Join Date: Nov 2002
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Are you looking to spend time on the boat, or just daysail? A 25'-27' boat most likely means you will need a slip to keep it in, so you're not just looking at the price of a boat, but a place to keep it as well...summer and winter. If you have a vehicle you can tow with, you might want to look smaller, something that you can rig easily and by yourself.
You could also look around at the marina's and yacht clubs in your area for crewing opportunities and get some more experience before you make an investment in a boat.
There's no one "right" way to start. All you can really do is ask for advice, then choose what is right for you.