Providing personal air travel throughout North America and the Caribbean.
Travel on your schedule and to any destination throughout North America and the Caribbean.
Offering the comfort and convenience of private service for the cost of a single seat.
The Tradewind Difference
Tradewind was founded on the premise that every flight deserves the highest quality crew, aircraft, and service. Learn more about how Tradewind is elevating the standard for air travel.
Enjoy seamless scheduled and private travel to some of the more luxurious destinations throughout North America, the Caribbean, and beyond. Discover our most popular destinations and the most convenient ways to get there.
In the news
Journey to the paradise of the BVI with Tradewind Aviation to experience Necker Island, Sir Richard Branson’s 74-acre private island.
Fly Tradewind scheduled service from San Juan to Virgin Gorda and receive complimentary VIP Experience in San Juan. Or, book a private charter with Tradewind to Virgin Gorda to receive a 5% discount on your airfare.
Stay at Necker Island during an Exclusive Use booking to receive an additional night of complimentary entertainment. Or stay at Necker Island during an Individual Stay to receive $100 credit to be applied to the spa or gift shop.
Guests who fly Tradewind scheduled service to Anguilla and stay at Cap Juluca, a Belmond Hotel, will enjoy complimentary VIP Experience for their transfer in San Juan, while scheduled service transfers through Antigua and St Barths enjoy a 5% discount. Tradewind private charter guests will receive a 5% discount on their travel. Once at Cap Juluca, Tradewind guests will enjoy an exclusive discount on their hotel accommodation.
Guests who fly Tradewind to Anguilla and stay 5 nights or more at Malliouhana receive this offer. Fly Tradewind scheduled service from San Juan to enjoy complimentary VIP Experience in the San Juan Airport, or fly scheduled service through Antigua or St Barths to enjoy a 5% discount. Tradewind private charter guests will receive a 5% discount on their travel. Once at Malliouhana, receive 20% off the best available rate and a $250 resort credit.
Unwind on Anguilla’s Shoal Bay West with this offer from Tradewind and Altamer Luxury Villas. Receive a 5% discount on your round-trip private charter, as well as personalize your stay at Altamer by choosing amenities from either the Island Bliss Package or the Island Explorer Package.
Guests who fly Tradewind scheduled service to Anguilla and stay at Nevaeh Villa Anguilla will enjoy complimentary VIP Experience for their transfer in San Juan or a 5% discount for transfers from Antigua or St Barths. Tradewind private charter guests will receive a 5% discount on their travel. Once at Nevaeh, Tradewind guests will enjoy a complimentary welcome barbecue dinner serenaded by a guitarist.
The Romance Package at Fairmont El San Juan Hotel includes everything couples need for a romantic weekend to set the stage for an unforgettable proposal.
Visitors who book this offer and stay at Le Sereno will enjoy a complimentary 45 minute massage at Valmont Spa and an in-room amenity kit containing a beach bag and bottle of champagne.
Visitors who book this experience and check into a luxury one bedroom suite at Hotel Le Toiny will enjoy a private pool, VIP amenities including full daily breakfast, access to a full mini bar, and a special bottle of champagne.
Guests who book this package will receive a 5% discount on their private charter, and between 10-15% off their accommodation depending on booking dates.
Discover Nantucket’s wild side with an off-season visit to Greydon House. Book a private charter to Nantucket with Tradewind to enjoy 10% off your flight and 15% off three-night or more stays at the Roman and Williams-designed hotel.
Fly private with Tradewind to the Chatham Bars Inn for a night of luxury. At Chatham Airport, enjoy a complimentary Lexus shuttle stocked with chilled champagne to the Inn, then bypass check-in and be escorted directly to your room or suite.
We’d love to hear from you. Please fill out the contact form and our team will be in touch to discuss your travel needs.