Just go the whole way around, none of the inlets along the south shore of Long Island
are advisable, the currents rip, the sand bars shift constantly, and if you do get in without running aground the water is pretty skinny everywhere, all sand so soft landings if you bump bottom but not really someplace I'd want to be in anything with a good bit of draft and no local knowledge, even in broad daylight. The north shore through the sound has far more options for overnight stays, the easiest from that area would be Port Jefferson, you would likely be there before dark and it's a nice secure anchorage to spend a night.
If you do the outside you can head
in between the forks and anchor
up in Lake Montauk or head
a little further west and you have Cocles Harbor in Shelter Island or 3 mile harbor on the south fork or you can go a little further north and anchor
up in Orient Harbor just south of Bug Light, there is good holding in there and it is usually pretty calm, just watch out for the fish
weir toward the western tip of Long Beach, it is on the chart but not always easy to see but this one would be the easiest at night as the other options all have tricky inlets to navigate if you are not familiar with them.
Originally Posted by wizoc
Coming down the sound ebb at Hellís Gate is 10:18. Considering options.
Just continue non-stop to Montauk
Stop East Rockaway or Jones Beach
Some other stop.
It will be 2 people in a Catalina
425 with a 5ft. draft.