Singles on Sailboats offers sailing opportunities, training, and friendships.
Maybe you’re single, and you bought a sailboat only to discover family and friends think a couple of days a season is enough. Or maybe you’ve lost your sailing spouse. Perhaps you’re boatless, but your pals with boats are couples, so you feel like a fifth-wheel. Those scenarios led to the launch of Singles on Sailboats (SOS) 47 years ago.
“It’s not a dating club, but a social sailing club where people can share learning and good times and make great friends,” says Victoria Rusakova of Bethesda. (That’s not to say Cupid doesn’t connect those who share a passion for sailing; members who marry can—and do—remain in the club).
Victoria found her way to the SOS Rockville happy hour in late summer 2024. “I was absolutely blown away as to how friendly and accessible people were,” she says. “Everyone told me something positive about the club and connected me with people. They wanted to ensure that I got in on the last sails of the season.”
Membership at $80 yearly means many affordable opportunities to sail as well as socialize, drawing folks from a wide area including Pennsylvania and Delaware. Crew fees range from $20 for a daysail to more for overnights and catered dinners onshore. SOS volunteers work with a dozen committees including cruising, social, and education to make it all happen. Folks typically look into SOS in mid-life when family and career give them some breathing room, but all ages are welcome.

For those new to sailing, “Dockside Training” includes stepping aboard a docked vessel for an introduction. All new members engage in a “Basic Skills” program to review and put into practice everything from rules of the road to man overboard drills. More seasoned crew can join the “First Mate” program to keep their know-how sharp while assisting skippers.
For some 30 daysails and 20 cruises each season, skippers set sail from the Annapolis area, Baltimore, and as far south as Deale and Solomons. You might find yourself at the helm of a monohull or zooming down the Bay on a trimaran. Some cruises aim for marinas, with dinner and dancing to a DJ. Others culminate in raftups at tranquil anchorages. SOSers have also enjoyed bareboat cruises at destinations including Lake Champlain, Croatia, and New Zealand.
Dozens of skippers volunteer their time, skills, and boats. What’s in it for them? Chuck Fort of Newark, DE, met his wife Julie in the club; they sail their Hunter 42 At Last out of Kent Island. He highlights “the chance to have experienced crew every weekend and the chance to teach novices so that you have more good crew in the future.”
Newer member Josh Graff of Baltimore found that “SOS is the cheapest way to sail, period. On top of that, you’re sailing with people with a lot of diverse interests and experience, both in sailing and in life.” Chuck is a great mentor, he says, and “I learn from everyone I talk to. Not only sail trim and proper handling and technique, but also what it means to be aboard safely and be a good cruiser. SOS people have been doing it for 10, 20, 40 years and more.” Josh gained confidence in the club and now owns a Freedom 30.
Safety is built into the SOS experience. Boats must have appropriate equipment aboard. “Every SOS cruise starts with review of a safety checklist,” Josh points out.

At “Flare and Safety Day” participants get plenty of hands-on practice setting off fire extinguishers, using a winch while protecting fingers, and tossing lines accurately. A raft seminar informs skippers and crew so that raft-ups proceed as smoothly and safely as possible—no small task when larger numbers of boats are involved.
All this learning together, not to mention glorious days sailing the Chesapeake, builds a wonderful sense of camaraderie mentioned by just about everyone you talk to. Bev Nash of Annapolis, who cherishes SOS friendships dating back 44 years, helps organize some of the events that keep members connected in the off-season, which include small “fireside chat” dinners, regional holiday pot-lucks, and monthly brunches in Annapolis with guest speakers.
“I love SOS because you can get out of it what you want,” says Bev. “There are people you will see all summer long who sail every cruise they can but never go to social activities. There are those who do some sailing, some social stuff.” As the club T-shirt says, “Come for the sail, stay for the friendship.”
SOS happy hours take place monthly: Philadelphia Area (Media, PA); Wilmington, DE; DC/Northern VA(McLean); and Rockville, Baltimore, Ellicott City, Kent Island, and Annapolis, MD. Find more at singlesonsailboats.org.
by Catherine Fox