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Old enough to know better
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In your price range I think the above is best. There are some truly ocean capable trailer sailors, like the Northsea. But they are likely triple you budget and are not a "lightweight" trailer boat and will take a pretty good truck to pull. Several have circumnavigated the globe so quite seaworthy. One thing to keep in mind even if they are on a trailer it is not quite like a power boat, you have to step the mast and what not. If you find one that the previous owner sailed from the trailer it may be set up with a gin poll and what not. Figure an hour at least for the first year to put up the mast and another to pull it down. At least from what I have seen on friends boats. If you keep it at a marina or club you may be able to leave the mast up in the lot and just drop it in the water. Makes life easier. You may also have the option to stay at a dock or mooring ball when you want.
 
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