I don't get the surfboard part. I've never cruised on a 50-foot sailboat, but I have owned a 30-footer and crewed on a 45-foot offshore sailboat, and I used to go to multiple sailboat shows every year to ogle the boats I'd never be able to afford. I cannot imagine bringing a surfboard on a sailboat that size for an extended cruise.
Surfboards/kayaks are actually pretty common. In Santa Barbara, there were fewer boats without those on board than with. All the urchin divers, lobster guys, etc. would bring their boards on the little 22'-29' Radons that are so popular there. That was 2-4 boards per boat. Sailboats have a bit less deck room, but even stuff like the Catalina 25s would have a surfboard or kayak tied down somewhere.