Think about that… just seven years to build the railroad system, about 139 miles, mostly through wetlands and over water, more than 100 years ago with limited heavy equipment like we have today.  
When the railroad made access to Islamorada from the mainland easier, many people traveled to Islamorada to fish and enjoy the tropical climate of the Florida Keys: the beginning of the tourist industry, over 100 years ago.


The Overseas Highway: Another major effort that impacted travel to and from the Florida Keys was the highway. In about 1908, the people of Islamorada petitioned Monroe County.  They wanted a road! There were only a few families that lived on Upper Matecumbe: the Pinders, the Russells, and the Parkers made up most of the population back then. Upper Matecumbe was densely wooded, almost a jungle. To get from one settlement on the island to another, the residents would usually travel by boat, walk the beach, or once the railroad was built, walk along the railroad track.
Finally, in 1926 Monroe County began the requested road on Upper Matecumbe, known as the Overseas Motor Highway. Amazingly, by November 1927, just over a year later, it was possible to travel from Miami to the far end of Lower Matecumbe by car. Once car travel was possible to Lower Matecumbe, the county approved the use of ferries from Lower Matecumbe to No Name Key, 40 miles away. With the use of the ferries, by the beginning of 1928, it was possible to drive from Miami to Key West. 
During the Great Depression in the 1930s, the government was unable to pay the promised bonuses to World War I veterans. Franklin Delano Roosevelt was president and with help from Congress, he formed the Works Progress Administration to do public works projects, including the construction of public buildings and roads, creating jobs and putting people back to work. One of the projects was to build sections of the Overseas Highway in order to eliminate the need for the ferries.
In November 1934, the Federal government sent almost 600 veterans to the Keys to build bridges, quarry stone and build a school. Some of the veterans were to create a bridge across Channel Two at the south end of Lower Matecumbe. The veterans were working on that project when the Labor Day hurricane of 1935 struck Islamorada.  
There are still lower sections of the piers the veterans had been building, visible out in Florida Bay at the far end of Lower Matecumbe.


The 1935 Hurricane: On September 2, Labor Day, those 600 veterans of World War I had nowhere to shelter as a major hurricane approached. An emergency train was sent but it arrived too late. The storm hit with an 18-foot storm surge and 200 MPH winds. Almost 500 people died that night, including many veterans as well as local residents. 
The Florida East Coast Railway track had many sections missing from Snake Creek to Marathon. The days of the railroad running through the Keys were over. The right-of-way from Florida City to Key West was sold to the Overseas Road and Toll Bridge District for $640,000. 
The railway right-of-way and more than 40 bridges were converted into a highway, with extensions on the sides of nearly all the bridges to make them just wide enough to accommodate two-way traffic. Unlike other bridges on the Oversea Railway, the Bahia Honda Bridge, at MM37, had steel truss construction. This was a necessary difference from the predominate concrete arch form of the other bridges of the Overseas Railroad, as the channel is the deepest of those spanned, at 24 feet deep. The central span is 247 feet. Because the existing deck inside the truss was too narrow for two lane vehicular traffic, the top of the structure was re-decked for use as a second lane of the Overseas Highway. The bridge served as the primary mode of transportation to the Lower Keys and as the main evacuation route until it was replaced by a four-lane bridge in 1980, along with all the other historic railway bridges.
In March of 1938, less than three years after the Labor Day storm of 1935, 139 miles of roadway became part of U.S. 1. And no ferries were needed to get to Key West. A toll booth was erected at the far end of Lower Matecumbe to collect $1 for car and driver and another $.25 per passenger. In 1953, Monroe County residents were issued windshield stickers and could travel without the toll. In 1954, the road became completely toll free. 

So yes, there is a history of tolls on US One in the Keys. And yes, a history where a brand new road was designed and built, 139 miles long, in less time that it has taken to complete the permanent repairs to the highway damage by Sea Oats Beach caused by Hurricane Irma in September of 2017.