For what it's worth I have sailed and or motored through Plum Gut perhaps 150 times or more in every condition imaginable.
Unless it is slack or a fair tide I will have the motor on. I have tried to sail my 36' sloop in perfect wind conditions against the full tide and I can make a knot or two, but you can get set down on to Plum Island on the ebb. The current runs SE - NW or the reverse so consider the set. You can see some very confused roiling water in there and get slapped around by waves... but your boat can make it though no problem.
The passage can be a bit hairy because the fisherman bob around in there.. not anchored and are darting around. They will almost always get out of the way of a vessel passing through.
Plum Gut is plenty wide and deep. I have even seen a sailboat pass on the west side of the lighthouse! But only one.
I would set a course as close (200' perhaps to the light house as you feel comfortable and keep it abeam as you enter Gardiner's Bay and head toward Shelter Island.
If you are going to Dering Harbor you can sail close to the shore along Orient and easily pass half way between the R2 and Bug light.. there is plenty of water there. I suppose they set the R2 so far south because you can more easily fetch it from the gut. 99% of the vessels honor the R2 rrr.. I don't.
It is not as scary as some make it seems, but a decent motor is good to have and you might still consider using it while sailing in moderate conditions to have more control because of other traffic. You will have to deal with the ferry or even two. They run through there every hour, but again there is plenty of room.
Last edited by SanderO; 07-30-2007 at 01:06 PM.