I'd agree wiht Jotun. The sailing club is an easy and CHEAP way to get into sailing. Also 99.9% of what you learn there is applicable to larger boats, especially as smaller dinghies make you much more aware of boat trim and sail trim, and how the boat is affected by it.
Most good big boat racers started as small boat racers first. Look at Paul Cayard, from the Volvo Open 70 boat, Pirates of the Caribbean, and how well he has done. He started in Lasers many years ago.
You should also get some time in at an ASA-certified school and get a bareboat cruising qualification from them. Once you've done that, save your money and then when you have a vacation, get a bunch of friends together and charter a boat.
It is also helpful if you find some like-minded friends, who are also willing to get ASA-qualified for bareboat charters.
Some of us were lucky enough to grow up on the seacoast and got our sailing on both freshwater and saltwater growing up.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.