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Go to a local sailing club, there'll be a course offered where you bomb around in a Laser or something similar to learn the basics.
Me personally, after doing that course I would buy myself a small boat (something you can spend a couple nights aboard) and start touring around; probably try and take an experienced person with me the first few times), making sure you have a good motor incase shit hits the fan. And start learning maps and charts.
I'm not a sailor in any way whatsoever but I have the same goal/dream as you.
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'16 Ram 1500
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