Updated July 25th 2025
You want sun on your face, and your toes deep in the kind of sand that makes you question every life choice that doesn’t involve a beach. I get it. But you don’t want to deal with layovers, missed connections, or sprinting through airports like you’re auditioning for an action movie.
Good news: paradise is now just one flight away.
If you’re flying out of Boston Logan (BOS) and dreaming of the Caribbean, buckle up—because we’ve pulled together the ultimate list of direct flights from Boston to Caribbean hotspots that’ll get you from “ugh, work emails” to “pass the jerk chicken” faster than you can say “boarding group three.”
Whether you’re vibing with Jamaica’s music-filled streets, craving Turks and Caicos’ whisper-quiet luxury, or eyeing Aruba’s never-ending sunshine, Haute Retreats has the lowdown. We’re talking real-deal, nonstop routes, the best airlines to get you there, and maybe a few suggestions for which villa you should be sipping your welcome cocktail in once you land.
Let’s jump into the sunny side of life, shall we?
Here’s where you can fly direct from Boston to the Caribbean—because layovers are so last season.
Barbados
Airlines: JetBlue
BOS to Barbados Flight Time: 4hr 49min | Airport Code: BGI
JetBlue runs direct flights from Boston to Barbados. This island suits people who want to relax and seek thrills. You can chill on Paynes Bay Beach or explore Harrison’s Cave. Barbados has everything. Barbados also boasts some of the most luxurious villas in the Caribbean.
Bahamas
Airlines: JetBlue and Delta Airlines
BOS to Nassau Flight Time: 3hr 43min | Airport Code: NAS
JetBlue and Delta Airlines run nonstop flights to the Bahamas from Boston touching down in Nassau. Once there, you can reach other islands by air or sea. Think about swimming with pigs in Exuma or exploring the underwater world at the Andros Barrier Reef—all after a single flight.
Grand Cayman
Airlines: JetBlue
BOS to Grand Cayman Flight Time: 4hr 5min | Airport Code: GCM
JetBlue offers direct flights from Boston to Grand Cayman. If you like diving you will enjoy exploring the well-known underwater cliffs and sunken ships, while others can indulge in upscale shopping and eating on Seven Mile Beach. We recommend booking a vacation home at Seven Mile Beach or Rum Point.
St. Martin
Airlines: JetBlue
BOS to St Martin Flight Time: 4hr 12min | Airport Code: SXM
JetBlue has direct flights from Boston to St. Martin. You can taste the tasty food, check out both the French and Dutch parts of the island, and relax on the stunning beaches.
Turks and Caicos
Airlines: JetBlue and American Airlines
BOS to Providenciales Flight Time: 3hr 59min | Airport Code: PLS
JetBlue and American Airlines offer non-stop flights from Boston to Turks and Caicos landing in Providenciales.
You can swim in the clear waters, check out Grace Bay Beach, and relax on this pretty island.
Dominican Republic
Airlines: JetBlue, American Airlines and Delta Airlines
BOS to Punta Cana Flight Time: 4hr 11min | Airport Code: PUJ
JetBlue, American Airlines and Delta Airlines provide non-stop flights from Boston to Punta Cana. This Dominican paradise attracts visitors with its stunning beaches and all-inclusive resorts making it ideal for romantic getaways or family vacations.
Punta Cana boasts 5-star properties with top-notch golf courses, which have a strong appeal to golf lovers.
Jamaica
Airlines: JetBlue, Delta and American Airlines
BOS to Montego Bay Flight Time: 4hr 21min | Airport Code: MBJ
JetBlue, Delta Airlines and American Airlines offer non-stop flights from Boston to Jamaica.
Soak up Jamaica’s relaxed atmosphere, check out the Bob Marley Museum, or take a trip down the Martha Brae River—without any stops along the way.
St. Thomas, US Virgin Islands
Airlines: JetBlue (Delta launching soon)
BOS to St. Thomas Flight Time: ~4hr 10min | Airport Code: STT
Looking to escape to the U.S. Virgin Islands without the hassle of layovers? You’re in luck—JetBlue offers nonstop flights from Boston to St. Thomas during peak travel seasons, typically once a week. And starting in December 2025, Delta will also launch direct Saturday service to this island paradise. Whether you’re snorkeling in Magens Bay or strolling through Charlotte Amalie, getting there just got a whole lot easier.
Anguilla
Airlines: BermudAir (Anguilla Air)
BOS to Anguilla Flight Time: ~6hr | Airport Code: AXA
Big news for travelers craving something a little more exclusive—Anguilla is getting its first-ever direct flight from Boston. Starting December 20, 2025, boutique airline BermudAir (operating as “Anguilla Air”) will fly nonstop from BOS to Anguilla twice a week (Wednesdays and Saturdays) during the winter season. That means no more connecting in St. Martin or San Juan. With this new seasonal route, luxury-seekers can land just minutes away from Anguilla’s world-class beaches and upscale retreats.
Anguilla Villas by Haute Retreats
No matter which Caribbean island you fall in love with direct flights from Boston make it easy to reach your dream spot. So pack your bags, make sure your passport is up to date, and get ready for a non-stop trip to paradise.
If flying commercial isn’t your thing and you’d rather go private, take a look at our guide on how to rent a private jet.
Your Caribbean trip is just a plane ride away!
