Celebrim
Legend
And, of course, this brings up another point. Age of Piracy era is pretty anachronistic for D&D. We're talking several centuries ahead of what D&D is typically pegged at.
D&D is conceptually pegged at Medieval.
In practice, Gygaxian D&D is Victorian minus gunpowder. Age of Piracy is actually anachronistic the other way in many cases.
It's not really obvious because the medieval era is so far away historically that unless one actually reads primary sources from that era one probably has only vague notions about it. What ones notions are probably set by is actually literature about the medieval era or movies based on that literature. And that's something like "Ivanhoe" which was published in 1820, and where Gygax gets so many of his own anachronisms from (chainmail, longsword, etc.) I knew some of this already - the typical D&D city is London from Oliver Twist - but it really got hammered home emotionally for me when I read an article about costuming in Disney Princess movies, and for the most part they are visually set in the 19th century.
If you have a Crow's Nest on your ships, you are set AFTER the real Golden Age of Piracy. That wasn't invented until the late 18th century.
And modern D&D (say 5e) is actually later than that in many cases, conceptually the 1880s sans some gunpowder and a bit of anachronistic costuming at times. Only Eberron actually leaned into that, but D&D has become this self-referential thing that is defining its own genre and its very not based on the Middle Ages in any way.
If you keep to Medieval (say 1400 (ish) (yes, yes, I KNOW that's not right, but, it's a decent rough number, sit down in the back) level technology, then the ships are a LOT smaller and easier to work with in the game. Crews of 5-10 aren't unreasonable at all for most of these ships, which means you can have the PC's plus a nice, manageable number of NPC's on the ship. I would recommend keeping things lower technology, especially since you're not likely to be using cannons and gunpowder anyway.
Except that real medieval pirates aren't using sailing vessels. They are using the same vessels that dominated piracy for the prior 2000 years - rowed galleys. Whether its Viking longships with their high freeboard and clinker built construction for the open Atlantic or Mediterranean galleys that would have been recognizable to ancient Greeks, pirates in this era are taking advantage of the galley's "sprint speed" to ambush and chase down the clumsy cogs and ships of this era, often relying on the fact they can go against the wind and the prey ship will be blown inexorably into their path. In other words, a pirate campaign that is really medieval doesn't look anything like what people picture when they think pirates. And, on top of that, the crews aren't smaller, they are larger. Indeed, even into the age of criminal pirates like Blackbeard, this tactic of cramming hundreds of cuthroats onto a rowed ship and sprinting to ambush sailing vessels was still in use. It was actually more in use by pirates than cannon fire. But it won't feel like "pirates' to someone raised on "Pirates of the Caribbean" or even (it is hoped) "The Sea Hawk" and "Captain Blood".