Re: I've never sailed in my life... talk me into it.
Really now, stego, you can't just run out and buy a sailboat the way you can buy a powerboat.
Sailing, more properly known as yachting, is an elitist sport and you have to be invited to participate. You'll need written letters of sponsorship from three respected sailors (for each of you) and be prepared to buy a round of drinks for everyone in the room when the committee discusses your sponsorship. While Topsiders are no longer required, you be expected to wear proper attire, as specified in the rule book.
Now, once you've been sponsored, you can show up at any sailing school and enroll for classes. You'll be given two chances to pass the exams, if you fail, your sponsorship will be cancelled and there is no pro-rated rebate on your membership dues. You'll have to wait a full two years before you can re-apply.
This may seem unfair, but really, it is the only way to keep the thronging masses from cluttering up the anchorages and putting wall-to-wall boats on the waters.
No, really... (VBG)
But I'd strongly suggest a US Power Squadrons or USCGAuxiliary boating safety class (usually ~$40 and one short day) which will get you an insurance discount on your boat and a quick introduction to safety, and to local boaters. Followed by a basic sailing class9es) because they'll bring you up to speed on how to "do it right" way faster than any other way. And again, introduce you to other local sailors.
Racing can be an exercise in TypeA personalities and the avoidance thereof, but it is also something every sailor should try. When you need bbq supplies and the supermarket in the next town is an hour away from closing, knowing how to get there quickly is a valuable skill. :-)