Luxury Airline Tradewind Aviation Expands Scheduled Flights to the Caribbean

Luxury airline Tradewind Aviation has announced the launch of new scheduled flights to key vacation destinations across the Caribbean, giving passengers more chances to island hop in style this winter.

Tradewind Aviation, founded in 2001 by Eric and David Zipkin, is an award-winning private aviation provider offering shared charter flights to sought-after leisure destinations.

The private airline initially offered scheduled flights across the Northeastern U.S., but it quickly expanded to the Caribbean, and it’s now set to strengthen its presence there further this upcoming winter season.

Photo: Courtesy of Tradewind Aviation

Starting on November 21, Tradewind will launch a scheduled service from in San Juan, Puerto Rico (SJU), to the island of Tortola in the British Virgin Islands (BVI). Tortola is the largest of BVI’s islands, offering a diverse range of attractions for travelers, from luxury resorts and lively townships to ancient ruins and pristine beaches. The flights will run from Thursdays to Mondays until April 21, 2025, and start at just $179 one way.

Also, on November 21, Tradewind will launch seasonal flights from San Juan to Virgin Gorda (VIJ). Also in the British Virgin Islands, Virgin Gorda is smaller than Tortola and arguably even more idyllic. Filled with exclusive villas and high-class restaurants, it also features the Baths—one of the most picturesque spots in the Caribbean. Flights will run until April 21, 2025, and start at $143 one way.

Photo: Anguilla, Caribbean. Courtesy of ory Bjork / Unsplash

Finally, on December 19, the airline will launch scheduled flights to the tiny island nation of Anguilla (AXA) from three departure points—Gustaf III Airport (SBH) in St Barths, VC Bird International Airport (ANU) in Antigua, and San Juan. Travelers can expect tranquil white beaches, world-class dining, and an extensive selection of watersports in Anguilla.

Flights from San Juan, starting at a pocket-friendly $355 one way, will operate from Thursdays through to Mondays with the addition of weekly flights during New Year’s week. Meanwhile, flights from St Barths, priced at just $ 115 one way, will operate Thursday to Saturday, and flights from Antigua, starting at $ 200 one way, will operate on Saturdays and Sundays. All services to Anguilla are scheduled to end on April 14, 2025.

Photo: Courtesy of Tradewind Aviation

“We are offering more convenience to destinations that provide the luxury hospitality and vacation experiences our clientele desire,” said David Zipkin, Co-Founder and Chief Commercial Officer at Tradewind Aviation. “We are all working together to boost tourism and cultural exchange in the Caribbean, and we’re looking forward to sharing in the successes.”