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We've gone through quite the gambit of coolers on this boat.  Generally the idea is to bungee it to the transom underneath the tiller, since there's so much real estate back there.  Of course the trouble is that the height is quite restricted.

  1. The hard igloo
    1. Doesn't fit under the tiller
    2. Flies off the transom during evasive maneuvering forcing an impromptu race restart
  2. The collapsible bucket
    1. holds a buncha stuff
    2. gets smaller as the stuff gets drunk
    3. doesn't really insulate for long durations
    4. does not retain contents in event to capsize
  3. The soft cooler
    1. space is restricted
    2. flexible construction means it probably won't last through the season.
  4. The frozen gatorades in the Chute bag
    1. things go flying when it gets wet and wild on hoists.