Tojaso...welcome to the light. I voted no given the extreme cold, snow and ice at that time of year plus the issues of breakdowns on a new to you boat that you will face in a 1500 mile+ journey.
There have been FOUR sailboats rescued off the coast in the last 10 days and the weather is WAY better now than it will be when you plan to go.
If you DO decide to go for it anyway...I suggest you stay in the ICW all the way to mitigate the weather and give yourself someplace to duck in each nite. You will HAVE to go offshore along the Jersey Coast...but there are 3 usable inlets there before you get to NYC.
I would estimate 45 days for the trip at that time of year.
Good luck in any case and your service is most appreciated.
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