Our party installed a gigantic narwhal-esque horn/ram to the front and named it The Checkered Fang.
My players have dubbed their ship Freedom's Toll, in honor of their fallen comrades.
So far our ships are The Defiant Wyrmling, The Twilight Blaze, The Rapscallion and The Likely Story.
We love coming up with names and flags for them!
My party named the Man's Promise the Grindilow Hunter, by the captains orders
The second ship they got, I was allowed control of it, and it was first named the Drunken Hippo, but due to the GM allowing us to RP with the NPC's alot, my characters friendship with Owlbear and relationship with Sandra caused me to rename it Sandra's Owlbear
Our group rechristened the Man's Promise as The Lacedon, after our Juju Oracle took control of one of the lacedons in the fight with the gridyilow queen.
My group named their first ship: The Dignity Destroyer
Their second ship was named: It's a diversion
Their third was named: The lylith
I forgot the name of their last ship, at that point we reached the ''spelljammer'' moment of the campaign, and the end.
Kat's Grace, simple, elegant and extremely haunted.
My parties very first ship was just christened 'The Devilfish' yesterday after a good bit of the session was spent coming up with one. It was almost the DareDevilfish (the DareDevil DD on the flag and everything), but the GM warned that names considered stupid would be met with a sinking, and we weren't sure if that crossed the line.
Our party shaman knows a pretty good artist that owes him a favor, so we'll be having our own colors drawn up, involving a skull and seven purple, hooked tentacles on a black background.
Went through it twice...
First go-around, it was The Dancing Lady,in honor of a drunken(?) vision our cleric had of Desna.
Second time, it was the Hagfish- ugly, incomprehensible, and yet strangely effective.
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They went through several options when trying to decide but ultimately decided on my suggestion after I told them the story of how Odysseus escaped the cyclops Polythemus so The Truewind, which they acquired before even getting to Rickety Squibs, is named Nemo. This is also partially because at Rickety Squib's the workers had a tradition of toasting ships they were working on by saying, "Cheers to the Yet to be Named," which is what they wanted to call it.
They plan to name the next ship they actually have crew to pilot Skirtchaser in honor of their captain.
My Players ship is the Leviathan, and there flag is the Hydra symbol.
For my crew, a bunch of Sodden Land survivors led by a Sodden Land fallen Paladin turned pirate, we ended up renaming our current 3 ships as follows:
The Man's Promise has become 'Sodders Luck'
The Chelish Dominator has become 'Abrogail's Lacking Bosom' (Usually Truncated to, ironically, 'The Wench-Queen', the Figure head being the Original Chelish Queen figurehead, with the clothing re-carved into something more suitable)
And a slaver ship we captured while heading to the Squibs has ended up as 'The Hangman's Oath', because we hung the last Captain from the Mainmast and our ex-Paladin has promised to do the same to any cheeky type that pretends to surrender and then draws weapons afterwards on us again.