Winterizing the boat. Just the thought can send shivers down the spines of boat owners. For one, the timing generally means the end of a fun boating season. Plus, winterizing ranks low on the priority list of “fun” fall chores like raking leaves and cleaning gutters.Before blowing them all off, remember, those chores have a purpose. For boaters, winterizing keeps money in the fun budget, instead of being wasted on costly repairs.