Welcome!

SOS members have been enjoying a spectacular July! We welcomed the Tall Ships and celebrated SAIL250MD in Baltimore, spent Independence Day in St. Michael's, and recently gathered for our 48th Anniversary Cruise and Party at Maryland Yacht Club. With many more exciting cruises, day sails, and social events still to come, there's something for everyone—take a look at our Event Calendar!

Join the Singles on Sailboats community with a membership that offers a variety of sailing events, gatherings, and educational experiences. Whether you're a seasoned sailor or have never set foot on a boat, you're welcome here.

Our relaxed, friendly atmosphere means there's no pressure to attend every event or have any prior sailing experience. Come aboard and discover the joy of sailing at your own pace. 

New Member Application

 

Membership Benefits

  • Meet like-minded friends in our active social sailing community
  • Sail the Chesapeake Bay and/or Abroad
  • Robust sailing schedule April through October
  • Sailing opportunities are affordable and inclusive for all levels
  • Extensive educational and learning opportunities
  • Enjoy monthly brunches, fireside chats, and seminars in the winter
  • Mingle at regional Happy Hours
  • And more!