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Sailing only for retirees?
A lot of this depends on what you do for a living and how comfortable you want to be. I did this for a little while when I was in College. I had bought an old boat, fixed her up and basically camped aboard. I worked in boat yards and also parking cars evenings and weekends when I need a little extra cash. I pretty easily covered my expenses. I drove an old junker automobile and did a lot of my own work. It all worked quite well.
I anchored out in the ''pirates'' off of Dinner Key which was a popular but not terribly protected anchorage. I did not have an engine and so rowed my Folkboat in and tied to the seawall with the dinghies just like many a non-powered boats of that era. I am sure its is all a lot more regulated today.
Jeff
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