As the Ten Most Superlative Days of Summer draw to a close, let us examine the history of the Skipper Pin. I've been meaning to do this for years, but always forget. It's a rare day you get up and say "hey, I should scan those Aquatennial pins." But I finally did. Here's the classic design:

That's as basic as it gets, and it works well. The font is a little spiky, but that would be solved the next year:

In case you're wondering if such a simple design could ever be bad: why, yes.

This is from an auction sale - you can buy it for $9.50. The UP stands for Unity Pride, just to complete the hippy-dippy 1969 feel. Nothing was ever as Square as government organizations trying to be Relevant, and Rap with the people in a Meaningful way.
The Milk Carton races are given their due on the 2000 pin:

Things are starting to go off the rails the next year - the "Skipper" font is just wacky! and the combination ship-wheel and anchor look like botched vivisection.

Oh heavens no:
Because the thing most people associate with a water-based community event is a brass band.