New Flights Launching From 3 U.S. Cities To Lesser-Known Caribbean Paradise

Take it from someone who just visited St. Lucia for the first time that every island is definitely not a stone’s throw away.

Close proximity is one key reason islands like Jamaica and The Bahamas are so hugely popular, and Cuba would be too if it weren’t for, well, ya know…

Lost in the shadows of the more notable names are sunny paradises perfect for a winter escape as much of the U.S. mainland will be blanketed in snow, or at the very least endure teeth-chattering weather.

One such place is a lot more popular with our lads ‘across the pond’ given its British territory status — but no, we’re not talking about the British Virgin Islands.

A lesser-known airline is ready for takeoff to one of the Caribbean’s last remaining hidden gems by showcasing crowd-free white-sand shores, flashy beachfront resorts, and a reputation for being one of the Caribbean’s safest destinations for Americans up for an adventure without the same regurgitated itinerary.

A trio of busy airports is set to welcome 3 of only 4 U.S.-based flights here come December — the perfect time to not only escape the frigid holiday weather, but those dreaded family gatherings as well.

BermudAir Launching 3 New Flights To Anguilla 🇦🇮

As it stands today, and for quite some time, American Airlines is the only carrier serving Anguilla from the U.S.

Offering weekly flights from Miami (MIA), with the addition of BermudAir’s new flights in the coming months, travelers will soon have 4 direct options to reach this map-dot oasis.

So, who are the lucky winners to escape the throes of winter?

1) Boston:

If you thought you’d go to Boston and you thought you’d start a new life, your opinion may change once December’s bone-chilling temps roll around.

Sure, downing a beer and some Cracker Jacks at Fenway during summer makes Boston sound awesome, but once you’re in the midst of the holiday season and the turn of the calendar, the Caribbean will most certainly be living rent-free in your mind.

BermudAir’s first new flight to Anguilla (AXA) will launch from Boston (BOS) on December 17, 2025 on Wednesdays and Saturdays.

2) Newark:

No offense to one of New Jersey’s most populous city, but people here aren’t sticking around the Jersey side in favor of New York’s bright lights.

Though the appeal only lasts for so long before hordes of tourists trickle in to experience the magic of the “Big Apple” as a winter wonderland.

Serving as one of New York’s 3 major airports, you’ll see many “snowbirds” here flocking to sun-drenched shores, and now there’s another exciting option added to the mix.

BermudAir will launch Newark’s first flight to Anguilla on December 18, 2025 on every Thursday and Sunday.

3) Baltimore:

Baltimore may be the Northeast’s surprising new tourism hotspot, especially for foodies, but scarfing down delicious crabs isn’t a strong enough reason to stay in town and have to shovel your driveway each morning.

Or perhaps another Sunday of disappointing Ravens football will have you ready to get out of dodge.

Marylanders will soon have the chance for an easy escape to Anguilla from Baltimore (BWI), slated for launch December 19, 2025 on Fridays and Mondays.

Why Visit Anguilla For Winter Sun?

Even though kids are back in school and the grown-ups may have maxed out their PTO in summer, many Caribbean locales can still become crowded.

Anguilla is a rare place where there’s little to no concern.

Besides open beaches, you enjoy laid-back luxury with phenomenal resorts to choose from. At the top of the list, of course, is the Four Seasons Resort and Residences Anguilla at a premium price tag with a comma.

For those with a tighter budget, Shoal Bay Villa is a luxe coastal retreat along Anguilla’s popular Shoal Bay, laden with soft white sand, swaying palms, and a serene stretch of calm turquoise waters.

Though small, Anguilla doesn’t feel overdeveloped. There are plenty of remote pockets to find your own slice of paradise and now it’s easier than ever to reach.

Plus, according to Travel + Leisure, Anguilla was recently named the Caribbean’s safest destination.

The BermudAir Experience

Bermuda-based BermadAir has only been zooming through the clouds for a couple of years, but has impressively expanded its portfolio in a reasonably short period.

And so far, so good with defeating the legend of the Bermuda Triangle!

Don’t expect roomy Dreamliners or top-notch amenities — the aforementioned flights will be operated on a fleet of smaller Embraer jets.

BermudAir does offer an entertainment system (via your own device), complimentary refreshments, and isn’t as stringent as some of America’s budget airlines, offering a free carry-on no matter your class.

As they continue to grow, the little-known airline was crowned the 7th best airline in all of the Caribbean for 2025.