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Scheduled Service Flights to Anguilla, the British Virgin Islands, and the Bahamas Now Booking!
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    AIRPORT INFO & TRAVEL REQUIREMENTS

    • Anguilla
    • Antigua
    • Marsh Harbour
    • Martha’s Vineyard
    • Nantucket
    • North Eleuthera
    • Palm Beach
    • San Juan
    • St Barths
    • St Thomas
    • Teterboro
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Tradewind - Fly Personal

THE TRADEWIND DIFFERENCE
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Providing personal air travel throughout North America and the Caribbean.

PRIVATE

Travel on your schedule and to any destination throughout North America and the Caribbean.

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SCHEDULED

Offering the comfort and convenience of private service for the cost of a single seat.

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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.

Experience

Incredible Destinations

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.

St Barths
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Virgin Gorda beach and resort
Virgin Gorda
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View of Ocean Cliffs in Marthas Vineyard
Martha's Vineyard
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Palm Beach
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Newport
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Anguilla
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Nantucket
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Marsh Harbour
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Stowe
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Antigua
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Explore all destinations

In the news

"Top 5 Airline in the U.S. in 2021, 2022, 2023, and 2024 -Conde Nast Traveler Reader's Choice Awards"
"The best way to travel to Nantucket and Martha's Vineyard is on Tradewind Aviation, a U.S.-based operator providing private charter service and shuttle flights along the Northeast and Caribbean."
"The dramatic arrival via Tradewind Aviation on one of the smallest runways in the world is something you will remember forever."
"Getting to ACK—[Nantucket’s] airport code—has never been easier with Nantucket shuttles from Tradewind Aviation that are as close as you’ll come to flying private on commercial aviation."
"For a seamless - and fast (read: no traffic) - trip to Martha's Vineyard from the New York area, book a flight on Tradewind Aviation."
"Reaching the small, dreamy island of Anguilla is quick and easy thanks for intra-Caribbean luxury carrier, Tradewind Aviation."

Partner Experiences

Rosewood Little Dix Bay in Virgin Gorda, The British Islands
Rosewood Little Dix Bay

Guests who fly Tradewind scheduled service to Virgin Gorda and stay 3+ nights at Rosewood Little Dix Bay will receive complimentary VIP Experience for their transfer in San Juan ($250 value), while private charter guests receive a 5% discount. Once at Rosewood Little Dix Bay, guests receive between $150-$400 resort credit based on the booking room category.

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Necker Island
Necker Island

Fly Tradewind scheduled service from San Juan to the British Virgin Islands and receive complimentary VIP Experience at the San Juan Airport for a seamless transfer to your Tradewind flight. Or, book a private charter with Tradewind to the BVI 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.

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Exclusive Resorts

Experience the vacation of a lifetime, every time. Exclusive Resorts is a members-only club designed for families with a private portfolio of luxury residences and rare experiences. A special offer to Tradewind Goodspeed Card Members and Ticket Book Holders, become an Exclusive Resorts Member and receive $20,000 off your initiation fee.

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Cap Juluca, a Belmond Hotel

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 10% discount on their hotel accommodation.

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Zemi Beach House
Zemi Beach House

Guests who fly Tradewind scheduled service to Anguilla and stay 3+ nights at Zemi Beach House will receive complimentary VIP Experience for transfers in San Juan, or a 5% discount on scheduled flights from Antigua or St Barths. Private charter guests receive a 5% discount on their air travel. Once at Zemi Beach House, receive between $150-600 daily hotel credit and a welcome amenity.

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Casa de Campo

Exclusive for Goodspeed Card Members, fly to La Romana with Tradewind and stay at Casa de Campo Resort & Villas to receive a $500 resort credit per stay, 5% off any Exclusive or Ocean Front Villa category, complimentary airport pickup and return from the airport, private VIP services, and welcome amenities.

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The Cove Eleuthera

Guests who fly Tradewind to North Eleuthera and stay at The Cove will receive a resort credit to use during their stay on food, beverage, spa, or property activities.

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Altamer Luxury Villas

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 Island Explorer Package, or a standard discount off your stay.

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Nevaeh Villa Anguilla

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.

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Faraway Hotels

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.

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The Chatham Bars Inn

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.

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Fairmont El San Juan Hotel

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.

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Quintessence Hotel

The Champagne, Caviar, and Chocolates package offers one of the most private and most exclusive experience in Anguilla.

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Le Sereno

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.

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Hotel Le Toiny

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.

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Newport Jaguar Tours

Experience Newport’s rich history, architecture, art galleries, and more with Newport Jaguar Tours. Tradewind guests receive an exclusive 10% discount on a private guided tour through Newport’s picturesque streets in classic Jaguar motorcars.

Newport Jaguar Tours
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Discover all partner experiences
TW Store

Now Landing: The Tradewind Store!

Explore our collection of Tradewind gear — hats, sweatshirts, t-shirts, bags, and more. Whether for yourself, friends, or family, you can now showcase what it means to ‘fly personal’ with our new merch!
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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.

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      By entering my mobile number and checking “Receive important messages via SMS” I agree to opt in to receive important messages from Tradewind Aviation regarding enrollment, renewals, event and general information about our services. Messaging frequency varies. Text HELP to 97174 for help, Text STOP to 97174 to end. Msg&Data Rates May Apply. By opting in, I authorize Tradewind Aviation to deliver SMS messages using an automatic telephone dialing system and I understand that I am not required to opt in as a condition of purchasing any property, goods, or services. By leaving this box unchecked you will not be opted in for SMS messages at this time. Click to read Terms and Conditions, Privacy Policy.

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