I wouldn't waste my time or his asking him how they did it without GPS - it's of little value to me or him. But the OP's is a nice question.
If I wanted to show off technology I guess I'd show him Google Earth.
If I wanted to show off boat equipment I think I'd show him the auto-pilot.
If I wanted to show him sailing technique I'd take the boat to weather and beat at 8 knots.
I wouldn't waste time with Pussers (other than maybe sharing some) because nothing has really changed there.
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"Two possibilities exist: Either we are alone in the Universe or we are not. Both are equally terrifying."
Arthur C. Clarke