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.
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 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 pained $27,000 one of those items.
Fearing that his shot-ski game might be getting stale, Miles took a few years off making them for the Key West event, which benefits Samuel’s House and AHEC Health Center this year. But now he’s coming back with one for the 2025 affair set for Thursday evening, November 6, and the Pickle’s Pub Sandbar on Greene Street.
Our goal for the item simple: We want it to bring in a lot of money—maybe even break the existing $27,000 record for the item—for the charities, both of which have 501(c)(3) nonprofit status. Winning bidders will be required to pay immediately after the bidding on each auction item closes. No exceptions will be made.
One more rule? The winner bidder and his or her friends will have to take a shot before the crowd.