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I've been able to swim out from Padres. Go down to the dock nearest the shipwright, jump in, and swim toward the rock in that same direction. You should eventually be able to swim out to sea, but it takes forever to get anywhere that way. I'd try swimming from places it's not likely anyone will just swim out to. Like toward the back of an island or way off to the sides. Kind of like looking for dig spots. The 'holes' that let you through to the high seas are going to be in out of the way places.
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