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my2fish
I was sailing earlier this year and a gentleman brought down a kayak with side outriggers and a mast with a square-rigged sail. His sail was the pirate "Jolly Roger", and he was dressed in full pirate ensemble, with a hat and everything. The icing on the cake - a stuffed parrot mounted to the top of the upper sail boom.

A live chihuahua is better than a stuffed parrot any day, so I'd say go for it!
 
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