Tom, Here's my list of cool spots in the area you'll be cruising. Number one is Cumberland Island, a days sail south of St. Simon. Only the folks on the
ferry and anyone taking their own boat are on the 17 mile long National park. We always stay for a couple days. Downtown Fernandina is cool. Good anchorage and the city muni has a
cheap dinghy dock. Good restaurants. Off the
ICW south of Amelia Island is the Kingsley Plantation. Swift currents, check your set at tide change.
Anchor in the deep water channel, tide range is around 9 feet. If you want to
work on your
hull, anchor to the north east and you'll be high and dry at low tide on a sandbar. Look for Caps On The Water before you get to St. Augustine. Great lunch spot with dockage. St. Augustine is a must. Again, the city muni has a good
dinghy dock, but you need to pick up a
mooring ball or use one of the slips. Great town. Eat at the Floridian. The city of Cocoa has a free dock for day use. If its full, anchor off and run your dink in (lock it up). Lots of good places to eat, our favorite is Ossorio. Vero Beach muni has a
mooring field. You can run your dink up through the houses to get to a grocery store on A1A. Stuart is nice, they have a mooring field, but we never stay there. We always anchor in Peck Lake for a couple days. Great anchorage and the last sane place in South
Florida until you leave
Miami in your wake.
Lake Worth has a good anchorage. Drop hook on the north end, dink in (again, lock up your dink) and hit Publix for provisions. They also used to have a tap outside for cruisers to fill up jerry cans. Lake Boca Raton is a good place to drop hook. The park at the north west side gives you access to the city to provision or just grab a bit to eat. Avoid this pond on the weekend, it gets crazy. No Name Harbor at the end of Key Biscane is a lot of fun. Bike to the lighthouse or eat at the Boaters
Grill on the harbor. Great protection, but crazy on the weekend.
Key Largo is great for
provisioning. On Plantation Key there's a Yacht Harbor Resort with great protection, but the BEST part is the county park with an Olympic sized swimming pool next door. A stop in Marathon's Boot Key is a must. The muni has a mooring field and dinghy dock. Find a restaurant called Keys Fishery and order the lobster Reuben.
Bahia Honda has a great state park and a cool little port (two, actually). Great snorkeling. Key West is Key West. Remember, everything in moderation. Find the guy selling
fish from the back of his pickup (assuming you know how to pick fresh fish) for the cheapest and best
food in Key West. If in season, buy fresh Firecracker shrimp. If you can, go to Garden Key for a few days. No provisions are available, so stock up. Fort Jefferson is great, and at night you have the place to yourself (and any campers). The staff tends to stay in their quarters.
So, Cumberland and the Dry Tortugas bookend the tour, and they are our favorite places.
Good luck!