The only bit I would want to contribute is - as Skippy19 also mentioned - I think the single-handed sailor is Chichester himself and the song isn't so much that he was actually there at 2:00am (he could have been several times!), but more that if he were there this is just Mark's imagining what Chichester would have done/said. It's really a negative or forsaken attitude portrayed toward the sailboat (Gypsy Moth IV) which was factual - Chichester disliked it very much after the global journey and didn't hesitate to quickly detach from it for several reasons ("...sailing away in the dark"). Found this after reading up a bit on the topic.
Mother and baby are just referring to the Cutty Sark (mother, larger) and the Gypsy Moth IV (baby, being much smaller). They were next to each other at one point, perhaps they still are.
I love all the contributions, thanks folks.
The only bit I would want to contribute is - as Skippy19 also mentioned - I think the single-handed sailor is Chichester himself and the song isn't so much that he was actually there at 2:00am (he could have been several times!), but more that if he were there this is just Mark's imagining what Chichester would have done/said. It's really a negative or forsaken attitude portrayed toward the sailboat (Gypsy Moth IV) which was factual - Chichester disliked it very much after the global journey and didn't hesitate to quickly detach from it for several reasons ("...sailing away in the dark"). Found this after reading up a bit on the topic.
Mother and baby are just referring to the Cutty Sark (mother, larger) and the Gypsy Moth IV (baby, being much smaller). They were next to each other at one point, perhaps they still are.