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On my first pirate, I did grenades last. MAN I wish someone had told me to master grenades first. (Actually, I think several people did, but I just didn't get it.) On every subsequent pirate, I make a very serious effort to master grenades as soon as possible, since it was so unbelievably miserable, the first time around.
Once grenades are level 25, you can visit Joshamee Gibbs and start the Black Pearl quest or even start grinding on other weapons. But if you don't do grenades and only grenades first, you'll be very sorry later.
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