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There is a way to get a ladder before the pirate, but I doubt people do it much. Get Tungsten ore from the Caveling Oasis in the desert caves.
Ooooh if that's possible, then I'll do it. In fact I already have a Tungsten anvil and Tungsten pickaxe from farming Caveling Oasis, though it took me around 7-8 oasis to get that much tungsten ore, lolz. But yeah, I don't mind grinding, if it will result in me having better gear. Thanks!
After reading the wiki for a long time, my plan was to get Tungsten pickaxe from farming Caveling Oasis, go to Deep Snow cave and get Glacial ore, craft a Glacial pickaxe, then go to Deep Swamp caves, get Mycelium ore and craft my complete Mycelium armour set as I am playing summoner, and then finally go fight the Pirate King.
Ok I took all my settlers and they killed the Pirate Captain before I could even inflict any damage on him, lolzzz.
Also, the Ice Pickaxe found in deep snow cave chests is the best pickaxe in the game.
But other than that the achievement were introduced later, people also play multiplayer where some people defeat the captain and others just enter the caves :)