AnguillAir Returns to Anguilla for Winter 2026 with More Flights from the USA and Canada

Getting to Anguilla is becoming even easier this winter.

AnguillAir, the seasonal Anguilla brand operated by BermudAir, is returning for the 2026/27 winter season with an expanded schedule connecting Anguilla with key cities across the United States and Canada.

Following its first season, AnguillAir is increasing connectivity to the island with services from Boston, Newark, Baltimore/Washington, Toronto and the St. Petersburg/Tampa Bay area. Caribbean Tourism Authority

For visitors planning a winter escape to Anguilla, that means more ways to reach the island and begin enjoying its beaches, restaurants, resorts and unmistakably relaxed Caribbean lifestyle.

And once you arrive at Clayton J. Lloyd International Airport, Gumbsie Car Rental can help you take care of the next part of your journey.

What Is AnguillAir?

AnguillAir is the seasonal Anguilla-focused brand operated by BermudAir.

It is important to make that distinction: AnguillAir is not a separate airline. All AnguillAir flights are operated by BermudAir and use the airline’s aircraft and service. BermudAir describes AnguillAir as a seasonal sub-brand forming part of its wider island aviation network. AnguillAir

For travellers, however, the AnguillAir name has a very clear purpose: connecting North American visitors with Anguilla.

The 2026/27 winter programme expands that concept considerably.

When Does AnguillAir Return to Anguilla?

AnguillAir’s main winter services return from 18 December 2026.

According to BermudAir’s currently published schedule, nonstop flights from Boston and Newark begin on Friday, 18 December 2026. Toronto service begins the following day, 19 December 2026. BermudAir

The seasonal programme continues into spring 2027, making the service particularly useful for visitors planning Christmas, New Year, winter and early-spring holidays in Anguilla.

As airline timetables can change, passengers should always confirm their specific travel dates directly with AnguillAir or BermudAir before booking other travel arrangements.

Boston to Anguilla

Travellers from New England will once again have a particularly convenient way to reach the island.

AnguillAir’s Boston Logan International Airport (BOS) to Anguilla (AXA) service is scheduled to operate nonstop on Mondays and Fridays from 18 December 2026.

The service continues into May 2027, although the precise schedule varies later in the season. BermudAir

For travellers accustomed to making connections elsewhere in the Caribbean or United States, being able to board in Boston and step off the aircraft in Anguilla makes planning an island holiday considerably simpler.

Newark to Anguilla

The New York metropolitan area will also have expanded AnguillAir connectivity.

BermudAir’s published schedule includes nonstop Newark (EWR) to Anguilla flights on Mondays and Fridays, beginning 18 December 2026.

Additional services operate on other days during parts of the season, including direct services with intermediate stops. BermudAir

This gives travellers from New York, New Jersey and surrounding areas significantly more choice when planning an Anguilla holiday.

Baltimore/Washington to Anguilla

The Baltimore and Washington region is another important part of AnguillAir’s winter programme.

The expanded service provides another option for travellers from the Mid-Atlantic region to reach Anguilla without relying solely on the traditional Caribbean connecting gateways.

Together with Boston and Newark, it strengthens Anguilla’s direct air links with several major population centres on the US East Coast. Caribbean Tourism Authority

A New Toronto to Anguilla Connection

One of the biggest additions for winter 2026/27 is Toronto.

Beginning Saturday, 19 December 2026, BermudAir is scheduled to operate a weekly service from Toronto Pearson International Airport (YYZ) to Anguilla via Providenciales in the Turks and Caicos Islands.

The service is scheduled to continue through 1 May 2027. Caribbean Tourism Authority

This provides Canadian travellers with a new way of reaching Anguilla during the winter season.

For Anguilla, the significance goes beyond another flight.

Canada represents a substantial outbound winter travel market, and improved access gives more Canadian travellers the opportunity to discover an island that offers something quite different from many larger Caribbean destinations.

Anguilla Connections from St. Petersburg and Tampa Bay

Florida travellers also gain another option.

The winter programme includes service between St. Pete-Clearwater International Airport (PIE) and Anguilla.

The currently published schedule shows the southbound PIE to AXA journey operating via Providenciales, rather than as a nonstop flight. BermudAir

It nevertheless creates an additional link between Florida’s Tampa Bay region and Anguilla and further broadens the island’s North American connectivity.

Why More Flights Matter for Anguilla

For a small island destination, air connectivity matters enormously.

Anguilla has long attracted visitors looking for beautiful beaches, exceptional restaurants, luxury accommodation and a quieter Caribbean experience.

But reaching the island has traditionally required many travellers to connect through another Caribbean destination.

More services into Clayton J. Lloyd International Airport mean visitors have additional choices.

It also means that more of the visitor journey begins and ends in Anguilla itself.

That benefits hotels, villas, restaurants, local attractions, transportation providers and the many other businesses that make up Anguilla’s tourism industry.

33 Beaches and an Entire Island to Discover

Of course, getting here is only the beginning.

Anguilla is renowned for its 33 beaches, from internationally recognised stretches of white sand to smaller bays that visitors sometimes discover almost by accident. The island’s tourism promotion highlights those beaches alongside its dining and laid-back luxury experience. Caribbean Tourism Authority

There is Shoal Bay East with its brilliant turquoise water.

Meads Bay combines a spectacular beach with some of Anguilla’s best-known hotels, villas and restaurants.

Rendezvous Bay provides beautiful views towards neighbouring St. Martin.

Sandy Ground changes character throughout the day, from a relaxed waterfront setting to one of the island’s popular evening destinations.

Then there are Crocus Bay, Maundays Bay, Little Bay, Savannah Bay and many more.

The advantage of Anguilla is that you do not have to choose just one.

The Best Way to Explore Anguilla? Get Behind the Wheel

Anguilla is approximately 16 miles long, making it an ideal island to explore by car.

You could start your morning on one side of the island, find somewhere completely different for lunch and finish the day watching the sunset from another beach.

That flexibility is difficult to replicate if every journey has to be planned separately.

With your own rental car, there is no timetable.

If you see somewhere interesting, stop.

If somebody recommends a restaurant, go and find it.

If you love a particular beach, stay longer.

And if you wake up the next morning wanting to explore somewhere completely different, simply get in the car and go.

That freedom is one of the pleasures of an Anguilla holiday.

Arriving with AnguillAir? Gumbsie Can Meet You at the Airport

Gumbsie Car Rental offers convenient airport meet and greet at Clayton J. Lloyd International Airport (AXA).

If you are arriving in Anguilla with AnguillAir, arrangements can be made for your rental vehicle to be ready when you arrive.

Instead of landing and then worrying about how to reach a separate car rental location, you can begin the next stage of your trip at the airport.

Collect your vehicle, load your luggage and head towards your hotel, resort or villa.

And your Anguilla holiday begins.

Staying at a Villa or Hotel?

Not everyone needs to collect their vehicle immediately at the airport.

Gumbsie Car Rental can also arrange vehicle delivery to villas and hotels around Anguilla, giving visitors additional flexibility depending on their travel plans.

Whether you are staying in West End, near Meads Bay, around Shoal Bay or elsewhere on the island, we aim to make the rental process as straightforward as possible.

Driving in Anguilla

Visitors to Anguilla should remember that we drive on the left-hand side of the road.

Visitors also require a temporary Anguilla driver’s licence before driving on the island.

Once you are settled behind the wheel, having your own car opens up a completely different Anguilla experience.

You are no longer simply visiting your resort.

You are exploring the island.

An Exciting Winter for Travel to Anguilla

The return and expansion of AnguillAir comes at an exciting time for Anguilla’s air connectivity.

American Airlines is also returning with its Miami to Anguilla service in October 2026, while AnguillAir’s expanded programme follows in December.

Together, these services give travellers from several North American markets more options for reaching Anguilla directly or through convenient direct routings.

For visitors, that means more choice.

For Anguilla, it means greater opportunity to introduce new travellers to the island.

And for those of us who call Anguilla home, it means another opportunity to welcome you.

Planning Your Anguilla Holiday for Winter 2026/27?

If you are considering Anguilla for Christmas, New Year or a winter escape, it is worth making arrangements early.

Flights, popular hotels, villas and rental vehicles can become limited during the busiest periods of the season.

Once your AnguillAir flights and accommodation are confirmed, reserving your rental car means one more part of your trip is taken care of before you arrive.

Then comes the enjoyable part.

Deciding where to go first.

Fly to Anguilla. Collect Your Car. Discover the Island.

AnguillAir’s return for winter 2026/27 brings more flights, more gateways and more opportunities to discover Anguilla.

Whether you are travelling from Boston, New York/Newark, Baltimore/Washington, Toronto, the Tampa Bay area or connecting from elsewhere, your journey ultimately leads to the same place:

Anguilla.

Once you arrive, let Gumbsie Car Rental help you discover everything our island has to offer.

From Shoal Bay to Meads Bay, Sandy Ground to West End and all the unexpected places you find along the way, having your own vehicle gives you the freedom to experience Anguilla your way.

Book your Anguilla car rental with Gumbsie Car Rental and have your vehicle ready for your arrival.