Daysailer Membership


A Daysailer Membership allows you to use the Ensigns and other daysailers as often as you want for a low yearly fee. You can take out the boat with whomever you want, as often as you want. It’s your boat. Members may only have one daysailer reservation outstanding at a time.

Five Day Membership (Monday thru Friday excluding Holidays)  Total Cost $1,913
Seven Day Membership  Total Cost  $3110  
Both memberships allow Unlimited Yearly Use.
7 Day Daysailer Memberships now included with all Yacht Memberships at no extra charge.

  • We offer a loyalty program for members with over 2 years of membership. Members with over 2 years of membership receive an extra 1% off renewal (6% total discount), over 4 years of membership an extra 2 % (7% total discount) and over 6 years an additional 3% off (8% total discount).                                                                                                                                                                                                                  

2020 Summer Schedule Time Slots

Morning 8:00 am – 1:00 pm
Afternoon  1:30 pm – 5:30 pm
Sunset Sail  5:45 pm – 8:45 (or dusk)

Please email sscsailing@gmail.com or call 203.838.1110 for more information about our membership program

Covid 19 Update –  Members have been out sailing the Ensigns more than ever, and many have mentioned how thankful they are to be able to get away, and that we never closed.  Of course, there are some restrictions on big boat use, and we are cleaning the boats between uses.  Please contact us for more information on what we are doing.

Our primary daysailers are Pearson Ensigns. They are a strong , unsinkable fiberglass boat that is still actively raced (and still being built). This is more than 30 years after her introduction. Ensigns are probably the most comfortable daysailer ever built. They have high backrests and a large, deep cockpit. The Ensigns are ideal for families or relaxing picnic cruises. Their cockpits are larger than even our J44. Just as important for us is that Ensigns, with our unique modifications, are the easiest daysailers to singlehand that we know of. We have many members in their 60s to 70s, men and women. They love being able to easily singlehand our boats.

Teak & Mahogany Comfort

The warm teak or varnished mahogany woodwork in the cockpit is a welcome change from the all-fiberglass construction of modern boats. The strong hull means you never have to worry about running aground or other minor mishaps.

We have a fleet of eight Ensigns. They use clean, quiet electric motors to get you off the dock and bring you back if the wind dies. All Ensigns have roller furling jibs and Dutchman self-flaking mains with low friction UHMW track systems. All lines are in easy reach of the skipper for easy singlehanding. Ensigns are sailed within two nautical miles of the Norwalk Islands. They are a six mile long chain of nine major islands, and many smaller ones. Our base is in the center of these islands. Most of the islands are nature preserves.

All Daysailers have VHF radios for calling in or for the latest marine weather reports, depth recorders, first aid kits, charts, and all the standard USCG safety equipment.