Singles on Sailboats Invites You to Come for the Sail, Stay for the Friendship

Hearing the name of local club Singles on Sailboats—especially around Valentine’s Day—likely sparks images of soulmates meeting for the first time on the deck of a yacht.

What you may envision as a niche dating group—a la, but “Chesapeake Bay style”—is not a dating group at all.

This Annapolis-based club is for single adults who want first to sail and second to socialize with others who enjoy sailing. The club holds events in other states such as New Jersey, Pennsylvania, and Delaware to give members living elsewhere a chance to connect.

“Come for the sail—stay for the friendship is our new tagline,” says Janet Gonski, member and former club Commodore. 

The non-profit club—which started back in 1978—counts close to 500 members.

The club makes it possible for singles to find crews and boats—and destinations. “This year, we will have two bareboat trips,” Gonski says. “We will be taking a bareboat trip to the Bahamas in a few weeks. We sail the Caribbean in the winter and the Mediterranean or Europe in the fall.”

 A bareboat charter or trip is an arrangement for the chartering or hiring of a ship or boat where no crew or provisions are included. The individual—or club—renting the vessel is responsible for providing crew and provisions.

“Past bareboat trips include sailing excursions in Croatia, Greece, the British Virgin Islands, the Grenadines, the Windward Islands and Antigua,” Gonski says. 

Members pick a trip that appeals to them and then sign up.

“My favorite experiences have been on the bareboat charters,” says Michael Sommer, a four-year member. “These charters have been a great opportunity for me to sail around the world—something that I would never have been able to do alone without the club.”

Sommer was able to visit Croatia and Belize and counts them among his most memorable trips. 

“I learned so much from the Singles on Sailboat skippers, including charting an itinerary, navigation skills and mooring techniques,” Sommer says. “In addition to fantastic sailing conditions, there was daily snorkeling off the barrier reef along the Belize southern cays that was incredible. I am sure the Bahamas —the Exumas—trip this year will soon be added to my best memories with SOS,” Sommers predicts.

Sommer came to the club with some sailing experience.

“I joined after my wife passed away,” Sommer says. “I was looking for a way to meet new friends and to sail on the Bay. I had previously sailed and prior to my wife’s passing we had moved to Annapolis from Silver Spring to further enjoy our love of kayaking and sailing.”

Previous sailing experience is not a requirement, the club is happy to provide it.

“I’ve already been paired with a mentor and this weekend I will attend two short seminars to learn about sailing preparation and knot tying skills,” says new member Melinda Whitfield.

Whitfield attended her first Singles on Sailboats event just last month. A fan of—a service used to organize groups that host in-person events for people with similar interests—Whitfield spotted the January Happy Hour gathering for Singles that Sail.

“I’ve always enjoyed being around water,” Whitfield says. “I’ve sailed a few times and I took a beginner class, but my work schedule and life tempo made it difficult to continue. Now that I have recently retired, I’m able to pick up where I left off.”

More than 20 current and potential members met at the Greene Turtle in Annapolis to talk sailing and socialize over food and drink.

“Many of the members took time to talk with me about the club and their sailing and social events and to offer tips and advice,” Whitfield says of her first club event. “I was happy to find that my lack of sailing experience would not be an issue. I felt so comfortable with the group that I became a member the very next day.” 

Once you’ve officially joined, the club wastes no time getting you out on the water. New members are required to take an orientation and a basic skills program is available.

It’s the club rule that members must be single at the time of joining. But you can pair up once you’re officially a member. And rumor has it that many a happy couple have met in the club and sailed off into the sunset together…