we recommend Wyndham Grand Rio Mar Rainforest, Beach & Golf Resort, which recently completed a multimillion-dollar redesign of its rooms and suites, dining venues, pool decks, and public spaces.
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Turks and Caicos
This island archipelago technically sits in the Atlantic Ocean southeast of The Bahamas, but it’s considered part of the Caribbean region. Many travelers head to the island of Providenciales for the beaches of Grace Bay, regarded as some of the most beautiful in the world.
Direct flights land at Providenciales International Airport (PLS) from Atlanta, Baltimore, Boston, Charlotte, Chicago, Dallas, Detroit, Houston, Miami, Minneapolis, Newark, New York, Philadelphia, and Washington D.C. Less frequent routes are operated from cities such as Denver and Orlando. There’s also a direct flight from Miami to South Caicos (XSC).
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Where to stay: Grace Bay Resorts consists of six distinct boutique properties, including the family-friendly Grace Bay Club and Southbank. Both resorts excel in offering space, privacy, and an authentic cultural experience. Another popular choice is Beaches Turks and Caicos, an all-inclusive option with a bigger family resort feel.
Aruba
The “Happy Island” of Aruba welcomes more than 100 nonstop flights weekly from the U.S. That includes American Airlines flights from Miami, Charlotte, Philadelphia, and Dallas; United Airlines flights from Newark, Washington D.C., and Houston; JetBlue flights from Boston and New York; and flights from Atlanta on Delta and Orlando on Southwest. There’s also seasonal service from Chicago. Meanwhile, Air Canada offers regular service from Toronto to Oranjestad; other Canadian carriers run seasonal routes.
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Once you land on the Dutch Caribbean island, enjoy beautiful Caribbean beaches, the vibrant arts scene in San Nicolas, the dramatic landscapes at Arikok National Park, and Oranjestad’s famous Dutch architecture.
Where to stay: Embassy Suites by Hilton Aruba provides excellent value but still plenty of perks. Divi & Tamarijn Aruba All-Inclusive Resorts offer a two-for-one kind of experience.
The Bahamas
There are currently 73 direct flights to The Bahamas from the U.S., with the most landing at Lynden Pindling International Airport (NAS) in Nassau. Commercial flights from American, Delta, JetBlue, and United arrive regularly there from cities like Atlanta, Charlotte, Dallas, Miami, Denver, New York, Fort Lauderdale, Newark, Orlando, Houston, and Washington-National. Breeze Airways also recently started offering nonstop service from Tampa to Nassau on select days.
The options from Canada are surprisingly abundant. Regular non-stop flights operate from Montreal and Toronto. Other carriers occasionally offer seasonal flights from cities like Vancouver, Ottawa, Halifax, and Calgary.
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Aside from Nassau, other airports on the island archipelago (which technically lies in the Atlantic Ocean but is considered culturally part of the Caribbean) welcome direct flights from the U.S.
Flights from Miami, Fort Lauderdale, and Charlotte land daily at Leonard M. Thompson International Airport (MHH) in Marsh Harbour, while flights from those cities plus Atlanta touch down each day at North Eleuthera Airport (ELH). American Airlines also operates the only regularly scheduled nonstop service from the United States to Bimini, three times a week. The Bahamas Ministry of Tourism has a handy breakdown of all the flights to each Bahamas airport, here.
Where to stay: Kids and teens will love all the splashy amenities at Atlantis Bahamas. For more lowkey luxury, take your family to the nearby Rosewood Baha Mar.
Jamaica
If you want to fly into Montego Bay International Airport (MBJ), you can catch a direct flight throughout the year from cities like Atlanta, Baltimore, Charlotte, Chicago, Dallas, Minneapolis, Detroit, Fort Lauderdale, Miami, Newark, New York, Orlando, and Philadelphia. A number of other U.S. cities have seasonal or less frequent service, including Kansas City and St. Louis. From Canada, regular nonstop flights are offered from Montreal, Toronto, and Halifax, while seasonal direct routes run from Calgary. (You can find the full list here.)
The airport in Montego Bay handles the vast majority of flights to the island. But direct flights also land regularly at Norman Manley International Airport (KIN) in Kingston from Miami, New York, Fort Lauderdale, and Atlanta on American, JetBlue, and Spirit Airlines.
Where to stay: Montego Bay’s iconic Half Moon resort has been meticulously renovated to feel fresh and modern while retaining its historic charm. Some of the best all-inclusive resorts for families in Jamaica also include Beaches Negril, Hyatt Ziva Rose Hall, and Bluefields Bay.
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U.S. Virgin Islands
Want to vacation on Saint Thomas? You can catch a direct flight from cities that include Atlanta, Baltimore, Boston, Charlotte, Chicago, Detroit, Dallas, Fort Lauderdale, Houston, Miami, Minneapolis, New York-, Newark, Orlando, Philadelphia, San Juan, and Washington D.C..
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If you’d rather get away to Saint Croix, you can fly directly from Atlanta, Charlotte, Chicago, Newark, and Miami. And no passports needed to travel to either location, since the Virgin Islands are a U.S. territory.
Where to stay: Consider Hampton by Hilton St. Thomas for a reliable family-friendly stay with an outdoor pool and free daily hot breakfast. A newly unveiled option, The Botany offers an intimate escape with only 20 villas. The Buccaneer is a traveler favorite on Saint Croix.
Saint Martin/Sint Maarten
Flying to Saint Martin/Sint Maarten involves a famous landing experience over Maho Beach, where beachgoers watch the skies along with the waves. SXM Princess Juliana Airport welcomes flights from Atlanta, Baltimore, Boston, Charlotte, Chicago, Fort Lauderdale, Miami, Orlando, Dallas, New York, Newark, Philadelphia, Washington D.C., Montreal, and Toronto. During the winter months, Minneapolis also operates nonstop service.
When you’re not watching dramatic touchdowns from the beach, you can spend your time on the island hiking, kayaking, and braving the steepest zipline in the world.
Where to stay: Sonesta Maho Beach Resort, Casino, and Spa offers a fun kids club for young guests as well as teen zone. JW Marriott St. Maarten Beach Resort & Spa sits along Dawn Beach and features rooms and suites with ocean views.
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Saint Lucia
A trip to Saint Lucia is always a good idea, and you can catch regular nonstop flights year-round from New York, Miami, Charlotte, Atlanta, Boston, Newark, Chicago, and Toronto.
The island in the eastern Caribbean is often called the “Hawaii of the Caribbean” because of its lush rainforests, dramatic landscapes, and iconic twin volcanic peaks, the Pitons. Families, in particular, love St. Lucia because it blends otherworldly scenery, outdoor adventure, and slower-paced beaches in one “compact” package.
Where to stay: With waterslides, a lazy river, and kids club, Coconut Bay Beach Resort & Spa is family vacation heaven. Those seeking more space can enjoy the stunning backdrop and adventure that awaits at Windjammer Landing Resort & Residences.
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The Cayman Islands
If the Cayman Islands are on your travel bucket list, you can catch a direct flight to Owen Roberts International Airport on Grand Cayman from cities like Atlanta, Charlotte, Houston, Miami, Tampa, New York, and Toronto. Other cities that offer seasonal or intermittent service include Orlando, Baltimore, Boston, Dallas, Denver, Minneapolis, and Ottawa. For the full list of cities and flight frequency, click here.
Part of the British Overseas Territories, the Cayman Islands are just 480 miles south of Miami, so they’re relatively easy to get to. Families seek out this destination for its shallow beaches, solid infrastructure, and myriad kid-friendly attractions including botanical gardens and sea turtle sanctuaries.
Where to stay: The Westin Grand Cayman Seven Mile Beach Resort & Spa, Kimpton Seafire Resort + Spa, and Grand Cayman Marriott Resort are some of the best Seven Mile Beach resorts for families on Grand Cayman.
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Dominican Republic
Almost 30 percent of the flights arriving each month at Las Americas International Airport in Santo Domingo, Dominican Republic, originate from New York City and Miami. Other cities with year-round direct flights to Santo Domingo include Atlanta, Boston, Fort Lauderdale, and Orlando, while there’s seasonal service from cities like Philadelphia and Tampa.
If you’d rather fly into Punta Cana International Airport, you can get a direct flight from Chicago, Denver, Hartford, Indianapolis, Miami, Nashville, Orlando-Sanford, Pittsburgh, and Raleigh-Durham. The country has eight international airports in total, so you’ll want to start by looking into the options closest to your final destinations. Canadian cities such as Quebec, Montreal, and Toronto also offer flights to the Dominican Republic throughout the year.
Where to stay: Club Med Punta Cana recently unveiled new deluxe rooms and dining options, and Nickelodeon Hotels & Resorts Punta Cana is always a popular pick for families with younger kids. The new, all-inclusive Lopesan Caoba Lagoon Resort, Spa & Casino also is already gaining traction as a top choice for families.
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