Join Date: Nov 2005
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My advice would be to go look at local boats in your price range. On this budget your selection is limited to what is for sale in your area. You may find out that you can't afford what you are looking for or you may find out that you don't like what you see and need to wait for more boats to come on the market.
Pretty much any boat in the 20-25 foot range will allow you to sail yourself and also sail with a couple of other people.
Just look what's available, what you can afford and then research those boats. You will learn a lot about boats by researching. Most likely you will buy the wrong boat, but that's part of the learning process and the "right boat" is probably not available at your price range. The wrong boat will most likely be good enough for a few years or maybe even forever. Most boats in this price range will be in need of repair. I advise you to buy the boat in the best condition as they pretty much can all day sail. If you are looking to do overnights >25% of the time, then pay attention to the accommodations for that. Don't look for a boat that will or can "do it all" because you won't find it.