You'll have to decide (& tell us) what kind of climate, & shore based support/amenities you're thinking of. As one man's simple is another's "Big City", & vice versa.
Ditto on how much you desire to be able to harbor hop, even if you choose not to do so. Plus, what, if any, culture & language barriers you're up for dealing with. And how often your boat needs complex parts
, meaning ones of the sort which can't be had locally.