Bob Steel has a lot to say about what makes the Classic Yacht Regatta special, and none of it is about trophies.
The owner of Impeccable, a regular on the classics circuit, is full of praise for the community that gathers around these older boats.

The regatta splits its fleet into two groups. Classics are any yacht launched before 1976 that has competed in a Sydney Hobart Yacht Race. Modern Classics cover yachts launched after 1975 but before 1996, with the same Sydney Hobart requirement.
That eligibility rule matters. It ties every boat in the fleet back to the race itself, so these aren't simply old yachts dressed up for a parade. Each one has a genuine Hobart pedigree.