when we lived in Naples, we took the trip several times. The only real purpose I saw in the trip was avoiding 7 hours of driving to Key West and back. I don't think I would use it for a day trip. The best part of Key West is the night life and if you don't stay the night then you miss out on the point of going to Key West.
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Lexington, Ky Charleston, SC Indianapolis, IN Naples, FL The Villages
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