Your goal should be to be someplace secure by September. Very high chance of named storms.
Two choices: up the Keys and along the Everglades or across
Florida Bay.
If you go along the 'Glades keep tethered in so the mosquitoes don't carry you off. I've never gone that
route.
Directly from
Key West depends on how fast you go. Closest stops are Marco Island or Naples, about 90 nm. Next up the coast is
Fort Myers Beach at 120 nm. Good
mooring field and many
marinas, restaurants etc. all accessible by
boat or
dinghy.
From there you can go up the
ICW to Cabbage Key/Boca Grande (about 20 mn) or outside and in at Boca Grande Pass.
Charlotte Harbor and Punta Gorda are up the Bay.
Back outside is Venice with the Crows Nest Restaurant and Marina just inside.
Current can be very strong and the channel in (red right returning) becomes ICW (red towards the mainland) at the first turn.
Sarasota is next but tricky to find the Big Pass entrance coming from the South. New Pass is the other way in: it has been dredged in the last year or so. Inside is Marina Jack, a
mooring field and Sanibel. Also Longboat Key Moorings on the West side of the Bay. High end resort if you need to unwind.
Tampa Bay is next, whether in-or-outside. South side has Bradenton Beach and Cortez on the ICW, Bradenton is around the corner and up the river.
St Petersberg or Gulfport Municipal
marinas or the Harborage would be my choices in the Bay. Skipping Tampa Bay Clearwater would be next place to stop. Last place is Tarpon Springs and its' Greek sponge
fishing heritage.
Can't help you from there north except that the
water is very skinny a long ways out with long narrow channels.
My best
advice would be to go to the
Dry Tortugas while you're in the Keys. I would spend a week there then leave from there for the
West Coast. But that's me.
Watch out for crab/lobster pots in
Florida Bay and all along the coast.
Have a great time.