Reporting back.
I was able to successfully climb up out of the water when the boat was docked in Freeport. I did as recommended and headed for the mast at which point I was transferred up to the deck of the boat.
I jumped off and tried again, approaching the boat head-on. This time as soon as I contacted the outer shell of the boat I got pulled up into the bow of the ship, but was stuck and unable to move. Once the boat started moving, I poofed onto the middle of the boat, above decks and was again fine to move around.
So.. confirmed this works
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