Long before Rum Runners were cooling off thirsty tourists in the Keys, pirates thirsting for other treasure sailed the coastal waters. The Florida Keys are known for their laid-back vibe with an emphasis on fun, and our tour, the annual week-long bicycle tour of the Keys, fits right in. The scenery is incredible, and the short riding days provide plenty of time to sample the varied cuisine, dip a toe or more into the turquoise water, swim with dolphins or kayak a secluded shoreline.
Most of the bicycling is on the Florida Keys Overseas Heritage Bike Trail, separate from cars but never far from the action – stunning ocean vistas sometimes populated with glimpses of dolphins, sharks, turtles, manatees, egrets, herons and the ubiquitous, oddly shaped brown pelicans.
The sounds of live music, clinking glasses and laughter spill out the open doors of countless Duval Street bars, hinting at the good times to be had inside. Mallory Square hosts the biggest nightly sunset party in the Keys, a multi-ring circus of flame jugglers, tightrope-walking dogs, Houdini-like escape artists and more, all vying for your attention with a steady comedic patter.
The Keys were discovered and charted in 1513 by Spaniard Ponce de Leon, best known for his search for the Fountain of Youth. De Leon thought the Fountain was never found, but he was wrong – it’s everywhere in the Keys, a destination that will have you peeling off the years like so many layers of unnecessary clothing.
The Spanish wrecked many a ship on the reefs looking for gold, those wrecks ultimately becoming treasure for scuba divers and marine life. The Spanish called these chains of islands “keys,” from the Spanish word “cayos,” which means “small islands.”
Florida became U.S. territory in 1812, with settlers first arriving in Key West in 1822. Pirates still prowled the waters then, so the Navy established a special fleet tasked with controlling the buccaneers. Early residents found rich fishing grounds and some even grew rich salvaging shipwrecks.
When early entrepreneur Henry Flagler decided to run a railroad the length of the Keys, it got the islands on track and chugging toward the future. Enamored of south Florida and its potential, Flagler started work on the 156-mile Over-Sea Railroad in 1905. The last section was laid in 1912 and Flagler, one of the original partners in Standard Oil and a hotel magnate, spent a week celebrating the completion with Key West locals.
To visitors, it appears the celebration never stopped. Key West remains a magical place of spectacular sunsets and unparalleled nightlife. The same is true for all the other islands.
Florida Keys ride is really more a vacation than a normal bike tour. The Florida Keys are beautiful and offer a variety of non-biking activities. Swim with the dolphins. Snorkel. Dive. Key Deer. Deep Sea Fishing. Museums. Conch Fritters. Key Lime Pie.
The Seven Mile Bridge just might be the most beautiful seven miles you have ever biked.