Things to think about
This is a campaign full of pirates, with pirate themes everywhere. It might be best to have a pirate theme about the way you think and play. You will be on a ship for months on end. You will encounter different times where food will be what you can cook and what you have on you, or what you can find. You will be dealing with dirty merchants and crafty salesmen, not to mention a few liars. It may pay well to have some “connections” of the underground variety. Sometimes merchants may appraise poorly, or may lie all together.
Sailing will be a daily occurrence, but don’t forget about your other requirements as well. Certain roles will need to be filled if you don’t hire crew to perform these duties. Yes, fixing a ship might be mostly done with magic, but knowing what to fix in certain situations might require a shipwright. A Navigator will keep you on course, but unless you spring for a indoor crows nest the maps might be subject to wind. Want some fish? Better have a good cook who knows what is and isn’t poisonous. If you choose to use a crew, the morale of your crew will be something you must keep a handle on. You wouldn’t want a mutiny to leave you stranded on the open seas.
A small boat will get you where you need to go, and sometimes be easier to hide in plain sight, but might not fit all the plunder you require. A larger boat will mean more ways to split the plunder you receive to keep the crew happy. If they see you taking all of it and only giving them a pittance, they may not take too kindly to it.
Of course, there are other ways to keep a boat going…