Serene destinations near NYC

[Yudhishthira]

First off, I love this Forum. I have been reading obsessivly, and now its time to start posting.

So...I need a little bit of help coming up with a nearby weekend destination. I am fairly new to sailing, and I have a new to me 27' Hunter moored in NYC (79th st.). For my birthday I would like to grab a few friends and head out for a weekend trip. It's taking the place of my summer camping trip, so hopefully something serene and private. Maybe with some nice swimming and hiking nearby? It will be my first overnight- so I am hoping to find something challenging but not TOOO terrifying. I would like to anchor (to save money) which is something I have never done- so a nice easy anchorage would be great. I was thinking south shore of long island, or Sandy Point, or maybe even further up the Hudson

Anyone have any ideas? Something that meets at least some of these criteria: Only a days sail away from Manhattan, Clean water to swim in, Easy anchoring, and Good sailing in the area. I need a break from sailing New York Harbor!

I'll take as many ideas as I can get...perhaps I can make a couple trips this summer. Thanks!!

[CalebD]

I would get tired of just sailing in NY Harbor too.
My boat is up the Hudson just above the Tappan Zee Bridge at Nyack and it is pretty and fairly quiet up there. People anchor overnight off Croton Point or across the river at Bowline Point. This area is a good 7 hours travel by boat from 79th st. The water is brackish and for swimming I prefer the salty waters of the LI Sound.
You should be able to go around Manhattan and up the East River but you will need to check the tides and currents in something like the Eldridge Tide & Pilot manual so you don't battle an opposing current. It is actually a fun trip and a little bit challenging but you should be able to reach the City Island/Manhasset Bay area in around 4 hours. About 2 hours farther is Hempstead Harbor which has places to anchor or pick up a transient mooring for around $40/night.
Then there is Raritan Bay to the south. RYC probably has transient moorings as well. Maybe not so bucolic but not so far either.
Transient moorings at Nyack Boat Club are still $25/night and it is a pretty river town.
Good luck and have fun.

[Tempest]

A couple of more options might be:

Atlantic Higlands you can anchor or grab a town mooring.

Great Kills on staten island

Horseshoe Cove, behind Sandy Hook..

[helenwiley]

Has anyone taken the outside of Long Island instead of going the East River? We are going to our mooring in Winthrop, MA, the end of May and would like an alternate route instead of going long Island Sound. I have done some reading, and it sounds doable for a 4.5" draft boat with the mast down.