Fay made its first landfall in Florida at Key West also on August 18 winds were at 60 mph . The next day Fay made landfall in Cape Romano , Florida while winds were at 65 mph . Fay made four Florida landfalls , first at Key West in the late afternoon of August 18 , then early the following morning at Cape Romano south of Naples as a 65 mph ( 100 km\/h ) tropical storm .