I'll take a crack at the definition, Nutsy:

Cruising is a many meaning term:
It can mean servicing on a Naval warship for a definite passage.
It can mean booking passage on a vessel with a Captain, Crew, Stewards,
Cooks etc for a fixed price;
Could mean doing a task in an easy manner (Cruising thru it)

As I said it is a very broad term and can be used in many, many ways.
The way it is being used in this discussion is to define a wanderer,
moving from place to place for a period of time without need of
external aid to survive in comfort and pleasure. A very loose feeling
of restrictive activity allowing the ability to do various things while
using a sailing craft.

So there; Mr Webster, Ole Thom as spoken; AND well you know!

Ole Thom