Don't know much about Florida's West Coast but seems like previous posters have provided good info. Have done the east Coast route from Key West to St.Augustine many times, both inside and outside. Several marinas in KW. All fairly expensive. We always stay at the Galleon, inside the Bight and close to restaurants. Groceries in KW are not close. Nice run and when conditions are right (can't do it if a North wind is blowing) it's a great sailing day in the Hawk Channel from KW to Marathon where you can anchor or stay at the very good Marathon Marina. From there, again great sailing opportunity going towards Miami. You'll need to check info from others on anchoring possibilities or marinas up that leg as we always go straight through.
Approaching Miami, you might have to go outside if you mast is higher than the 56 feet posted clearance of Tuttle bridge. We stay outside to Fort Lauderdale. Lots of marinas to choose from there. South of Lauderdale in the ICW you can anchor in Hollywood Lake. North of Sunrise bridge in Lauderdale is the small Sunrise lake where you can anchor overnight.
If you stay inside the ICW there are a few places to anchor along the way. The bridges will slow you down but it's a nice motor trip that will show you lots of beautiful nature scenes. Sailing outside along the coast from Port Everglades (Lauderdale), the inlet at Lake Worth provides a good access 24 hours a day and there are 2 places for anchoring + marinas. From Lake Worth, for a sail boat, the next 24 hours inlet is Fort Pierce. Again marinas and anchorage near the inlet. FYI it's 84 miles from Port Everglades to Fort Pierce with Lake Worth about half way.
From Fort Pierce going north, Port Canaveral is your next inlet (good marinas, no anchorage unless you go up the Barge Canal towards the Indian river), followed by Ponce Inlet, then St.Augustine, St.John River (Jacksonville is about 18 miles up river), and St-Mary's.
Inside you'll find Vero Beach, with good marina and excellent free bus service for provisioning, then good anchoring near marker 21, next going towards Melbourne and Cocoa there are lots of places for anchoring. Cocoa provides free internet, charming old town next to the anchorage and good bus service to shopping mall, Walmart and West Marine. North of that is Titusville with good marinas, anchoring and mooring facilities.
If you stay inside, New Smyrna has marinas, of course Daytona offers all kinds of docking space as well as some anchoring. Someone already told you about St. Augustine. Plenty of mooring and marinas. Great restaurants.
From there, because of the meanderingand shoaling of the ICW we always run outside to St.Mary's.
If you do plan that trip allowing enough time so as to not to rush & giving yourself the time to maybe wait for the favorible weather window, you should have a great and very enjoyable trip. Good luck and be safe ! Claude