Try bringing multiple grass rafts or boat patches incase your boat starts sinking, I'd also recommend looking at the wiki to see what buffs the gems give and find the best combination. I also bet you could find a pretty good walk through of the fight if you just search it up on youtube.
I'm playing as vanilla Wendy and what worked for me against pearled ck was using purple gems (he gets to around 12k hp which isn't much, and the sleep immunity from gems is irrelevant since Abigail will be taking care of the crabbies).
I open the fight by killing the claws first, then smacking him until he starts pushing me back which I counter by rowing, then if I'm pushed near a tower, I smack it down, if not, beeline towards ck while Abby controls the crabby guys, she will be damaged a lot by them so have a specter cure all active at all times.
When the ice breaks and new claws spawn, i row a bit to take down one maybe two towers while the claws group up, when they are all together, I set Abby to aggressive which usually takes care of them for a while leaving a window open to damage ck again.
As for boat health, usually I repair mine with a board when I'm being pushed, and fix holes with a kit, but that's just my way, you may find more success just using grass rafts and a pan flute with gems other than purple, keep in mind though, that both wikis are outdated right now so the gem effects are inaccurate for the reworked fight.
Try bringing multiple grass rafts or boat patches incase your boat starts sinking, I'd also recommend looking at the wiki to see what buffs the gems give and find the best combination. I also bet you could find a pretty good walk through of the fight if you just search it up on youtube.
I'm playing as vanilla Wendy and what worked for me against pearled ck was using purple gems (he gets to around 12k hp which isn't much, and the sleep immunity from gems is irrelevant since Abigail will be taking care of the crabbies). I open the fight by killing the claws first, then smacking him until he starts pushing me back which I counter by rowing, then if I'm pushed near a tower, I smack it down, if not, beeline towards ck while Abby controls the crabby guys, she will be damaged a lot by them so have a specter cure all active at all times. When the ice breaks and new claws spawn, i row a bit to take down one maybe two towers while the claws group up, when they are all together, I set Abby to aggressive which usually takes care of them for a while leaving a window open to damage ck again. As for boat health, usually I repair mine with a board when I'm being pushed, and fix holes with a kit, but that's just my way, you may find more success just using grass rafts and a pan flute with gems other than purple, keep in mind though, that both wikis are outdated right now so the gem effects are inaccurate for the reworked fight.
Several on YouTube.