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Hint One: You have to do three different things help Guybrush get one step closer to 1st place.
Hint Two: You will need something to help you spit farther, a little bit of cheating, and help from nature.
Hint Three: You will need a drink to make your spit thick
find a way to move the flags closer to the line while everyone is distracted
and spit when the wind is blowing
Solution: You need to move the flags by using the ship horn and picking up the flags when the crowd looks away, use the green drink from the bartender on Scabb island to make your spit thick (Combine Yellow Beard's Baby and Blue Whale), and then wait until the wind blows on the red sash that the woman at the end of the line is wearing.