The Zipkin Brothers Turned an Empty Seat Into an Airline

In 2001, two brothers with pilot licenses looked at one of the most traveled short routes in America - New York to Nantucket - and saw something the rest of the industry had quietly accepted. The planes were old. Many flew with a single pilot. And the service did not match what people were paying. Eric and David Zipkin decided that a 45-minute hop to an island deserved the same standard as a private jet. That decision became Tradewind Aviation, and more than two decades later it is a fleet of over 30 aircraft that still insists it is a charter company first and an airline second.

Tradewind is headquartered in Oxford, Connecticut, at Waterbury-Oxford Airport, and it occupies a slice of aviation most travelers have never had a name for. It is not a commercial airline in the way that word usually lands - no jet bridges, no boarding groups, no middle seats. It is not quite a private charter either, because you can buy a single seat at a published price. The category has since acquired a label, "semi-private," and Tradewind is one of its clearest working examples.

01 / The OriginAn idea that came from the customer

The company started small and unglamorous, with a single Cessna Caravan and operations that began around 2002 on the Cape and Islands. Eric had spent time working for a charter company, which is where he learned the mechanics of the business and spotted the gap. At the time, getting from New York to Nantucket often meant aging aircraft, inconsistent maintenance, and one person up front. Tradewind's answer was modern planes, two pilots, and a full-service cabin.

The pivot that turned a charter outfit into an airline did not come from a strategy deck. It came from customers. Clients began asking whether they could share a flight - and the seat cost - with someone headed the same way. That request became the scheduled shuttle: publish the route, sell individual seats, and keep the charter-grade service on board. It is a rare case of a business model arriving by demand rather than design.

02 / The ProductOne airplane, chosen on purpose

Almost everything about Tradewind runs through a single aircraft: the Pilatus PC-12, a Swiss-built single-engine turboprop with a pressurized, air-conditioned cabin that seats eight. Betting an entire fleet on one plane type is a deliberate operational choice. Pilots, mechanics, spare parts, and training all standardize around it, which keeps a growing airline manageable. The PC-12 also lands comfortably on the short runways that define Tradewind's map, from island strips in the Northeast to the demanding approach at St. Barths.

The fleet has grown from that first Caravan into more than 30 PC-12s, spanning older models through the current NGX generation, with more on order. In 2022 the company placed an order for 20 PC-12 NGX aircraft in a deal valued at over $100 million - a large commitment for a privately held operator and a signal of how much demand it was seeing for per-seat flying.

03 / The MapAn airline that follows the sun

Tradewind's network is built around seasons, not hubs. In summer, the planes concentrate on the Northeast - Nantucket, Martha's Vineyard, Newport - flying out of Westchester County Airport, with peak Nantucket days running 30 to 40 flights. In winter, capacity shifts south to the Caribbean, where San Juan feeds scheduled service to St. Barths, Anguilla, Antigua, and beyond. More recently the company added Florida-to-Bahamas routes and launched Boston service, extending the same per-seat idea to new corners of the map.

This design is what keeps expensive aircraft busy year-round. A plane parked in October is a cost; a plane that swaps a Nantucket schedule for a St. Barths one is revenue. Following the sun is not a marketing line here - it is the reason the economics work.

04 / The ModelWhere it sits in the market

Tradewind lives in the space between two things travelers already understand. Below it is the commercial airline: cheaper per seat, but with the full weight of terminals, security lines, and connections. Above it is the on-demand charter jet: private and flexible, but priced for the whole aircraft. Semi-private takes the per-seat price from one and the private-terminal experience from the other.

The revenue mix follows from that position. Money comes from scheduled per-seat tickets and discounted ticket books on routes like Nantucket, from on-demand charter hours, from the Goodspeed jet-card membership program launched in 2019, and from managing aircraft on behalf of owners. Notably, Tradewind built this without a splashy public listing or a headline venture round - growth came route by route, largely self-funded, in an industry better known for burning cash.

The customers reflect the map. In summer, the Northeast routes draw families and second-home owners heading to Nantucket, Martha's Vineyard, and Newport, plus business travelers who value a short drive to a private terminal over a long slog through a main airport. In winter, the Caribbean network serves leisure travelers heading to St. Barths and the smaller islands, often as the final leg after a long-haul flight into San Juan. Charter clients and aircraft owners round out the base, using the same fleet and crews on demand. The through-line is a traveler for whom the destination is small, the trip is short, and the airport experience is the part they most want to avoid.

05 / The PeopleTwo brothers, separate lanes

The company is still run by the two people who started it. Eric Zipkin serves as CEO and leads operations; David Zipkin serves as Chief Commercial Officer and runs the commercial side. Both are pilots. Asked how a family business survives two decades intact, their answer is almost anti-collaborative: they trust each other implicitly and mostly stay out of each other's lanes. It is a quiet, practical model for co-founders, and it has held while the fleet multiplied and the payroll grew to roughly 350 people.

The brothers have also pointed the fleet at problems outside the schedule. Tradewind coordinated relief flights after Hurricane Irma and following the 2010 Haiti earthquake, treating the same aircraft that shuttle passengers to the islands as tools for getting help in when it is needed.

06 / The RecordPropeller planes on a best-airlines list

The clearest outside signal of how this plays with travelers is a recurring one. Tradewind has been named among Conde Nast Traveler's best U.S. airlines by its Readers' Choice Awards for five consecutive years, reaching the top five - unusual company for an operator flying eight-seat turboprops out of small terminals. Readers tend to credit the staff and the absence of the usual airport friction rather than lie-flat seats or lounges.

Even the branding is disciplined. Tradewind's radio call sign is GOODSPEED, its ICAO identity is GPD, and its jet-card program carries the same name. For a company that has never leaned on a large advertising budget, the identity does a lot of quiet work: one word, repeated everywhere from the cockpit radio to the membership card.

07 / What's NextThe category is growing up

Semi-private is no longer a curiosity. Competitors like JSX, Wheels Up, Aero, and Blade are all chasing versions of the same promise - skip the worst parts of the airport, pay less than a full charter - and the fact that the category now has named rivals is itself the story. Tradewind's edge is its focus: a single aircraft type, a seasonal map it knows cold, destinations that larger carriers avoid, and a service standard borrowed from charter rather than from coach.

For a traveler, the practical version is simple. If your trip is a short hop to an island the majors underserve, Tradewind lets you buy one seat, walk through a private terminal, and fly with two pilots on a plane built for exactly that route. That is the whole idea the Zipkin brothers spotted in 2001 - and, more than two decades on, it is still the pitch.