The problem is: What is the best hat to wear for cat sailing?

"Best" is always, to one degree or another, subject to personal preference. I for example think the Original Hobie 18 is the "Best" Cat, altho there are many here that would disagree. But hey, I won't come to your front door and try to convert you either.

That having been said, MY favorite sailing hat is an old cycling hat. You remember them? The short brimmed cloth hats that cyclists used to wear before they all switched over to helmets.

The are not all that easy to find anymore because cyclists, both professional and recreational have almost universally gone to wearing helmets.

The one I wear is several years old and my significant other has had to patch it and put new elastic in it but it is still my absolute favorite.

One of my old sailing buddies used to prefer an old railroad engineers hat for the same reason I like the cycling hat, the small brim that is easily turned up so that you don't have tilt your head back so far to see all the way up the mast when looking at the sail.

I've tried using a "do rag" and it works well for improving the upward sight line, but it also provides NO protection from the sun for the rest of my face.

Anyway, there's a couple of thoughts for all ya'll to consider.

Stephen