Welcome!

Join our 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, everyone is welcome here.

Enjoy a casual atmosphere with no pressure to attend or have any prior experience of sailing. Come aboard and explore the joys of sailing at your own pace. 

Take advantage of our New Member Special! Join now and receive the rest of 2025 and all of 2026 for the same price!

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!

Read our Newsletter!
October Whisker Pole