Why Tradewind Aviation’s David Zipkin Is Betting Big on Bougie Weekenders

David Zipkin, co-founder and chief commercial officer of Tradewind Aviation, isn’t peddling mere airline seats—he’s selling time. It’s a commodity his affluent clientele prizes above all else, especially when it means sidestepping the usual travel tribulations that plague weekend escapists. In an era where major carriers struggle with efficiency, Tradewind’s approach is a breath of fresh air at 10,000 feet. This seamless journey isn’t just a perk of Zipkin’s position—it’s the core product he and his brother, Eric, have honed since 2001. While legacy airlines tout an extra inch of legroom as innovation, the Zipkins have spent two decades rewriting the playbook on regional air travel, one plush flight at a time.

Tradewind Aviation sprouted from a deceptively simple concept: what if jetting to your weekend haunts could be as enjoyable as the destinations themselves? “We started by addressing the gap in availability and quality of service on short-range flights,” Zipkin tells Observer. “The traditional airline experience on short flights has the traveler spending more time in the airport than in the air, and traditional private jets are expensive and inefficient. We solve this problem by flying modern turbine-powered Pilatus PC12 aircraft that are much more efficient, with no compromise in the flight experience and safety.” 

This model has allowed Tradewind to carve out a lucrative niche in the cutthroat Northeast corridor, whisking the well-heeled to and from enclaves like Nantucket and Martha’s Vineyard. What sets Tradewind apart in the private charter world is its focus on efficiency and cost-effectiveness for shorter distances. “Within the market for shorter distance private charter, Tradewind operates the largest fleet of dedicated on-demand Pilatus PC12 aircraft,” Zipkin notes.

While the term “better than first class” is often bandied about in aviation, Tradewind’s offering genuinely surpasses the traditional premium experience. The Pilatus PC-12’s cabin, though more intimate than a commercial airliner fitting up to 10 passengers, offers a level of comfort that rivals or exceeds first-class accommodations on most domestic flights. Plush leather seats with ample legroom, large windows for panoramic views and a whisper-quiet cabin create an atmosphere of refined luxury, though they’re best suited for quicker jaunts rather than cross-country red-eyes or international travel. You may still want the lie-flat seats for those. 

But it’s not just about the in-flight experience. “The major advantages are in the arrival, pre-flight and boarding process,” Zipkin explains. “In the U.S., Tradewind operates from private jet terminals, allowing our guests to arrive just 30 minutes before departure.” This means no long security lines, no crowded terminals and no fighting for overhead bin space. “When the flight is ready to board, our guests are walked out directly to the plane,” he adds. It’s a level of convenience and personalization that even the most premium commercial services struggle to match.

But Zipkin’s ambitions stretch beyond the Hamptons set. “Our next move was to allow our guests to share a charter aircraft, offering scheduled service with the same conveniences of a private charter,” he explains. This hybrid approach has been particularly transformative in the Caribbean, where island-hopping can be a logistical nightmare. “In December, we will launch new service to Marsh Harbour and North Eleuthera in the Bahamas from West Palm Beach,” he reveals. It’s a strategic play tapping into the surging demand for hassle-free tropical getaways, especially as winter’s chill sets in.

Tradewind’s success is built on its ability to adapt with the seasons. As autumn leaf-peepers trade places with sun-seeking snowbirds, the airline nimbly shifts its focus. “We are always looking for new opportunities where we can add significant value to travelers,” Zipkin says. “Typically, those routes are either underserved or poorly served by the airlines.” When asked about future expansion, he hints at potential new services to East Hampton, Montauk, Aspen, and additional Bahamian destinations. “We don’t specifically seek out our personal favorite destinations, but it ends up being that way because some of the best places to go are more difficult to reach.”

While competitors like JSX, XO and Blade operate in a similar space, Tradewind sets itself apart through its unique approach. “We focus on shorter routes and otherwise hard-to-reach destinations, operating out of private jet terminals to create the convenience of a private charter for the cost of a single seat,” Zipkin explains. This strategy translates into tangible benefits for passengers. In the U.S., guests can arrive just 30 minutes before departure at private jet terminals, with valet parking offered at Westchester and Teterboro. Boarding is a breeze: passengers are escorted directly to the plane, bypassing TSA hassles.

The Caribbean experience is equally elevated, featuring a private lounge, VIP transfers and expedited security. “In San Juan, we offer the only airline-specific private lounge and a faster boarding experience with expedited security,” Zipkin notes. While current lounge amenities include complimentary refreshments, he teases future enhancements: “We have more curated experiences in the works, including partnerships to provide unique tasting experiences in our lounges and travel amenities.”

Pricing reflects Tradewind’s commitment to accessible luxury. Caribbean island-hopping on scheduled flights starts at $300, while a seat on a scheduled flights from Westchester to Nantucket begins at $395. (Travelers may also charter a Tradewind private plane at their time of choice, for a higher fee.) For frequent flyers, the Goodspeed Card Program sweetens the deal with block time discounts of up to 30 percent—for example, the Goodspeed 10 card level gives members 10 hours of fly time for $5,190, which comes to approximately $519 per hour.

Staying ahead in the fast-evolving aviation landscape requires constant innovation, and Tradewind is taking steps to address the elephant in the sky: sustainability. While private and scheduled flights inherently carry an environmental cost, Zipkin is steering the company toward a greener horizon. Tradewind recently inked a deal for 20 new Pilatus PC12 NGX aircraft, which Zipkin says will “offer improved fuel efficiency and additional comfort.” But efficiency is just the beginning. “We’re not naive about our industry’s environmental impact,” Zipkin admits. “That’s why we currently purchase carbon offsets for all flying. It’s not a perfect solution, but it’s a start.” He’s also eyeing the future of aviation fuel. “The Pilatus is capable of operating on sustainable aviation fuel, which we will begin to use as it becomes more available,” he explains. 

Perhaps Tradewind’s most ingenious move is its approach to the industry-wide pilot shortage. “We have established strategic partnerships with major airlines to offer a gateway program for pilots to fly with Tradewind and then move on to the airlines,” Zipkin says. “These partnerships help us with both sourcing and retention of high-quality pilots and provide them with an attractive pathway to flying with the airlines.” Zipkin acknowledges the paradox of promoting sustainability in an inherently carbon-intensive industry. By focusing on shorter routes and using more efficient aircraft, Tradewind may actually help reduce the overall carbon footprint compared to larger jets or multiple commercial flights. It’s a nuanced approach to a complex problem, balancing the demands of discerning travelers with the pressing need for environmental responsibility.

As the aviation industry continues to navigate post-pandemic headwinds, Tradewind’s premium-focused model seems to be gaining altitude. The company has identified a sweet spot in the market: offering a service that outshines commercial first class while remaining significantly more affordable than full private jet charters. To put this in perspective, traditional private jet charters can range from $1,200 per hour for a turboprop to a staggering $8,000 per hour for larger aircraft. In contrast, Tradewind’s approach makes luxury air travel more accessible with single-seat and membership purchases at a fraction of what a full private charter might cost. 

While major carriers focus on rebuilding their core businesses, Tradewind’s nimble strategy could position it for continued ascent. “We’re not trying to be everything to everyone,” Zipkin reflects. “We’re focused on providing an unparalleled experience for travelers who value their time and comfort above all else.” With its blend of luxury, efficiency and a nod towards sustainability, this family-owned upstart is proving that in the dog-eat-dog world of aviation, sometimes flying under the radar is the most direct route to success. As Tradewind continues to expand its routes and refine its services, it may well be charting the course for the future of premium air travel.