It is important for Jerry to swim through the tunnel, on a literal level, because he wants to be able to fit in with the older, local boys who could do it. These boys seemed "like men to Jerry," and when they came to the wild bay, he wanted nothing more than to be accepted by them. Initially, the boys made room for him, but once they began to swim through the tunnel, he clowned around to get their attention, and they abandoned him. In Jerry's eyes, what really separates him from them is their ability to perform this physical feat. He longs to close the gap between himself and these older boys by erasing this difference.
On a symbolic level, Jerry wants to swim through the tunnel because he longs to grow up. Swimming through the tunnel feels like an initiation of sorts, as if accomplishing this task will prove, somehow, that he's ready for adulthood.
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