Arrr! Ya make me think I be wantin' to reprise the roll of me own pirate captain, Masan-Ru! He don't waste his time in pirate-speak like me, but he be a masterstroke of a man to contend with!
Apart from that, it becomes necessary to know the kind of encounter you'd be up for. Going down the list...
Garlock The Destroyer would protend to be an ordinary cat - which he is VERY not - around his crew for funsies.
Akbar The Third might be a victim of some plundering that would probably try to get him to pay for the goods by following and attacking him.
Gary Blight would probably engage in a case of co-working and attempts at robbery, because he is perhaps the greatest thieving goblin in the world.
Rena Goldswith might've been hired to take him in IF he's notorious enough.
Sano and Travis are unavailable and you REALLY don't want Valis, because he'll kill him, probably.
Keefe Zarla might be on board because she needs a boat to get to someone she wants to assassinate, but...I can't think of who because people off of the main continent don't affect said continent.
Fuzzy is...an extremely dangerous rabbit who I'd LIKE to have appear in random threads, but I'd have to justify it.
Kate is not likely to be involved unless Jack's getting involved in Connlaoth and cannons, or because for some reason he needs an innovative genius for something.