What a contrast the two ideas, The Compleat Cruiser(Rosinante' sliver), and the more recent idea of cruising(ala Cruising World) your photo depicts.

No resemblance, really. Plus L Francis Herreshoff enjoyed a more pristine southern NE waterway, sort of like parts of coastal Maine today.

One idea is about whisping along on a tidal creek, the other, moving your floating home from place to place. The ideas have different priorities that are hard to combine.

David Bruckman in his pieces, Fetching Along in Points East comes the closest to bringing the two ideas together. My pleasure leans toward his idea of cruising, but I wouldn't take his beloved LEIGHT down the ICW.