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I fucking love sailing.
I crew on an XP-33, pic semi-related (not this exact boat).
But yeah, if people are interested in sailing then you've got two real options:
>Crew on a keelboat (free, but might be harder to find a team)
>Buy a dinghy (will cost a couple thousand)
Just start with a Pacer or something. You can get them for practically nothing and they're the perfect boat to learn on.