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
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
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.
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
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.