Join Date: Oct 2009
Location: Gloucester, MA
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That is quite a video. I wouldn't want to be the one responsible for doing it.
What about looking at a boat that has a short enough mast to clear the bridge so that you don't need to drop it. This generally means that you need a way to get the same sail area with a shorter mast. This can be accomplished with lug rigged, sprit rigged and gaff rigged vessels. If you are looking for something large enough for the family, a ketch would probably be necessary.
Unfortunately, you are not likely to find any production boats rigged like this but there are lots of old pulling boats, whaleboats, etc that are rigged this way. They certainly are not sporty but they might have a higher enjoyment factor if you don't mess around with dropping the mast all the time.