Wow, didn't realize Scottevest came in other than black. The flourescent yellow would definitely get some attention at sea, but I'll probably order the olive.

I'm thinking though that even the Scottevest windbreaker might be a tad warm for the Caribbean even at night. It would be a good place to stash those yellow dimes, but I'd still go with the RailRiders VersaTac Ultra Light pants .

The roomy pockets in the RailRider pants would make a great tier-1 and the Scottevest windbreaker would be a great tier-2 (referring to the "1st/2nd/3rd line of gear" concept).
For the drills and any possible incidents involving lifeboats, I'd leave the bag with your tier-3 in your room. It will get in your way and there are better ways to carry stuff for those occasions.

Lifeboat drills and things going exactly as planned aside, I always looked at abandon ship evolutions with the possibility of having to swim -- YMMV

$.02

I wonder if they'd let me bring my own flotation vest...
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Better is the Enemy of Good Enough.
Okay, what’s your point??