Paddling big lakes with big tailwinds is a skill that I haven’t seen discussed in the books, but it takes a certain knack to not get spun by the waves. Once you get spun, it’s easy for the waves to come over the gunwhales and fill your boat with water. In most cases it’s really fun being pushed along by the wind. But it can also be challenging and nerve-wracking. And the waves never look as big from shore as they do from the boat.
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I’ll take a tail wind over a head wind (or even a quartering wind) anytime! Paddling solo I always feel like a shuttlecock when going a direction other than with the wind.