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The Curse of Monkey Island Hints
How do I get in the windmill?
1 of 6: Your first step actually isn't getting in the windmill. (This should only be a puzzle in Mega-Monkey mode.)
2 of 6: Just try to get on top of it.
3 of 6: Those blades might carry you.
4 of 6: Just find an item that will let you hook yourself on.
5 of 6: An umbrella might be nice.
6 of 6: Order a drink with an umbrella from Goodsoup at the bar. You can use that umbrella (it's full-sized) on the blades to get on top of the windmill.