Anguilla Expands Winter Air Service From North America

For a certain kind of traveler, Anguilla has always been the Caribbean’s best-kept open secret — 33 beaches that consistently rank among the region’s finest, a food scene that punches well above its size, and a studied absence of mega-resorts or cruise-ship crowds. The catch has always been getting there. This winter, that catch gets noticeably smaller.

AnguillAir, announced a significant expansion of its winter schedule, adding a brand-new route from Canada and boosting frequencies across several of its core U.S. gateways — a move that should make an island long associated with logistical hassle considerably more accessible.

The Headline Addition: Toronto

The marquee new route connects Toronto Pearson International Airport to Anguilla via Providenciales, Turks and Caicos, with weekly Saturday service beginning Dec. 19 and running through May 1, 2027. It’s Anguilla’s first meaningful direct-adjacent link to the Canadian market via this carrier, opening the island to a segment of travelers who’ve historically had to route through Miami, San Juan or St. Maarten and then connect onward by ferry or small aircraft.

More Frequency From Existing U.S. Markets

Beyond the Canadian debut, AnguillAir is padding out its American schedule from mid-December:

• Boston moves to twice-weekly nonstop service (Mondays and Fridays).
• Newark also goes twice-weekly nonstop (Mondays and Fridays), with an additional Saturday routing via Providenciales.
• Baltimore-Washington adds weekly nonstop service on Mondays plus a Thursday flight via Providenciales.
• Tampa/St. Petersburg gets new twice-weekly service (Thursdays and Saturdays) via Providenciales.

All routes fly on Embraer E190 aircraft configured in a two-class layout with no middle seat — a small but meaningful comfort detail on a route network built around leisure travelers rather than business commuters.

Why the Timing Matters

The expansion lands as Anguilla continues to bank serious accolades from the TripCast360 readers. The island has been named the top pick in the Caribbean, Bermuda and Bahamas category by Travel + Leisure readers five times in recent years, recently earning induction into the magazine’s Hall of Fame after a decade of sustained recognition in its World’s Best Awards. That’s the kind of validation that tends to translate into real demand — but only if airlift can keep pace, which has historically been Anguilla’s Achilles’ heel.

Anguilla’s Minister of Infrastructure, Hon. José Vanterpool, framed the expansion as more than a scheduling update, noting it strengthens regional and international connectivity while reinforcing ties across British Overseas Territories in the region. Minister of Health, Tourism and Sport Hon. Cardigan Connor added that the increased flight volume translates directly into more opportunities for the island’s small-business tourism economy.

BermudAir Founder and CEO Adam Scott, for his part, positioned the expansion as part of a broader multi-island Caribbean network strategy the carrier has been building out, with Anguilla and Bermuda as its current anchor points.

If you’ve wanted to visit Anguilla but balked at the logistics — often a flight into St. Maarten followed by a ferry transfer, with all the timing risk that entails — these new routes meaningfully shrink the friction. A direct path from Toronto, or an easier nonstop from Boston, Newark, Baltimore or Tampa, changes the calculus for a long weekend trip in a way connecting itineraries never could.

It’s also worth noting the routing through Providenciales on several of these flights, which effectively bundles two of the Caribbean’s most celebrated beach destinations into a single itinerary — useful if you’re the type of traveler who likes to stack islands rather than commit to just one.

For travel advisors, this is a genuinely useful selling point going into the winter booking season: now meaningfully easier to reach from three new North American markets. Expect Anguilla’s already-strong luxury villa and boutique resort sector to see continued demand pressure as awareness catches up with access.

Anguilla’s tourism authority has made clear this expansion builds on a first season of AnguillAir service that officials characterized as successful. If that momentum holds, don’t be surprised to see further route additions in future winters — particularly if the airline continues to treat Anguilla as a flagship destination in its broader Caribbean network strategy.