I haven't seen anyone do this without somewhat securing the blanket or towel to a rack on the back of the car, and it is advisable to do so anyway because otherwise the boat can move them around as you slide it up.
I have never had wind blow up something like the fleece blanket that I use on the ground. If it is so windy that it could blow that off the ground, I am not sure that paddling is a great idea.
The Kayak Wing
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