Stay at the City Dock in Naples, fuel dock, restaurant and close to a ride if you need it. Key West is 108 miles from Naples, add 5 miles to Stock Island Village Marina. If you can cruise at 25 mph you'll get to KW in about 5 hours. Check the sea conditions at Smith Shoal Light before you leave Naples. Smith Shoal light area will kick ass if the winds are over 15/20 mph from any direction. What is your range and fuel burn? When you leave Panama City are you going to Steinhatchie? The Sea Hag is a ok marina, not much else around there. If your going to Carrabelle there is a decent marina there, but no restaurant. I live in both Naples and Key West. Let me know if I can help.