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Thanks for the advice!

Really interesting material; it has a lot of potential as a PS. However, there's way too much "telling" and not enough "showing." If you want the reader to be involved and to appreciate your experiences, you must put them in your shoes; it needs to be a story, not a recounting of events. Part of the problem may be that you have so much to discuss (you certainly have done/been involved in some interesting things), which can be remedied by cutting the essay down to just a handful of key experiences and elaborating on only those.

Also, "unique" is a taboo word in PS's--it's beaten to death because so many people use it.

I think you have a very interesting backstory but a very uninteresting PS. I agree with DreamShake's comment about showing rather than telling. I would add that I think you shouldn't even go into this much depth about your career. If I were you, I would pick a sailing story from your childhood, a time when you a life lesson encapsulated in something you learned from sailing, and write about that.

If you're going to make this be "why law school," then you need to come up with a better explanation. I mean, being out on the sea in international water must have exposed you to complex legal issues. Just say you developed an interest in maritime law and leave it at that.

Couldn't read. Too jealous that you have a boat.

As a first draft, this is a good start. As a near final draft, it is not as well written or as well organized as it should be for a final draft resulting in a predictable, somewhat boring narrative. The weakness comes from the final two paragraphs. Consider rewriting them or just deleting them.

Thanks for your help everybody. I do appreciate your suggestions, which are similar to the concerns that I had and still have. When I spoke to the admissions director at my target school he advised me to write about the diversity of my experiences aboard the yachts and how that work experience shaped me.

I also realize that it is easy to think my family must have been wealthy in order to afford a boat. The reality is that we sold our house and car in order to afford it and lived very frugally aboard it for 4 years in a living space not much bigger than a small kitchen. The upside to that was growing up in the tropics, which I will never complain about!