Search & Book Tradewind Aviation Flights

Cabin class:



Search by country, city or airport

Select a departure date

Search flights
Feefo Reviews
payments accepted
IATA Accredited

Book Tradewind Aviation Flights

Book Direct with Tradewind Aviation and Alternative Airlines

An American airline, Tradewind Aviation, is 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. In the Caribbean destinations include San Juan, Saint Barthelemy, West Indies, Anguila and United States Virgin Islands. Tradewind Aviation was founded in 2001 on the premise that every flight deserves the highest quality aircraft, crew and service.


In October 2016, Tradewind Aviation 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 will facilitate connections to many airlines in the US and beyond, making it easier than ever to get to this vacation hotspot. Passengers traveling 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.


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. 


In 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.

In 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. 




Book Flights with Tradewind Aviation

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. 

Find Out More

How to pay

You can pay for your flights with Tradewind Aviation in the currency and payment method of your choice when booking through Alternative Airlines.

We accept PayPal making flight purchases with Tradewind Aviation easy and more secure for customers. PayPal is one of the leading forms of online payment, with more than 169 million accounts worldwide.

How to pay with PayPal