Fleet 5 is an energetic group of Cruisers. Each member of our fleet thrives on the camaraderie of the sailing and cruising lifestyle. We are dedicated sailors, cruisers and occasional racers. Members of Fleet 5 are ready to lend advice on any boat topic. We share the knowledge of our cruising destinations, the fascinating harbors we have explored, and the great restaurants we have enjoyed. We have a passion for this lifestyle, take great joy in the journey of our trips and take the time to ensure our travels are safety minded and well prepared. Of course there is always time to chat about the improvements we have made to our vessels and at times our unfortunate repairs.

Recent News

New Membership Program

New Membership Program is in place. First year members can sign up for only $10. Joining our club will quickly expand your circle of nautical friendships. Just go to the member section of this website and join.


  • Fish Tail Cruise

    Meet in Greenport, Long Island and spend the next seven days relaxing in and around Shelter Island. Two-day stops at Sag Harbor, Coecles Harbor and Montauk Point. See More Details

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