Join Date: May 2006
Location: Chesapeake Bay, MD
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I had tiller steering on my Dufour 27 that I sailed about 10 years ago. I used the bungy gadget that slides back and forth to hold the tiller in place while I set sails. An autopilot is very nice but not critical if you plan to single hand locally.
I also singlehanded my Hunter 37 Cherubini extensively. I think PB is right, hit the reefs early and plan for the unexpected. When it comes to docking, again, its not difficult. Just look for the wind direction and grab the rope that will hold you in the slip first. In other words, if the wind is on the nose, grab your bow lines. (Assuming your are back into the slip). Tie them off and then work on your stern lines.
In my opinion, singlehanding in terms of difficulty is overrated. Most people singlehand their boats most of the time and just do not realize it. For example, when you sail with you friends or even your spouse, you tend to do everything anyway.