We've done it multiple times (not at night). There are multiple factors involved:
--Wind/wave/ how many people in the dinghy (try to sit behind a big, fat person).
--If you only have 2 or 3 riders and can get the dinghy up on plane > yippee.
-- If its very windy, head over towards prickly pear island and then navigate its leeward side. If you get there and a divorce is now pending, let the fun-police ride back over on the Saba rock ferry.
-- Remember, when you get about half way across the sound, start throttling up and down and claim you think its outta gas.