Note the size of the visitors on this...ahem...tall ship.
I would see the nose of the train first—coming or going.
I used “generational” to infer the eventual advent of square-riggers that would carry topgallant, royal- and sky-sails.
Columbus probably already knew of the earth’s roundness from personal experience at the masthead. He and his crew would see an approaching ship’s masthead before seeing the deck, as stated previously.