Join Date: Jun 2012
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Re: Has anybody towed kayaks behind....
Borrowing from my river paddling experience....
Canoe trippers sometimes walk their boats upstream with a practice called "lining". One or two people walk along the river bank and guide the boat upstream against some pretty stiff current and even big rapids. If you simply attach a long painter to the stem of the canoe, it will eventually dig in and flip - but savvy canoeists will rig a bridle that goes under the boat aft of the bow with a center attachment point for the line. This causes the boat to run bow-loose and ride up over the current and waves without digging in. It pulls easier and it's much easier to control the bow - eliminating the danger of rolling the boat.
Kayaks aren't designed in a way that allows easy rigging of such a bridle, but with proper motivation, I bet it wouldn't be hard to come up with a way to do something similar. I believe it's a given that it will slow your sailboat some, but I'd be surprised if the kayak with a proper tow bridle didn't follow nicely (in good weather). No, I haven't tried it....yet.