Florida Keys & Key West
If Florida is a state apart from the USA, the Keys are islands apart from Florida – in other words, it's different down here. They march to the beat of their own drum, or Alabama country band, or Jimmy Buffett single, or Bahamanian steel calypso set... This is a place where those who reject everyday life on the mainland escape.
The Keys, like any frontier, have always been defined by two ‘E’s’: edge and eccentric. And when it came to the far frontier, the very edge, the last outpost of America – out here, only the most eccentric would dare venture. And thus, Key West: the most beautifully strange (or is it strangely beautiful?) island in the US. This place is seriously screwy, in a (mostly) good way.
Key Largo & Tavernier
We ain’t gonna lie: Key Largo (both the name of the town and the island it’s on) is slightly underwhelming at a glance. ‘Under’ is the key word, as its main sights are under the water, rather than above. As you drive onto the islands, Key Largo resembles a long line of low-lying hammock and strip development.
Islamorada (eye-luh-murr-ah-da) is also known as ‘The Village of Islands.’ Doesn’t that sound pretty? Well, it really is. This little string of pearls (well, keys) – Plantation, Upper and Lower Matecumbe, Shell and Lignumvitae (lignum-vite-ee) – shimmers as one of the prettiest stretches of the islands.
Calle Ocho, in Miami’s Little Havana happens to be the eastern end of the Tamiami Trail/US 41, which cuts through the Everglades to the Gulf of Mexico. So go west, young traveler, along US 41, a few dozen miles and several different worlds away from the city where the heat is on.
Marathon sits right on the halfway point between Key Largo and Key West, and it's a good place to stop on a road trip across the islands. It’s perhaps the most ‘developed’ key outside Key West (that’s really pushing the definition of the word ‘developed’) in the sense that it has large shopping centers and a population of a few thousand.
Big Pine, Bahia Honda & Looe Key
Big Pine is home to endless stretches of quiet roads, Key West employees who found a way around astronomical real-estate rates, and packs of wandering Key deer. Bahia Honda has everyone’s favorite sandy beach, while the coral-reef system of Looe offers amazing reef-diving opportunities.
The end of the track is an old Florida fishing village of raised houses, turquoise water and scattershot emerald-green mangrove islands. Hwy 29 runs south through town into the peaceful residential island of Chokoloskee, past a great psychedelic mural of a gator on a shed.