KEY WEST, Florida — In his epic ballad “Key West (Philosopher Pirate),” Bob Dylan sings that Key West is “fine and fair” and also “paradise divine.”
I’m not one to argue.
We followed his advice. We stayed “on the road” and followed “the highway sign.” We stayed “to the left and then you lean to the right.”
The only advice I’m less sure of is, “If you lost your mind you’ll find it there.” No doubt, we found something there.
The road to Key West is an attraction itself
The “Overseas Highway” is one of the most remarkable stretches of road in the country. The highway was built upon the Florida East Coast Railway’s Key West Extension right-of-way, the former Overseas Railroad.
The railroad was heavily damaged by the 1935 Labor Day hurricane and wasn’t rebuilt; Florida later purchased the right-of-way. Much of the route was subsequently expanded and paralleled by more modern structures; much of the original right-of-way lives on as a walking trail.
The highway has many pull-offs where travelers can inspect the original road’s engineering marvels: its varied bridges, the most impressive of which is arguably the Seven Mile Bridge. The new Seven Mile Bridge that opened in 1982 is roughly 6.8 miles long.
Explore the history
Key West has a fascinating and deep history that begins with the aforementioned Overseas Highway and extends to the city’s saloons.
Perhaps the city’s most famous resident, Ernest Hemingway, called Key West home in the 1930s. Visitors can trace his footsteps, starting with the Ernest Hemingway House, which the author called home from 1931 to 1939.
Anyone looking for more of the island’s history might consider a visit to Fort Zachary Taylor Historic State Park, a Civil War-era fort on the island’s southern end, or the Harry S. Truman Little White House, which President Harry S Truman used as the winter White House, staying a total of 175 days during 11 visits.
Don’t forget to frequent the legendary watering holes
While in town, Hemingway enjoyed local watering holes, and two prominent places top the list: Capt Tony’s Saloon and Sloppy Joe’s.
Anyone looking to combine history with craft brews should check out First Flight Island Restaurant & Brewery. Aside from serving quality brews and laying claim to the southernmost brewery in the United States, First Flight is housed in the birthplace of Pan American World Airways, and the airline sold its first tickets out of the building in 1927.
Of course, there are several options around Mallory Square, the perfect place to imbibe on a cold one while watching the sunset.
After sundown, check out LaTeDa, a hotel with a restaurant worth exploring. It’s a popular venue for a Key West institution, The Fabulous Spectrelles.
Spend time on — or above — the water
It’s probably fair to say the water is the biggest draw for many visitors to Key West. Anyone looking to enjoy the water around Key West from above should consider taking a seaplane to Dry Tortugas National Park.
The snorkeling at the park is a nice escape from the Key West hubbub. It’s also interesting to ponder the history of Fort Jefferson at the park and its role in our nation’s defense during the early days.
