Re: who knows about sailing and sailboats?
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There must be a broker around that you can go to and they can show you around. There are plenty of used boats to choose from to fit into your price range. If the boat is used, ask someone to recommend a surveyor that will inspect it for you before you buy.
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The surveyor thing is key. However you may want to consider crewing out of, or even joining one of your local yacht clubs. You may find that you can satisfy your jones by just being crew for a while. If you still want to own you will have a network of really knowlegeable sailors to give you advice.
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I did this a lot when I was a teenager. I crewed all over the place. There's always someone looking to move a boat from place to place or who's regular crew is sick or something, that just needs an extra set of hands. They usually pay for food, beer and a little extra. Just hang around the docks or marina bars on weekends and meet the regulars.
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