Darby Drydock

[MissMarple]

Hmmm. Seems to me that I had to buy my first ship, a light sloop and it cost $100. Once purchased you can name it. Then IIRC you need to go to the NPC on the dock that the Harbormaster stands in front of and he tells you how to sail it.
O f course, I could have dreamt all this while I was in jail !!!!

[owensar]

press TAB, and then click ships and launch while in water.

[crystalseeker]

I had two of those problems. First, I couldn't get the ship and then the dock character never told me how to sail (when I finally created another character). I roamed around Port Royal what seemed like forever (arg, those crabs). Finally I discovered that I could get to Tortuga by using the Map (move it by dragging the mouse).