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Sailing's important because blowing up ships (or running away from ships depending on how good of a shot you are) is probably the most fun thing to do in the game, especially when you have or are part of a crew (I would say playing poker is up there as well, but I didn't get far enough in Phase 1 to find out what its like to gain exp in poker).
Also, once Phase 2 is up running long enough, the Cuban Gang will, in all probability, go back to their bullying ways. So, its important to have a high enough level in sailing to protect yourself from them, right!? And the fastest way to level up sailing is to sail with a guild.
This isn't to take away from gaining experience with the pistol, cutlass, dagger, voodoo, etc. But I believe sailing within in a guild is the heart and soul of the game.
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If you have to be at work at 8, it's always like, 7:54. Just enough time to do nothing. To just lay there and go, "I can't do anything! I can't even have an English muffin!" - Dane Cook
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