The Overseas Railroad that carried Hemingway to Key West in 1934
Over the holidays I was reading a new book that explores the period in famed author Ernest Hemingway’s life when he owned the fishing boat Pilar. The first few chapters of Hemingway’s Boat are dedicated to his purchase of the boat upon his return to the US after a three-month African hunting safari and his subsequent trip to Key West, Florida where he would settle for the next several years.
Hemingway’s trip to Key West included traversing the Overseas Railroad, an engineering marvel that is celebrating its 100th anniversary later this month. Although not a commercial success for developer Henry Flagler, the Overseas Railroad did provide the backbone for what would become one of the most exciting road trip destinations in the world; the Overseas Highway.
Stretching 127.5 miles from Homestead, FL to Key West, the Overseas Highway cuts a southwestern path through the Gulf of Mexico connecting the dots that make up the Florida Keys. Most of the highway is built over water making for a spectacular journey, unless there happens to be a hurricane (which caused the demise of the original railroad).
According to Hemingway’s Boat, Hemingway’s journey originated in New York City on April 9th, 1934 and included a stopover in Philadelphia where he met with officials of the Academy of Natural Sciences who were interested in his knowledge of Gulf Stream fish, before terminating two days later at the southernmost point of the continental US. Upon his arrival to Key West, also known as the Conch Republic, Hemingway was met by a marching band as his celebrity had already been established.
If you’re looking for a great southern escape this winter, you may want to follow Hemingway and head down to Key West for a tropical vacation that’s still within the borders of the US. Although you can no longer take the train (the railroad was decommission after damage done by the Labor Day Hurricane of 1935) you can drive the entire distance and use Cost2Drive.com to help plan for the trip. Another option is to fly to Miami and rent a car as its a three-hour drive from Miami to Key West and well worth the trip. Below is in interactive map that plots out the route and highlights key stops along the way.
Happy Driving!
Cost2Go Blog 
Ahhh, the drive to Key West. So incredible. Between Florida City and Key Largo, I take Card Sound Road in one direction and stick to US1 the other. Much different experiences.
Happy New Year!
Cool. Will have to try that on the next trip.