Welcome!

Singles on Sailboats kicked off the Cruising season with a weekend at DNR Duck Lodge Granary Creek and the Wye River. Sixty-seven members of all experience levels participated. Visit our Event Calendar to discover upcoming activities that might interest you.

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 experience of sailing. Come aboard and discover the joys 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!