Tradewind Aviation News & Press

- 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.

- April 14, 2026 - British Virgin Islands Traveller For the first time, Tradewind Aviation is launching dedicated flights to Virgin Gorda timed specifically for the island’s beloved mid-summer celebration. Operating from San Juan between July 19–26, 2026, this limited-time service is designed to bring travelers straight into the heart of one of the Caribbean’s most distinctive events.

- April 14, 2026 - Caribbean Journal Luxury airline Tradewind Aviation is launching its first-ever dedicated “Christmas in July” flights to Virgin Gorda, with limited-time service running from July 19 through July 26. The flights will operate out of Luis Muñoz Marín International Airport in San Juan, Puerto Rico, aligning directly with the island’s week-long celebration.

- April 10, 2026 - Condé Nast Traveler Booking directly with an operator—companies that own, manage, and charter their own aircraft—is ideal for those who prioritize consistency over personalization. Regional operators based at certain airports, like Tradewind Aviation, will typically price best for shorter round-trips out of their base or nearby.

- March 31, 2026 - Undiscovered America Tradewind Aviation has announced a significant expansion of its Northeast scheduled shuttle service, adding direct flights from Hanscom Field (BED) in Bedford, Massachusetts, to both Nantucket (ACK) and Martha’s Vineyard (MVY). The new routes launch on June 18, 2026, turning what can easily become a half-day travel ordeal into a 30-minute flight.