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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.
 
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