[Minnewaska]

......this jump off point extends my range by 48 hours of actual sailing miles.

If this is your motivation, I would go up the CT shoreline to the Mystic area. I dare say, you could drive to southern RI in the same time it will take to transit Long Island, then you would really have your cruising options open.

 

[Minnewaska]

The train is a great idea. For giggles, I just checked Amtrak from Penn Station to Mystic. A 3hr train ride is no doubt faster than driving to Greenport.

I'm only hung up on Mystic, as I think it's roughly equidistant and, IMO, offers better cruising options. To get out of Greenport, you essentially need to deal with the Race or at least be exposed to ocean conditions. Mystic is protected by Fisher's Island Sound and is closer to popular New England destinations.

 

[Minnewaska]

....Ever get on I-95 East on a Friday in the summer?.....

Sure have. I think I get frequent rider miles. Helpful to get a jump on it or leave late.

No doubt, there are choke points on I-95. However, there is nothing on this planet as tough as the Long Island Expressway. I will take the CT route over Long Island.