Boat: CS36Merlin, "La Belle Aurore" Ben393 "Breathless"
Re: Air draft 65 ft in ICW (VA and NC)
The hardest part will be the bridge in the Alligator/Pungo canal. Many times it is less than 65'. The waterdepth depends on the wind here, not tides so you can't even wait for low water. You can avoid this by going out Albemarle Sound and then inside the barrier islands. I have not done this and am unfamiliar with water depths there. Myself, I would not attempt the ICW with 65'.
Take two sailbags in good condition and if you have any doubts about your height attach the sailbags to the main halyard and a keeper, fill them with water and leave them hanging over the side, this will tilt your boat about 8 to 10 degrees and line up your top of mast with the red and slowly maneuver your way under the bridge,