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The Curse of Monkey Island Hints
How do I win in ship-to-ship combat?
1 of 5: First of all, you need to find a well-matched opponent. The stronger pirates have cannons with longer ranges, so they're harder to fight.
2 of 5: In order of increasing difficulty, the pirates are Not Really Fearsome Pirates, Semi-Fearsome Pirates, Mildly Fearsome Pirates, Pretty Fearsome Pirates, Fearsome Pirates, Really Fearsome Pirates, and Captain Rottingham.
3 of 5: Start with the easier pirates and work your way up. You can take the treasure you win and cash it in at Puerto Pollo for better weapons, which then allows you to fight stronger pirates, etc. There are a total of 7 strengths of cannon -- which seem to match the different levels of opponents as well.
4 of 5: I recommend trading up your cannons after each you defeat each pirate both in ship-to-ship and sword combat. That way, your hold will always be empty if you lose to a pirate in a sword fight. Each victory entitles you to one upgrade.
5 of 5: If you still have trouble, try to keep your side to your opponent, and flee whenever his side is to yours. If that still doesn't work, talk to Haggis and tell him you want the crew to help you. You can then defeat a ship with a single hit.