How to Get to Anguilla This Winter


Anguilla is one of the region’s buzziest luxury destinations — and if you’re heading there for the winter tourist season, there’s one great way to get there. 

The Caribbean’s leading luxury airline has relaunched its service to the island of Anguilla. 

Tradewind Aviation, which operates scheduled flights to some of the Caribbean’s most exclusive destinations (along with charter service across the region), has relaunched its flights from San Juan, Puerto Rico to Anguilla. 

From now through Jan. 5, the flights will be operating seven days per week. 

From Jan. 6-April 13, 2020, the Anguilla flights will be operating four times each week, with round-trip service on Fridays, Saturdays, Sundays and Monday. 

Tradewind, known for its luxe Pilatus PC12 service to destinations like St Barth, Nevis and Antigua, is unquestionably the best way to get to Anguilla, meaning travelers can cut out long immigration lines and waits at the ferry terminal and instead arrive in style directly at Anguilla’s Clayton J. Lloyd International Airport. 

Tradewind operates a VIP lounge on the second floor of San Juan’s Luis Munoz Marin International Airport, meaning travelers can arrive in Puerto Rico, check in and simply take the elevator directly to the boarding area and lounge. 

The stunning Nevaeh villa on Long Bay in Anguilla.

And Tradewind’s broad network of interline agreements, from airlines like United and British Airways, mean you can book your Anguilla itineraries on a single ticket — and check your bags all the way through Anguilla. 

Even better, Tradewind recently signed an interline agreement with American Airlines, too.

Anguilla has long had one of the Caribbean’s most opulent hotel products, from the iconic Cap Juluca to the Four Seasons to what is now a pair of CuisinArt-branded resorts. 

It’s a hotel product that continues to grow, from the new Relais & Chateaux Quintessence Hotel to Zemi Beach.

Anguilla’s newest hotel is the Quintessence, which is now part of Relais & Chateaux.

But Anguilla’s maritime arrival experience has often been less than luxurious, with excessive waits and processing times at the ferry terminal — making Tradewind the obvious choice for Anguilla’s luxury travelers. 

The relaunch of Tradewind is another boost for a destination that has seen record-breaking arrival numbers so far in 2019 — totals that actually surpassed the island’s previous all-time-high, set in 2017 before Hurricane Irma. 

And while its hotels are impressive, the ultimate way to experience Anguilla is at one of its ultra-luxe villas, from Nevaeh on Long Bay to the sleek Tequila Sunrise in Dropsey Bay

For more, visit Tradewind Aviation

— CJ