[CalebD]

I know it is not near City Island but there are 16 recently installed moorings just south of Pier 40 (Houston St.) that are also operated by NYC Parks Dept. The moorings are attached to 8' x 8' x 1' cement slabs and their buoys have been attached all winter. Presumably they don't officially 'open' until May 1st as well but the moorings are there. You need a dink to get to shore if you stay here. The website lists a $40/night transient charge though you may have a hard time finding someone to take your money.
Also in this area Liberty Landing rents their transient slips for $2.50/ft/night until May 15th when the price jumps up to $4/ft/night.
There is a little better sailing up by City Island though, IMHO.

 

[CalebD]

I was trying not to come right out and say this but the folks that run pier 40 are city employees and, as such, may not be so diligent about their duties. I have referred other boaters to this mooring field this past fall and at least one boat was able to spend the night for free. The 79th st. facility on the other hand is a real marina with a 24/7 harbor master - in season.
The deal BarryL linked to in Manhassett Harbor may be the best deal that close to NYC on the Sound.
If you were willing to keep on going up the Hudson I'm pretty sure that Nyack Boat Club has transient moorings that are $25/night as well. It is pretty up there and is where my Tartan 27' will be moored starting April 10th. It is about 25 nm. up river from pier 40 though and an hour or less drive from Tribeca on a good day.

thanks... yes, was a bit disappointed with pier 40; tried called so many times this past month to try to get a mooring for the season or a couple of months but could never get through. once i did informed me no availability (probably why they weren't taking calls). and yes confirmed the others.

did find minneford marina in city island that can do $1.50/ft/nt which is probably best i'm going to find. just disturbing that for 2 weeks going to have to spend almost half of what i'm paying for the entire season for the 79th st mooring......

 

[CalebD]

Pier 40 is a 10 minute walk from where I am. I have not stayed there yet but would like to at some point even if it is in stealth mooring mode.
One of the few decent anchorages in the lower Hudson is behind a place called Bowline Point near Haverstraw - google it for future reference.
The trip up to Cold Spring is gor-diddley-orgeous!
Since you have some options, why not save the trip to Shelter Island for warmer weather? I'll bet you would be tempted to go this weekend though.