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Flights to Anguilla

Tradewind offers schedule flights from San Juan, Puerto Rico.

  • Flights for the 2019/2020 season run December 20, 2019 – April 13th, 2020
    • Operating daily December 20th – January 5th
    • Then 4 days per week, Fridays – Mondays, January 6th – April 13
  • Tickets starting at $195 plus taxes and fees


Tradewind Shuttle scheduled flights are available to Anguilla from San Juan (SJU):

>Tradewind Shuttle

>With our interline partner United Airlines

Private Charter flights are available to Anguilla from San Juan and Antigua in our local fleet of Pilatus PC-12s and from the U.S. in our fleet of Citation Jets:

>Charter Inquiry Form

Getting to Anguilla

Just 17 miles long and 3 miles wide, the island of Anguilla is a relative sand-spit, lying flat in the Caribbean Sea between St. Martin and St. Barths. As a result, it offers some of the most gorgeous white sand beaches and aquamarine waters in all of the Caribbean. Shoal Bay East is particularly stunning with powder soft sand and varying shades of turquoise water. While Meads Bay features a string of tantalizing beachside cafes and bars, like Straw Hat, handedly luring beachcombers away from their beach walks. With the Greg Norman-designed golf course now being run by CuisinArt Hotel and a Jack Nicklaus course in the works, golfers can happily add Anguilla to their roster. Scuba and snorkeling enthusiasts will appreciate the clear waters and abundant underwater life.

Ultimately, though, Anguilla is best known for its coterie of delectable restaurants. So much so, that dining out and sampling the impressive international fare might just be considered the island’s main pursuit. From casual beachside shacks to long held traditional restaurants to fine dining, including trek-worthy options at the island’s renowned luxury accommodations, including the new Viceroy and the recently refurbished Malliouhana, the options are quite remarkable for an island so tiny.

Know Before You Go

1. Taxis on island can be surprisingly expensive. If you are going to be there for quite some time, consider renting a car.

2. Don’t miss a visit the gardens at CuisinArt hotel, an impressive display of horticulture efforts in the middle of the Caribbean

3. Bankie Banx, a local reggae star, has his own beachside bar, Dune Preserve, which hosts musical acts including Banksie himself or his son, the cricket-cum-musical star.