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

  • Sail the Cheseapeake Bay and/or Abroad
  • Lunch and Learn at our winter brunches
  • Learn some sailing basics at Dockside Training
  • Enjoy meeting members in their homes at Fireside Chats
  • Join fellow members for Thanksgiving and Christmas Dinners
  • Cheer us on at the annual Eastport Yacht Club Lights Parade
  • And more!

Read our Newsletter!
October Whisker Pole