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Where do you want (can) cruise?
Staying in the USA or the Bahamas does not require a bigger boat as your supplies are closer and easier to get.
When do you want to go?
Would you like to get some experience first and then move up to a bigger boat?
There is many 26 to 30 footers that can get you out of the dock for the price range that you mentioned. You can resell if you want to get a bigger boat after a season of getting your keel wet. Plus you get to go now. With most of the time below in the bunk anyway, it might be better.
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