The company is also celebrating its landmark year with a new scheduled service to Newport, Rhode Island, and Anguilla.

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Tradewind Aviation is celebrating its 20th anniversary in a big way. The regional flight company will give away one round-trip private charter flight — worth $20,000 — to reunite a family separated during the pandemic.

After all, family has been the backbone of the company since it was founded by brothers Eric and David Zipkin in 2001 — and it has remained a family-owned and operated business throughout the last two decades. Tradewind will reveal the details for its 20th anniversary giveaway on its Instagram page in October.

CJ3 private plane Interior
Credit: Chad Slattery/Courtesy of Tradewind Aviation

In addition to the sweepstakes, the company is celebrating its landmark year with a new scheduled service to Newport, Rhode Island, as well as with the return of its popular service to Anguilla this coming winter, the company said in a release.

The company has long been at the forefront of the shared charter concept ever since it launched scheduled services between the private terminals in New York's Westchester County Airport, New Jersey's Teterboro Airport, and Massachusetts' Nantucket Memorial Airport in 2002. Service was soon added to Massachusetts' Martha's Vineyard Airport and Vermont's Morrisville-Stowe State Airport. Tradewind also operates scheduled service in the Caribbean from San Juan, Puerto Rico, to Anguilla and St. Barts, as well as from St. Barts to St. Thomas and Antigua.

CJ3 private plane in Flight
Credit: Jessica Ambats/Courtesy of Tradewind Aviation

With a fleet of top-of-the-line aircraft, including 18 Pilatus PC-12s and three Citation CJ3 jets, Tradewind plans to add two new Pilatus PC-12 NG planes this fall. The company also started offering the Goodspeed Card program in 2018 with 18% off private charter flights, as well as a carbon offset program in 2020 by contributing to its partner, TerraPass.

"For 20 years, our family-owned business has provided travelers an efficient and cost-effective way to access anywhere, from major cities to top leisure destinations throughout North America and the Caribbean, saving hours on road travel," Tradewind's cofounder and vice president, David Zipkin, said in a statement. "With preboarding lounge access, priority security, and a swift onboarding and deplaning experience, passengers can travel comfortably and efficiently at very competitive fares. We're excited to celebrate our 20 years in business with this incredible giveaway."