I have done this route
as well as the LI Sound route several times in my 30' O'day. Here are some items to be aware of on your trip:
*Weather - The southern side of Long Island
has relatively few harbors suitable for sailboats. Try for a good window.
*Fatigue - It's a long trip to singlehand, since you are close to shore and will encounter heavy traffic. Me and my wife together even were up against some fatigue doing this trip in a shot without stopping. Hopefully, you have some crew to make it less tiring.
*Traffic - The commercial
vessels going into NY Harbor and Buzzards Bay / Long Island Sound
are numerous. Frequenly, you will find tugs pulling barges with extremely long steel cables
between the two. Be very aware of this setup at night and in when visibility is reduced. A fair number of boats (both private and commercial) have fallen victim to this tug/barge setup.
When do you leave? Soon? It will be a chilly one this time of year!