Fly Personal Across North America and the Caribbean

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, 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.

With this exclusive Member-for-a-Stay offer, Tradewind private charter guests can experience The Abaco Club, a Bahamian private club located on Great Abaco Island, and enjoy full-member access along with exclusive benefits during a stay.

Experience seamless travel to your favorite winter destinations from New York City with Tradewind’s newest partnership with BLADE. Tradewind guests receive preferred rates on helicopter transfers from Manhattan’s West 30th Street Heliport to Westchester County Airport (HPN) in conjunction with a Tradewind itinerary.

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 or a 5% discount for private charter guests. Once at Cap Juluca, Tradewind guests can enjoy an exclusive 10% discount on their hotel accommodation, as well as a complimentary 60-minute Muscular Energy or Imperial Relaxing Massage.

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.

Guests who book a Tradewind private charter to Key West and stay a minimum of 2 nights at Lunara Bay will receive a 5% discount on their air travel. If the trip is on a weekday, guests will receive 15% off on their accommodations, or 10% off on a weekend stay.

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.

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 a choice of one complimentary add-on experience during your stay.

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.

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.

Tradewind guests who stay at Nobnocket Boutique Inn can enjoy complimentary pick-up and drop-off from the Martha’s Vineyard Airport, along with a complimentary glass of wine upon arrival.

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.

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 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.

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.