Join Date: Feb 2002
Location: VIrginia Beach
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Like CS I used to single hand my 26 Islander all the time. For the first 3 years I had to go to the mast to raise and lower the main. I have also changed out the hanked on head sail many times due to weather changes. The key is to pay attention and make changes and reef in advance to changing conditions.
My tiller tender was three bungee cords which allowed a little play in the tiller but kept the boat pointed into the wind. I also would center the main which would help keep the boat pointed into the wind.
After the 3rd year I decided to run the halyards aft to the cockpit along with the reefing lines. Still found myself on occasion having to go to the mast or for peak to take a sail down or untangle something.
I guess to answer your question it's fairly common to single hand without having all lines running aft. I am assuming you have the jib sheets running to the cockpit.
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