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Default Long Island Sound -- Planning Possible Spring/Summer Cruise

In the process of planning a possible spring and/or summer cruise in
Long Island Sound and nearby, after shipping "Gambier," a Eastbay 43,
drawing four feet, by truck from Ft. Lauderdale to probably northern NJ
for offloading and pick-up, I am asking for suggestions and comments
about:

How early ought one to begin a cruise on the Sound?
Crowdedness in general on the Sound?
Crowdedness in ??? ports, marinas, anchorages?
Better and best anchorages and marinas?
Better and best villages, towns and cities to visit, and why?
Best fuel (deisel) sources?
Your best comments and advise re cruising Long Island Sound?
Thanks much.

Ed Wagner
m/v Gambier