I'm a watch guy too, and while I'll wear whatever I happen to be wearing that day sailing (it is, after all, just a watch, and my philosophy is that if all it's going to do is sit in a watch box and never be worn then it's useless), on an extended cruise where I'd be away from home for a long while I'd only bring two -
my quartz Luminox, simply because it's built like a friggin tank, is extremely accurate, and the luminous dials are mighty convenient at night..
and my "automatik" Sinn 556, because frankly I'm completely in love with it and it's a "dressier" watch to wear when making landfall.. Plus, it looks stunning in person and I love the attention it gets from the women despite its incredibly simple dial
Other than that, other watches that have made it onto a boat are an Omega Seamaster 120, old Gruen military watch, Glycine Airman, Swatch Chrono, and countless cheapies.. I've lost a Fortis Flieger Chrono over the side though (bummer!), so some crab off the coast of Brittany is sporting that one.. and I got so pissed off at the Seiko automatic and it's ridiculous 6-8 hr power reserve and chronic inaccuracy (granted it was a cheapie) that I voluntarily offered that one up to Neptune two years ago off the coast of Maine after it made an escape attempt by snapping one of the spring-bars and falling onto the cockpit sole.
But yeah, all that to say - it's a watch -wear what you like and what you're comfortable wearing for extended periods of time. And don't wear anything you're not prepared to lose or replace.