And because the apparent wind was about 15-degrees Port at 30-35 knots. We needed to point higher than we could sail to make the passage between Gardiners Island and Plum/Orient Point without tacking. We could have bore off about another 15-degrees to port and sailed without engine assistance but that would have run us into Plum Island or Orient Point in no time, so we slogged into the wind and heavy waves keeping down to about 4-5 knots boat speed just to go easy on the boat and ourselves. I also though these conditions would abate as we got closer to the lee of Gardiners Island and then into Gardiners Bay (they didn't abate until we got close to Shelter Island).
We had decided it would be nice to go into the Gardiners Bay area, as we hadn't been there in a few years. We should have just bore off to the north and sailed to Connecticut on a deep reach, but the forecast for the following day was for SW winds and we were working our way back to eventually western LIS. So I wanted better sailing the following day, and starting out from LI would be a better sail than from anywhere on the CT side.
In hindsight it was just a bad decision to bash today in hopes of better sailing tomorrow. We could have bore off to the north and had a great sail, fast.... deep reaching without discomfort. The wide-angle of the point-and-shoot lens doesn't really show it, but we were up and down 4-6 feet with every wave. Even more at the port and center bows. You can get a sense for how high our up and down motion is if you look between 0:40 and 0:50 in the video.