Thanks for the suggestions and answers provided.

I'll say it again, though, for some for which it wasn't clear:

I am sailing for 8 weeks through 20+ islands - its almost a mini-sabbatical rather than a simple week or 2 trip. This is the only reason I'm bringing (not considering to bring, but absolutely bringing, additional equipment.) I am amused at some of the comments about what I should and shouldn't bring! It's simply not a matter of if, but how, I should do this.

In the end, I may simply revert to checked luggage, though, generally a 3rd checked item is $150 and 4th item is $200 so I do really appreciate the alternatives suggested! And the issue is not the cost as much as the risk of it being on hand when I get to my boat. I am taking 2 days of my trip simply to prep the boat. So, please keep the ideas coming - thanks!

(Did I make it clear that I am living aboard for 8 weeks and that I'm bringing certain gear??) Thanks!