Miles Creating The Mother Of All Shot Skis For SOTW Key West Bash Auction

Of all the items you’ll see up for a bid during a high-performance powerboating-event charity auction, the most useless but often coveted is the venerable shot-ski. For the uninitiated, a shot-ski is an old water-ski with the bindings removed and several shot glasses mounted in their place. The setup enables three or more people to simultaneously and carefully—key word—take a shot of whatever spirit they choose.

Performance-boating events have raised the lowly shot-ski to a big-buck-bid artform.

Of course, given the raw materials, a bit of desire and too much time on your hands you can make your own shot-ski. But what you can’t do—unless you happen to be a generous Southern gentlemen named Stephen Miles—is dress it in a Stephen Miles Design paintjob. And that makes them valuable, at least as auction items. Shot-skis painted by Miles have fetched an average of $10,000 at Speed On The Water Key West Bash charity auctions during the years.

If that sounds like a lot of money for a slab of painted wood with three 50-cent shot glasses glued to its surface, it is. But during the 2022 Kuttawa Cannonball Run charity auction in Kentucky, the winning bidder paid $31,000 for one of those items.

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