Here's some suggestions I have from spending time on the hook in the Keys. Marathon - has a big harbor with marinas. Food and shopping within walking distance. There are a few public ramps on Marathon and a good protected one behind the airport on the bank side. I launch there and leave my car with trailer there for several days without issues. If you want a waterfront room there try the Seahorse Motel. They have a ramp and your boat is docked 15' behind your room in a protected canal. It's located at the south end of the Marathon airport but not enough flights to make noise problems. Rental cars are had at the airport. You may want to stop at Looe Key on the way down and do some snorkeling. They have mooring buoys. Many species of fish and coral heads. Swimming depths are from 30' on the edge to 3' in the center. Newfound Harbor - has plenty of room and draft for big and small sailboats. Bahai Honda State Park - nice anchorage off the beach on the banks side. They also have a marina with limited supplies. Saddlebunch Key near Sugerloaf Key - There's a nice surge free anchorage for small boats just inside before you get to the US1 bridge. It's a few miles before Key West on the Atlantic side. When in Key West you can anchor off the Holiday Inn that is on the bank side just as US1 turns right on to the island. This HI also has a big parking lot for boat trailers. We stayed there in a waterfront room and anchored a Catalina 22 off the beach from the room. Summer rates were $125 nite for 4 people. This is a budget motel in Key West...closer to town it is 3x the cost while you still have to pay to dock and there is no trailer space. The city marina is just down the road and has an excellent ramp, but masts have to go down to get in there. Bill P.