It’s an Annapolis tradition. Almost every day, visitors set sail on the Schooner Woodwind (or Woodwind II) to see the capital city from the most scenic possible vantage point.
From mid-April through Halloween, the twin 74-foot, two-masted staysail schooners wow tourists and locals with their beautiful lines and their 1,800 square feet of sail each. The experience makes seeing Annapolis by water even more special for thousands of visitors. Woodwind Sailing Cruises runs up to four cruises per day in high season.
The tradition has just begun a new chapter as its longtime owners sell the business to a group of friends—who happen to be celebrities in the sailing world. It marks the first change in ownership since Woodwind Sailing Cruises was founded in 1993. Ellen & Ken Kaye, who ran the business with their daughter Captain Jen Kaye, have decided to retire.
The Kayes are selling the operation to sailing entrepreneur Andy Schell and 59º North Sailing, an offshore sailing academy/ adventure cruise business Schell founded with his wife Mia Karlsson. Ryan Ellison, an Annapolis-based sailor known for the popular YouTube channel Ryan & Sophie Sailing, is also part of the ownership group. Ellison will manage day-to-day operations, with Captain Jen sticking around through next spring to help with the transition.
We had the chance to sit down with Schell, Karlsson, Ellison, and Jen Kaye aboard Woodwind at the Annapolis Sailboat Show right after the deal was announced. The new owners tell us they’ll keep the family feel of the business and they are looking forward to diving into the Annapolis community.
There is plenty of Annapolis sailing synergy in this passing of the torch. Schell grew up in Pennsylvania, but his family kept boats in Rock Hall. He was an intern for Woodwind Sailing Cruises as a student and later worked as a deckhand on the Woodwind. He says he learned about running a small business from the Kayes. Karlsson calls Woodwind Sailing Cruises a model for 59º North Sailing. “The Kayes encouraged and supported my dreams of offshore sailing, and it’s in large part thanks to them that 59º North exists today,” he says. “That it’s come full circle now, with a chance for Mia and me to take over as the new owners, is very exciting.”
Ellison says he and wife Sophie have enjoyed putting down roots in Annapolis after several years living aboard and traveling the globe. “It’s hard to have that network, that feeling of home, when sailing around the world,” he tells us. We first met Ryan & Sophie Sailing when they brought their boat to the Chesapeake in 2022. Ellison is now here to stay, managing the business side of Woodwind Sailing Cruises.
With fresh new ownership by influential sailing leaders, we wondered: What changes will passengers on the Woodwind vessels notice? Ellison tells us with a smile, “I hope they don’t notice anything! We didn’t buy this business to make it better, we just want to keep it going.” He says, “While Andy and I have ideas for growth, at its core the Woodwind will remain the same—the same spirit and the same commitment to Annapolis.”
The Kayes are glad to see their legacy continue. “Approaching our eighth decade on this planet, it is time to fully retire from the Schooner Woodwind business and pass it on to a dedicated buyer, like Andy and his team,” say founders Ellen & Ken Kaye. “Thirty years ago, if you’d asked us what would happen to the Woodwind in 2025, we wouldn’t have had an answer, but we’re proud of our accomplishments. What we do know is why we started it—to share the magic of sailing. Andy and Mia understand that, and they’ve been spreading that magic all over the world. We couldn’t have found a better team to carry the Schooner Woodwind forward.”
Jen Kaye is confident that Schell is the right fit. She and Schell reminisce about an offshore excursion Jen took aboard 59º North two winters ago, which took her out of her comfort zone. “It came full circle on Falken (59º North’s Farr 65 ocean-going sailboat),” Schell says. “Jen was the apprentice, not the mentor.”
Jen saw promise in Schell on that trip, too. “Having seen Andy’s leadership firsthand—especially during our Atlantic crossing two winters ago when he skippered Falken—I know his energy and passion are contagious.”
Karlsson, Ellison, and Schell look forward to telling their 59º North Sailing family about Woodwind, and vice versa. “Deckhands and captains [for Woodwind] could get on their own career path with 59º North,” Schell says. Karlsson points out that Woodwind cruises are a great way for 59º North clients to introduce their families to sailing at a more approachable level. And Ellison say people who fall in love with sailing on the Woodwind could have the opportunity to expand their experience with 59º North. “The adventure doesn’t have to stop after a two-hour cruise,” he says.
Woodwind’s last sails for this season are scheduled for Oct. 31. Check out their schedule here.
