First, let me say that I wish we all had problems like how to bike to work in comfort in Waikiki like TheRCF.
As to the subject of discomfort, I'll say my 33-mile ride last summer down Haleakala (okay, I know that's a different island) was very comfortable on a rented Navigator 400. I wore my Mt. Borah MTB baggies that have an unpadded lycra liner, actually made for recumbent riders like myself. (I don't wish to preach this except to say my short wheel-base recumbent fits on my home city's buses Sportracks without a problem.)
I have friends that rave about their SPD sandals, but I still prefer MTB shoes myself - can't get used to the open toe look, even on my recumbent.
Anyway, check out the Mt. Borah shorts.
Now, how to carry a surfboard, I've no idea....
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I'll gently rise and I'll softly call
Good night and joy be with you all.