This is a really open ended request. There are just too many choices.
I could argue to decide what you will tolerate on the following and go from there:
What is you limit for cold/hot weather?
What is your tolerance for crowds?
What is your tolerance for high costs?
Is live aboard a must?
Answering those will be a start. Just the liveaboard one will narrow things significantly, and if that's a requirement, will there be any dirt home?
Most of the boating in the US is done on either coast or inland rivers, with a fair amount on the south east coast (gulf). So you can probably start there. Now, you could go to Alaska, too, as an option. The folks that live in those areas (especially if they've lived elsewhere) can give you good comments.
My experience is pretty much limited to the west coast of Florida, but lived and boated in the midwest for awhile, too. The goods of Florida: weather, good boating, reasonable costs. The bads of Florida: weather (hurricanes, tornados) expensive and CROWDS. My biggest complaint here is the crowds and in increased costs above the cost of living index.
The original question needs to be narrowed a LOT.
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PS... unrelated: What do my posts come out with double spaces between paragraphs? Don't write that way.