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Flights to Anguilla

Fly to Anguilla in comfort and style with Tradewind scheduled flights from San Juan and private charter flights from the U.S., Puerto Rico, the USVI and Antigua. 

Major Airline Hub Convenience

With hubs in San Juan, Puerto Rico, Antigua and the U.S. Virgin Island of St. Thomas, passengers can easily connect with virtually all major airlines from the U.S., Canada, Europe and South America. Better yet, the customs and immigration process for Americans traveling through Puerto Rico is vastly eased given Puerto Rico is a U.S. Territory.

Additionally, at San Juan we operate our own private lounge where Tradewind passengers may relax and enjoy the refreshments and WIFI before flight time. Also available at San Juan is our “VIP meet and greet” service for smooth and stress-free transfers between flights ($200 per group arriving on the same airline flight).

Modern Aircraft Comfort and Safety

Shuttle flights are operated in Swiss-built Pilatus PC-12 jet-prop aircraft flown by two pilots with air-conditioning, a pressurized cabin and plenty of room for luggage. Enjoy complimentary snacks and refreshments including wine and beer onboard.

Flexible Ticket Terms

Itinerary changes are free and shuttle tickets are interchangeable with family and friends. Luggage is free (max 50 lbs / 23 kg total per person) and pets are welcome at no charge (limit one party with pets per flight).

Private Jet Connections

Connecting from your private jet? Our local team will meet your aircraft arrival for a smooth transfer to the your local Tradewind connection.


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

  • 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

>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.