No Way
I have 2 friends with 2 houses at watch hill and always tried to get me to keep my boat there,no water for any kind of good sailing before you will be bored and yes pretty good wind but no real water.
When I sailed my Hobie Cat yes great fun and plenty of wind and great place to sail all over with a smaller boat like sunfish or Hobie cat,bayshore area I new people with sailboats but they were not always very happy and had to be very careful of all the shallow water,just look at all the power boats running up on sand bars and sucking up sand into the engine.
I stayed in the peconic and than moved my boat to Greenport.
LI is a great place with so many great places for boating and do miss it some times.
Nick