Search & Buy Tradewind Aviation Flights

Cabin class:



Please select an airport

Select a departure date

Search flights

Buy Tradewind Aviation Flights


Tradewind Aviation Reservations with Alternative Airlines


Make a Tradewind Aviation Booking and Find Some Amazing Deals



About Tradewind Aviation

Tradewind Aviation is an American Airline located in Oxford, Connecticut, United States. Tradewind Aviation provides executive private charter service throughout the world, shared charter in the Northeast and the Caribbean. Destinations in New England include Massachusets, NewJersey, New York, Vermont.


Tradewind Aviation was founded in 2001 and in October 2016, the airline announced a twice-daily service to Anguilla from San Juan. The service will operate twice daily, for a total of 4 scheduled flights operating between Anguilla and San Juan. The schedule facilitates connections to many airlines in the US and beyond, making it easier than ever to get to this vacation hotspot.


Passengers travelling with Tradewind Aviation are accommodated in a private Tradewind VIP lounge in San Juan International Airport (SJU). Tradewind Aviation operates Swiss-built Pilatus PC-12 aircraft flown by two pilots; features include air-conditioning, a pressurized cabin, comfortable leather seating and plenty of luggage room. On board amenities include complimentary snacks and drinks, including wine and beer, served on the 40-minute flight to Anguilla.


Tradewind Aviation Shuttle

Tradwind Aviation shuttle flights offer the comfort and convenience of a private charter for the cost of a single seat. In the U.S., scheduled Shuttle flights are operated from the New York area to Boston, Stowe, Nantucket and Martha’s Vineyard and depart from private charter FBO terminals. In the Caribbean, Shuttle flights are operated between San Juan, St Barths, Anguilla, Nevis, Antigua and St Thomas.


Tradewind Aviation Destinations

In the Caribbean destinations include San Juan, Saint Barthelemy, West Indies, Anguila and United States Virgin Islands.



Tradewind Aviation Frequent Flyer Program

Tradewind Shuttle flights have their own loyalty scheme called Tradewind Rewards. Every one-way flight you take grants you 10 points and after a mere 100 points, you get a free one-way flight! It's really easy to collect frequent flyer points with Alternative Airlines, just check out our airline alliance page for more information.


Alternative Airlines to Tradewind Aviation

Please click on the logos below to find out more about airlines that fly similar routes to Tradewind Aviation:


delta airlines logowestjet logoUnited airlines logo

Vieques Air Link logoAnguilla Air Services


Buy Tradewind Aviation Tickets at Alternative Airlines

Tradewind Aviation News

September 2017

ID Travel Group Foundation for Better Living to Raise Funds for Irma Relief

The ID Travel Group Foundation for Better Living has released an appeal to raise money for island nations affected by Hurricane Irma. The ID Travel Group's foundation will donate 100 percent of the proceeds to relief items and will fully match each donation up to $1,000.

The company has already made direct contributions to the relief effort. On September 12, Maurice Bonham-Carter- the president and CEO of ID Travel Group and the founder of the nonprofit foundation- and his Field Directors traveled to Anguilla and delivered more than 1,000 pounds of relief items to the locals in need of assistance.

Tradewind Aviation, a longtime partner of ID Travel Group, facilitated the delivery by providing private charter to the island from San Juan. The shipment of goods included essential materials like non-perishable food items, toiletries, mosquito repellent, and infant and senior care items.

“The people of these island nations are truly left in distress and this is just the beginning. They have no power or running water, and are desperate for everyday items such as mosquito repellant and filtered water,” said Bonham-Carter. “There is still much more to be done and Anguilla is just our starting point. The British Virgin Islands, St. Barths and neighboring islands are also in desperate need of assistance.”



May 2017

Tradewind Aviation announced it had added three new Pilatus PC-12 eight-seat aircraft to its fleet and added a new hub at Hanscom Field in Bedford, Massachusetts. Tradewind, which operates scheduled service from Westchester County Airport in White Plains, New York, now operates 21 aircraft, including 18 PC-12 turboprops and three Citation light business jets. It operates the second largest civilian Pilatus fleet in North America.



September 2015

Tradewind Aviation announce their newest Tradewind Shuttle with service between the Westchester Airport in White Plains, New York and Boston’s Logan Airport. As with our other routes, the Tradewind Shuttle provides the comfort and convenience of a private charter for the cost of a single seat. Tradewind Shuttle flights has a frequent flyer program called Tradewind Rewards to reward their regular passengers. In March 2017, Tradewind Aviation announced it was adding scheduled Boston-Westchester route. Tradewind Aviation has established itself as a private jet service to such tony leisure destinations as Martha's Vineyard, St. Barthelemy in the Caribbean and Vermont skiing destination Stowe.



Search and Buy Tradewind Aviation Flights

Make a Tradewind Aviation reservation and find some amazing deals with discounted Tradewind Aviation tickets at Alternative Airlines. Tradewind Aviation flies to many destinations offering a cost-effective and safe service to all its passengers. Let Alternative Airlines help find you cheap Tradewind Aviation tickets and make international and domestic flight reservations on Tradewind Aviation today.


Browse the most popular Tradewind Aviation flight routes to destinations worldwide. Alternative Airlines can help you make reservations on Tradewind Aviation for international flights to lots of destinations. Use the following list of routes to help you plan your next flight. Book Tradewind Aviation flights on Alternative Airlines to save big! Alternative Airlines is an online travel agency, specialising in booking lesser-known airlines and remote destinations.