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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

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.

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Come sail with us - attend our Meetups, learn about the club, join us sailing on the Bay

  • 5 days ago · 5:00 PM

    Join our party at the DNR on Wye Island

    11 Sailors

    SOS club members are sailing to this destination, looking forward to our traditional first onshore weekend party. The theme is 'love in the 60's. Come in your tie died... Learn more
  • May 18 · 6:00 PM


    1 Member

    700 members - singles who sail the Chesapeake,Over 70 boats and 30% women skippers.  Come join us ! enjoy drinks and good company, we raft on many weekends April through... Learn more
  • May 18 · 5:00 PM

    SOS Bethesda Happy Hour

    2 Sailors

    Location has changed - see above. Meet our members, talk some sailing, learn about the club and it's activities.
  • May 17 · 5:30 PM

    SOS Wilmington Happy Hour

    5 Sailors

    Meet our members, talk shop, learn about our club and the opportunities it offers to participate in the sport.
  • May 11 · 5:30 PM

    SOS Happy Hour - Baltimore County

    5 Sailors

    Meet members of the SOS club, learn about our activities, consider joining if you're not already a member.
  • More Meetups

What's new

  • Alex Doyle founded Singles on Sailboats

    on August 3

Founded Aug 3, 2010

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