Andy Schell, Mia Karlsson and Ryan Ellison sat around the dining room table, talking about the life of a professional sailor.
They laughed about their adventures, their races and cross-Atlantic cruises. They shared stories about the sailors they know, many tied to Annapolis.
There’s Gary Jobson, the famed TV sailing commentator; Matt Rutherford, who sailed solo around the world on his first major research voyage; and Tom Harkin, the former U.S. senator from Iowa.
“The sailing community, specifically globally, but also in Annapolis, is very small,” Schell said. “I think that it’s also quite supportive, because there’s so few of us and everybody’s doing the same thing.”
Then there’s Jen Kaye.
If three sailors at the table can talk about the waters off Sweden and France, the fourth will tell you all about the Chesapeake Bay. Kaye will explain boarding 15,000 passengers a season, and hiring a dozen captains and hundreds of crew to run four charter trips a day.
And she can explain an experience so magical that it powered Schooner Woodwind — an improbable business idea launched in 1993 — far beyond anyone’s expectations.
“You know, we’ve become iconic now,” Kaye said. “I think that is hard to replicate.”
Last week, the Kaye family sold its two 74-foot schooners to 59º North Sailing, a rare change in a rarefied field.
This was Kaye’s dream. After a college semester aboard a charter sailboat in New England, she convinced her parents, retired teachers Ken and Ellen Kaye, to give up their summers on Long Island Sound and make sailing a profession.
They scouted the East Coast and decided Annapolis was the right place.
“When we started it, we knew that there wasn’t anybody here doing this,” Kaye said. “There was a boat that was named Begin Again and they had a dry-erase board that said, ‘Free pretzels. You can sail naked.’”
It seemed weird, and not just the sign. There should be easy opportunities to sail in a city that calls itself America’s Sailing Capital, even if that’s just a play on words.
The family commissioned boat builder John Scarano in Albany, New York, to design and build a wood-epoxy, two-masted schooner. Woodwind sailed into Annapolis in June 1993.
Ken Kaye was the first captain, and Ellen Kaye soon moved from crew to operations on shore. Jen Kaye landed on both sides of the business.
By 1998, Schooner Woodwind had grown enough that the Kayes commissioned a second boat from Scarano, Woodwind II. At first, the expansion was bumpy.
In a promotional match race with dozens of people from the regional hospitality sector aboard, the schooners tangled in the Severn River and a forestay was torn away.
No one was injured and the boats were both back on the water in two days. Still, it was a frightening, embarrassing moment that could have been far worse.
Jen Kaye is still flustered by the memory, calling that summer the one with a “stubby boat.” Ken Kaye, now eight years past his last voyage as a captain, is more prosaic.
“I’m very competitive,” he said. “It was my fault.”
If one boat was lovely, two created a vision instantly recognizable. Tall, graceful silhouettes, gliding singly or in tandem across Annapolis Harbor.
The City Dock berth at Annapolis Waterfront Hotel — the hotel has changed names and owners four times since the schooners arrived — is a key to its success.
The schooners are so much a singular sight that they landed a role in “Wedding Crashers,” the 2005 comedy shot on the Chesapeake and the Eastern Shore.
Schell saw them while sailing the bay from Rock Hall, where his family kept a boat. In 2006, he needed a college internship and wrote the Kayes.
He convinced them to let him shadow Jen on land and water, even though they didn’t have an internship program.
“I think the No. 1 takeaway for me was that Jen was so good at marketing,” Schell said. “Marketing and enthusiasm, and how important that is, to creating a brand and a culture.”
It carried over. In 2015, he and Karlsson formed 59° North in Sweden with investors. They operate a boat in Norway and another from ports around the world, charging passengers to experience offshore sailing as crews aboard a high-performance boat.
“This would not work if you don’t have the passion,” Karlsson said. “Me and Anders are still out sailing.”
Jen Kaye made the trip in 2023, after reconnecting with Schell. They’d already started talking about the idea of a sale.
Standing at the stern of Woodwind II on Thursday, opening day of the Annapolis Sailboat Show, the new and old owners talked about what comes next.
“Part of our whole thing of starting this business was to make people feel like they were sailing with family,” Kaye said. “And our crew members have become part of the family. This is a prime example of a new family taking over.”
The sale (terms weren’t disclosed) will loosely connect the two ventures. Selling Schooner Woodwind will remain the focus in Annapolis, but now it will market sailing beyond the bay to the daring. 59º North’s boats will remain overseas.
Ellison will take on Kaye’s role, and she’ll stay on through May as a consultant. They’ll sail Woodwind II next week in the Great Chesapeake Bay Schooner Race between Baltimore and Norfolk.
“This was just perfect timing for getting involved and having such a great business that’s iconic in the area,” said Ellison, who moved to Annapolis last year. “I know the questions come up a lot, because it was a family business. This is a family business corporation.”
Sail competitors have come and gone. The Annapolis Maritime Museum sails its restored skipjack, Wilma Lee. There are a few catamarans. There are plenty of powerboat options.
The fact that there’s nothing else like Schooner Woodwind is a testament to how difficult running a commercial sailboat can be.
“Sailing is magic,” Ken Kaye said. “Not making meatloaf.”
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