Join Date: Jul 2008
Location: Jacksonville, Fl
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Having done a lot of single handing, my personal recommendation is to bring everything you can into the cockpit. Going out on the deck when you're out there alone is not something you want to do unless you don't have a choice.
Even now, when I'm alone on Island Breeze, which is 56' long, I try to stay in the cockpit once I'm out of the Marina and have the fenders, dock lines, etc., stowed. Even then, when I'm alone, in flat calm, motoring with the autopilot driving, if I leave the cockpit, I have my SOSpenders on and the tether attached to the boat someplace, usually the jackline, but not always.
When the wind gets above 15 knots, I'm attached to the boat. An hour before sunset, even in flat calm and in the cockpit, I'm attached to the boat, and after dark, there has to be a life or death reason for me to leave the cockpit. Raising or lowering sails should be as safe as you can make it, and going to the mast, at night, in a squall, is not something you want to do.
As for your choice in sizes, go for it. I single-handed a 29 footer LA to Hawaii. Just make sure the boat is built to take it, and is equipped properly. Last time: Stay In The Cockpit. Going for a swim in the middle of the Pacific (or Carribean or the Bank) and watching your boat sail off means you are having a very bad day, indeed. Hook yourself to the boat. Period.
That, btw, is experience. I was motoring out of Long Beach alone one day, autopilot on, not much wind, small seas, and went to hank on the jib. To make a long story short, I was very glad I'd put nylon lifeline nets on the boat, or I would have been swimming without a life jacket and my boat and dogs would have gone to Two Harbors without me.
Since that day, I have always worn a harness when I'm out alone, or even if I'm standing a midnight watch alone on a fully-crewed boat.