A Florida Keys trip is one road. The Overseas Highway runs south from the mainland through Key Largo, Islamorada and the lower Keys, and it ends in Key West. So the easiest way to plan is in the order you drive it. Every guide we have written for the Keys is below, top of the road to the bottom.
We have snorkeled and dived the reef at John Pennekamp and spent time on boats in the Keys. That drive is what these guides are built around.
Plan the whole Florida Keys trip first
Start with the Miami to Key West road trip itinerary. It lays the drive out over three days, with stops and costs. Then use the guides below for each stop.
Before you leave Miami
Most Keys trips start with a flight into Miami. The Miami weekend itinerary covers two days in the city, and the Everglades day trip is the other big outing from town. For a beach before the drive, see Virginia Key, Key Biscayne and Matheson Hammock.
Key Largo and Islamorada
The upper Keys come first. John Pennekamp snorkeling covers what a reef trip costs and what to book. If you are choosing where to sleep the first night, Key Largo vs Islamorada compares the two.
The lower Keys
Bahia Honda State Park is the beach stop on the way down. The guide covers fees, camping and which of its beaches to pick.
Key West and the Dry Tortugas
The road ends in Key West. See the things to do in Key West guide for a short trip. From there, the Dry Tortugas day trip goes out by boat or seaplane, and it is worth booking early.
Leaving from PortMiami instead
If your Florida Keys trip ends on a cruise ship, read the PortMiami cruise parking guide and the cruise packing list before you go.