I enjoyed reading your wind stories, NWG. High wind is definitely not funny. We've kayaked in some pretty windy conditions, not dangerous, but just bad enough that it could take 4x as long to return to your starting point as when heading out. I remember some very sore shoulders after that! We quickly learned to head into the wind first if at all possible.
We also owned a sailboat (Catalina 30) for three years. I much preferred sailing in lighter winds even if it meant a "boring" sail, as when the wind started freshening, at some point it could become scary, sometimes rather quickly. There are obviously things to do to deal with it (reefing sails, and so forth), but I always tended to get in a bit of a panic. Wind also caused choppy waves where we sailed (Neuse River area of NC), and just like your canoe story, we would have to aim the boat into the waves so as not to be hit broadside. Not comfortable sailing at all, nor any fun. We also spent one very looooong night in the boat in our marina slip during a Cat. 1 hurricane, and got blown all night after the power went out. It was super uncomfortable and scary. We had done our prep and all was well, but the boat was banging into the pilings (with fenders in between) all night long. Not many winks of sleep that night! I loved being in the boat and on the water when conditions were mild, but I had no interest in heavy-weather sailing, which is one reason we eventually sold her.
Looks like we're in for another breezy ride today but not quite as windy as Tuesday, at least per the forecast (10-20 mph SSE).
Emily
2011 Jamis Dakar XC "Toto" - Selle Italia Ldy Gel Flow
2007 Trek Pilot 5.0 WSD "Gloria" - Selle Italia Diva Gel Flow
2004 Bike Friday Petite Pocket Crusoe - Selle Italia Diva Gel Flow