Given my knowledge base. Aircraft/avionics tech of about 20 yrs exp, flight simmer, and 4 years of flight deck observer experience. I would be completely lost on a sailboat, especially anything of any significant size. I did have some childhood lessons in about a 12 footer. The terminology, the anticipation of actions needed for safe operation would probably be my largest fear/failure.
A large jet aircraft has all the same systems, flight control's etc. They react differently to an extent but automation levels the playing Field. Understanding the theory of how the cockpit is set up by the MFGR of the aircraft you are flying helps (show me the button to push to achieve the result I want). There are several cockpits I could make my way around blindfolded. My company just about expects it of us during annual recurrent testing. My answer is no, the average flight simmer would not have much of a chance, at all.