Our smaller ship, the Owl, is often charted for multiple days. When we have a multiple day trip, we sail people to an Inn, on one of the various islands in Penobscot bay. Then the following day, we pick them up and sail home or take them to another island the next day.
I don't know about nights. We went out for a couple of hours to have our wedding ceremony on the Owl. We weren't expected to do anything in particular, but I suspect you could if you wanted. The Owl is the smaller one.
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