Made the trip a few times. Assume you have looked at the charts
Many of the decisions on when and what route
will be weather
From CT down LI Sound you will transit the East River and Hell Gate. Check current
before you go. LI Sound fills and empties through the East River and the Race
on the other side and current
can top 5 kts at times. Also the East River west of Roosevelt Island closes occasionally when a big wig visits the UN but I think the east passage
is open BUT there's a 40' draw bridge on that side.
From NY you're outside on the Jersey Shore until you reach DE Bay. You can go all the way up DE Bay to the C&D Canal
, all the way back down the Chesapeake. Do it for the scenery if you like but it's shorter and faster outside again to Norfolk.
Norfolk south you have the ICW
so you can travel the inside if it's blowing. But unless you're brave (or foolish) and experienced you will not want to run ICW
at night so longer transit. My luck I always hit bad weather
at Hatteras so go inside from Norfolk to Moorehead City then go outside again.
From Charleston south to FL line all the harbors and inlets are very long channels from the ocean to inside, like 15-20 miles so you waste a lot of time trying to harbor hop that stretch. I usually jump straight from Charleston to Jax or Brunswick.
From there south you can go inside or outside but from Palm Beach south you run the gauntlet of bridge after bridge.