Nick
I don't know how tight things are at Brewers but have you seen/tried Mitchell Park Marina in
Greenport?
It's really nice, no wave action, new docks, concerts in the park etc, etc. We've stayed there several times & highly suggest it!
As far as NYC, Coffee colored water, pilings floating by at 5kts, Hudson River white fish. yuck! It's only a 40 run for us but with the ice ripping apart marinas, pulling pilings out & ripping lose anything that hasn't moved in 40 years, I'm not headed in that direction for a while. Kidding aside (yuck), everyone should be really careful this spring, summer. There is going to be lots of stuff floating out there. I know at my winter marina, they literally lost (as in gone) lots of pilings due to the ice pulling them out.
As far as another destination for another rendezvous, what about Essex Is. Marina? It's a little closer or better yet, Northport is a favorite for us, only a 40 min run, nice Town.