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Help!! Florida sailing?
Troy, I can offer you some observations on Charlotte Harbor and the W coast of Florida, FWIW - which won''t be much, since this is such a personal thing.
We owned a condo in the PG/PC area and, while the bay is a wonderful resource to local sailors (tho with much shallow water), the town has always struck us as provincial and uninteresting, with the Snowbird enclaves sequestered and not really part of the community. (Please remember, these are just personal reactions we''ve had to the area...). The undeveloped bordering lands to the estuary were purchased by the State of Florida several decades ago - finally, Florida took some steps to preserve a small piece of its natural beauty - which promises little change for the future from a sailing perspective. You have multiple passes both N and S of the area, offering protected motoring up/down the ICW or alongshore passages of varying lengths. The water from Venice (to the N) down to Ft. Myers is quite attractive, much moreso than further north.
We ended up being far more attracted to the Tampa Bay area, which has a nice collection of larger cities AND small towns, plus a nearby ''critical mass'' that provides more entertainment, employment (I realize, not your concern), skilled trades and the other infrastructure that makes life pleasant and easy. There is local cruising both on the Bay and somewhat N and certainly S of it. I''d encourage you to include this area in your consideration; if smaller towns are your desire, consider Ruskin, Palmetto and Bradenton in your review.
Good luck on the search...