Autumn is def the best time of year for the kind of sailing I enjoy most, in good winds pushing the boat to its limits.
You can see Manhattan under the low side starting at about 2:00
However this is also a season for added precaution.
My father was on LI sound Saturday about 5 miles east of Port Jefferson towards the end of the day, cruising back from Block Island on his c&c 32, when the coast guard came on Channel 16 and advised all small craft to find shelter because "40 knot winds and 10' seas" were a-coming. Well the front swept in shortly after, and fortunately he already had sail down and was under motor making way to shelter. Once it hit he was only able make about 2 knots at full power into the wind and waves and it took him hours to make it into the harbor. He heard on the radio that one boater was not so lucky, and had called for rescue just outside of Port Jefferson harbor. Throughout the night he says his boat was shaking in the wind, and he was pretty happy about having just bought an oversized plow type anchor for the trip.
Last weekend, during a distance phrf race, we saw a front moving in but stayed powered up anyway, full main and 155 genny. It was 3-4 miles away, so we figured we had some time before it hit. Wrong. Thirty seconds later we got a massive wind shift, autotacked and then just as we lost nearly all speed a tremendous gust caught us. It started blowing at least 22-25 knots and the boat got knocked down severely. It was spreaders in the water, with the guys on the low side literally
swimming/floating above the lifelines as the boat was pinned at over 90 degrees for probably 10 seconds. Finally the cockpit crew was able to get the sheet released (funny how difficult it becomes to do this at 90 degrees) and we wound up taking the main down until we got control of the boat. Racers are great at going fast, but not at tying in reefs
(they have no practice I guess haha) so my cruising experience for the first time became an asset to the overall effort and we finally got a reef in and were able to power into the 4-5 foot waves that had suddenly come up as the wind was just beginning to subside. About 40 minutes later the front had passed and there was little more than a whisper on the water and a huge rainbow behind us:
Autumn makes for great sailing I must say