Tradewind Aviation News & Press

- June 1, 2026 - Miami Living Tradewind Aviation is tapping into one of the Caribbean’s most distinctive seasonal celebrations with the launch of its first-ever “Christmas in July” flights to Virgin Gorda. The limited-time service will operate from San Juan, Puerto Rico (SJU) from July 19–26, 2026, marking the first time the airline has programmed dedicated lift timed to the island's annual mid-summer celebration.

- May 26, 2026 - Travel Weekly Tradewind Aviation is launching its inaugural "Christmas in July" flight service to Virgin Gorda, tapping into one of the Caribbean's most vibrant mid-summer traditions.

- May 9, 2026 - Caribbean Journal Tradewind operates flights to St Barths from San Juan, with travelers boarding Tradewind’s Pilatus PC-12 aircraft for the final leg into Gustaf III Airport. The experience is far more private and refined than a standard regional airline connection, with dedicated lounges, streamlined boarding, high-end snacks and beverages, and impeccable service. San Juan also has more flights than just about anywhere from the US.

- May 1, 2026 - Caribbean Journal Getting to St Barths is part of the experience, and the route you choose shapes the tone of the trip before you even arrive. The most seamless option is flying Tradewind Aviation from San Juan, which remains the best way to get to the island, and it isn’t really close. From the moment you arrive in San Juan and head up to the airline’s private VIP lounge, it’s almost like you’re already on St Barth diplomatic territory.

- April 28, 2026 - Travel Dreams Magazine Launching its first-ever “Christmas in July” flights this year to Virgin Gorda, Tradewind Aviation is tapping into one of the Caribbean’s most distinctive seasonal celebrations. Limited-time service is scheduled to operate from San Juan, Puerto Rico (SJU) from July 19-26, 2026, aligning with the island’s festive mid-summer celebration. This marks the first time Tradewind has programmed dedicated lift timed to the annual event.

- April 28, 2026 - Private Jet Card Comparisons Tradewind Aviation will offer pop-up flights this summer connecting Virgin Gorda with San Juan, Puerto Rico. The scheduled by-the-seat flights will run July 19 through 26, 2026. The flights align with Virgin Gorda’s mid-summer festival.

- April 28, 2026 - The Martha's Vineyard Times Tradewind Aviation, which already operates private chartered flights to the Island, announced in late March that a new scheduled route to and from Boston launches June 18. Travelers can depart from a private terminal at Hanscom Field in Bedford, 14 miles outside of Boston, to Martha’s Vineyard or Nantucket on three daily departures.

- April 24, 2026 - Modern Luxury Part of what kept the BVI feeling exclusive was how hard it could be to reach. New regional options through expanded Tradewind Aviation service from San Juan are filling in the gaps, making spontaneous trips feel far more realistic.

- April 15, 2026 - Oprah Daily Tradewind Aviation, a private air service that operates throughout North America and the Caribbean, would fly our group the short distance from Florida to the Bahamas. The flight was an easy hour into Eleuthera; we breezed through customs in under ten minutes, and were soon on our way to The Cove via the property’s private van.