Meet Returning Sailor Matthew Sheridan
One never knows where life’s twists and turns will lead. Sometimes, a seemingly unfortunate situation has a silver lining. For Matthew Sheridan, a move from the West Coast to the East Coast to care for an aging parent led to a return to sailing.
Matt learned to sail as a small boy aboard his father’s 12-foot O’Day Widgeon in Lancaster County, PA. Later, during high school, he raced Lightnings on the Susquehanna River. In 2022, after moving from California to Annapolis, Matt, then in his mid-50s, said to himself, “When in Rome…” and jumped back into sailing. Here is some of his story in his own words.
Back to school
When I moved to Annapolis, right out of the gate I was lucky enough to be invited aboard a boat for Wednesday night racing. Immediately I realized three things: 1) I had forgotten a lot during my 30-year hiatus, 2) boat technology had changed, and 3) there was a lot I did not know in the first place.
I dove back in, beginning with the basics. I completed ASA 101, 103, and 104 courses at Annapolis Sailing School, attended a Maryland Safe Boating course, and in 2024 and 2025 participated in American Sailing’s Performance Race Week, held in St. Thomas, US Virgin Islands.
Getting reoriented to what was going on and why on a race boat took some practice. At Performance Race Week, the coaches were exceptional, and the focus was on crew work and tactics. I plan to take the course again in 2027, as the week offers excellent training for the distance racing that I do aboard Cheshire Cat (a 30-foot Stiletto owned and skippered by John Enderle, whom I met at the SpinSheet Crew Party in 2023) and for occasional pinch hitting as crew on class racing boats, such as J/70s.
While racing is exciting, cruising lowers your blood pressure, and in the future I hope to do more long weekend cruising on the Chesapeake and beyond.
Building a community
Annapolis is a wonderful community to live in. We are really fortunate. The Keelboat Club (KBC) at the Annapolis Sailing School is a fun, low-cost way to keep getting out on the water. It is a fun community of people, where I’ve made many friends and connections. Maille Lyons, in particular, has encouraged me (and others) to become involved in sailing in a number of different ways, and because of that, I’ve met all kinds of people in the larger sailing community.
On Monday nights at the KBC I race Rainbows. Experienced and inexperienced sailors are paired as crew for casual competition. This gives new sailors the opportunity to be on the water with other people who have gone through classes at the school or have been instructors there. KBC members also have opportunities to reserve Rainbows and larger boats for cruising.
Giving back
I really enjoy sharing sailing with others, which is one reason why I serve as a first mate and crewmember aboard the skipjack Wilma Lee for sunset and heritage cruises out of the Annapolis Maritime Museum. A fantastic group of 75-80 sailors make up the crew’s roster. Our responsibilities include assisting the captain in getting the boat off the dock, putting the sails up, making certain that the guest passengers are safe and comfortable, lowering the sails, and assisting in docking.
I also serve on the board of directors for the Hospice Cup, an annual charity yacht race (September 19) that supports five nonprofit hospice programs in Maryland and Virginia. I was invited to consider the board by its president, John Richard, who was also a KBC member. As well as helping to raise funds, board members work to ensure that our racers, donors, and friends have a wonderful regatta. Recently, we’ve added more fundraising events throughout the year to benefit those we serve. Being a member of this board has been a very rewarding experience.
Do you own a boat or aspire to own one?
I do not currently own a boat. Perhaps a Hinckley Pilot or a Chris Craft Cherokee are in my future. I like working on boats, but time is a little short for that at the moment, as I am still working full time.
If someone were interested in learning to sail, what would you tell them?
I am a big proponent of safety training. In my experience, the higher you raise the safety threshold, the more fun you will have, and when you bring aboard new people, they too will feel safe, which enables them to also have fun and enjoy the experience. ASA 101 is a great way to get started.
Find more about getting into--or back into--sailing here.
