Start small and cheap learning to sail and all the other things associated with boat ownership...then after a couple of seasons if you find you actually use it and can afford it, go as big and expensive as you comfortably can. It worked for us, and I'm so glad we didn't mess around and jumped from a 20' $400 boat to our current one.
Tartan 37 - S/V Windgeist
Sailing the Chesapeake Bay
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Photo by Joe McCary