Grace - if you need to work to make a living, be sure to research the local jobs situation before you decide on a place to live. I lived in Key Largo for years, and that is, in my opinion, by far the best place in Florida to keep a sailboat because there is great sailing locally, it's easy to get to and from the Bahamas, and the diving, snorkling, fishing, etc. is awesome. The drawback is that there is virtually no work unless you wait tables, work on a dive boat, or clean rooms in one of the hotels.....
The Miami and Ft. Lauderdale areas are incredibly congested on land and on the water, and they are the most expensive places to keep a boat. Ft. Pierce is great, the Merritt Island / Port Canaveral area is good, and most of the towns on the west coast from Tampa south to Naples are great places to live and sail as well.
Also - check out Craigslist as a source for dockage in the areas you are interested in. You can find some great deals there on slips at small marinas or at private residences.
1981 Endeavour 32
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"At sea, I learned how little a person needs, not how much." Robin Lee Graham