About us
The Meetup Singles on Sailboats Group is a vehicle to introduce prospective members to our club.
The club is an organization of singles in the Chesapeake Bay area (over 700 members) who enjoy sailing, or want to get involved in the sport. Members include skippers (boat owners - about 125) and crew looking for OPB's (other peoples boats) to sail on.
Experienced and novice sailors are welcome, and the club offers extensive learning experiences. Activities include a busy schedule of day sails, weekend cruises, and extended 10-day cruises during the sailing season (April thru November), and many social get-togethers during the off-season.
We also organize one or two bareboat charter events every year, to destinations literally around the world. Recent destinations have included several to the Carribbean, Australia, Lake Huron, Croatia For more info, visit our website at www.SinglesonSailboats.org.
Through the Meetup website we offer year-round monthly happy hours throughout the northern Chesapeake Bay area. These are located from southeastern Pa to northern VA, and numerous points in between. They are attended by both Meetup participants and active club members. Active members do not RSVP through Meetup, so you will find many more attendees at these events than this site might indicate.
During the off-season (November through March) we also offer monthly Sunday Brunches in Annapolis. These typically attract over 100 attendees, and always include a speaker on a subject of interest. Speakers have included noted authors, Bay Pilots, outdoors & nature photographers, celebrated sailors, among others.
Members and non-members are welcome at the happy hours and brunches, all posted on this site. We invite you to participate in our Meetups, meet club members, talk sailing, and consider joing the club.
Upcoming events
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- $35.00
Welcome Aboard Dock to Deck a day of sailing education
Castle Harbor Marina, 301 Tackle Circle, Chester, MD, USHave you ever wondered about Singles on Sailboats -- the actual club? I know you are on this Meet Up site, but did you see in our description that we are an active club? We are having a "Welcome Aboard, Dock to Deck" day on April 25, 2026. It is designed for newer club members, potential members, people who wonder about Singles on Sailboats and may want to learn more. There will be a morning session on Kent Island at Queens Landing Clubhouse with instructional sessions including Sailing Fundamentals session given by Kristen Berry (Gale Force Sailing) and after lunch participants will go to Castle Marina where several of our skippers will have their boats available to do dockside training on equipment, winches, radio, knots, etc. The day of education will end with a gathering and Happy Hour at a local watering hole. You can register at http://www.singlesonsailboats.org, look at the red button "Event Calendar" for April 25, and scroll down to register. You do NOT need to be a member of singles on sailboats to participate in this day. Hope to see you there.
5 attendees
Past events
1891
Group links
Organizers
Members
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