What we're about

The Chesapeake Sailing Association was founded as a singles sailing club more than 30 years ago to bring skippers and crew together to enjoy the beauty of the Chesapeake Bay.

Over the years, we have evolved into a group of those who enjoy getting together for all kinds of events, both nautical and social, mostly around the Chesapeake Bay but sometimes beyond!

We have sailing and power-boat events hosted by boat-owning members and also now include a variety of other events such as occasional day trips on commercial cruise boats on the Chesapeake, as well as Happy Hours/Dinners at waterfront restaurants.

We encourage all members to host events that may be of interest to others who like being on or by the water!

Please see the "Pages" menu item for FAQs about the Group at the following link:


Upcoming events (3)

BCSC Memorial Day weekend May 24 thru 27

2200 Rocky Point Rd

Baltimore County Sailing Center is starting the summer season with a bang! You can rent kayaks, sailboats and paddleboards all weekend long. There will be live music Friday evening, and most of the day Sat, Sun and Monday. Come on down and enjoy some fun and friendship by the water, since the weather will be great.

Memorial Day Weekend Visit Sail

Tucker Street, West Annapolis

If you'll be in the area, or just want to visit my boat call in advance for a tour and sailboat outing. I'm anchored in the Weems Creek at the end of Tucker Street.

Sail to Newport, Rhode island

Needs a location

TBD IN Mid June Contact me on[masked] if interested

Past events (674)

Photos (2,720)