The boat in Wedding Crashers.
Correct! I'll post an update shortly
Wow! A wild guess based on one google search and a resemblance between the fitting at the boat end of the bowsprit in your photo and another photo I found. (Plus, I suppose, that your photos of the sails were vaguely consistent with the photos my search turned up.)
It was a googling skill test, which you clearly passed with flying colours. One clue was the number of masts leading to the phrase "schooner". If you search for "schooner" and "annapolis" then I think the woodwind should be the first item on the list returned. Plus actually I think I posted about it a few years ago.
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