Untether and Drift into Key West

• Tweet

• Tweet

Over the years, Key West, Florida, has been threatened by the rising tides of commercialization and corporatization. 
 However, the eccentric and fiercely independent people of the island have managed to do a reputable job staving off the rising tides of American cultural homogeneity, as well as the corporate jets.  Key West floats in the middle of the Caribbean, like the shining high beam of a lighthouse, beckoning all the bohemians, free thinkers, writers, pleasure seekers, artists and freaks to come and enjoy her land, where all are welcome, weirdness reigns and nobody ever wants to leave.

Besides the obvious fact that the island floats in the middle of the Caribbean and is completely detached from the United States (aside from a lengthy stretch of road called U.S. 1), Key West couldn’t be any more diametrically different than “the mainland”, as some of the locals refer to it.

Because Key West has mostly staved off the unavoidable creep of vapid, Florida strip mall culture, it maintains a gritty, freewheeling vibe.  Imagine a place that simultaneously charms you with its open mindedness and aesthetic beauty, but encourages you cut anchor and leave your everyday sensibilities in Davey Jones locker.  Oh, and in the middle of all that, there’s a circus sideshow too.

Mallory Square is always a tourist favorite, as it’s the congregating point for all the local street performers and weirdoes during the sunset ceremony.  People seem to enjoy The Cat Man and the one guy who should be known as The Tumbler.  The Tumbler does a phenomenal show running around, jumping, leaping, summersaulting and of course, tumbling, all on concrete with no cushion.

The other tourist mainstays are of course the Hemingway House, which is a worthwhile visit that tips the hat to one of our cultural legends and best writers.  The tourist circuit also includes a trip to Mel Fischer’s Maritime Museum to see the gold, silver, precious stones and jewelry from the Spanish wreck Atocha.  Finally some people with an affinity for parrots might want to go to Jimmy Buffet’s.  For others who don’t enjoy cheeseburgers in paradise, the better place to go is right across Fleming Street to La Concha hotel.  Go to the roof for a couple of boat drinks while enjoying a sunset and some live music.  Make sure you dedicate a quality chunk of time to exploring the more authentic nooks and crannies of the island.

If the tourist circuit makes you want to walk the plank, then before you uncover the island’s most authentic treasures, head off to Fort Zachary Taylor State Park.  You won’t miss much if you choose to skip checking out the old fort and ramparts; just head directly to the majestic beach.  Basking in the sun and lounging on a Caribbean beach has some indescribable, intangible magic and you’ll find it here in abundance.  Swim, snorkel, bodyboard, fish, and shell until your fingers are so pruned you can’t feel them, but you won’t care because you’re in Shangri La.  If you’re lucky, you might even catch one of the most beautiful nature shows possible.  At this tip of the island, the quicker moving currents of the Atlantic meet the calmer Caribbean streams and collide, forming a turbulent, fierce mash of fast moving water.  Here you can sometimes spot a pod of dolphins surfing the waves and riding the currents, and playing carefree in paradise.  After a day at the beach, the doctors of Key West would highly recommend a night of play in town.

Start out with dinner at El Siboney, a delicious, cozy Cuban restaurant far off the beat tourist track.  If you’re looking for a chic, elegant spot for a candlelit dinner don’t come here.  If you’re looking for an authentic taste of Key West and want to enjoy some of the best Cuban food you’ll ever lay lips on, then go to El Siboney.  It’s a homely type of place you feel like grandma and grandpa are still overseeing.  The best place to eat is at the counter.  Not only do you get faster service, but it’s highly likely some local Conchs will strike up a conversation with you.  So it’s like dinner and a show!  And of course, you know that wherever locals eat, is the right place to be.  Thirsty you say?  Key West provides refreshments, even though your thirst never seems quite quenched.

Walk up and down Duval Street and you’ll find a watering hole to your liking.  Visit the iconic Bull & Whistle, but be careful upstairs in Eden if you’re not an exhibitionist.  For a couple of great, non-touristy bars go to Schooner Wharf or The Green Parrot.  Schooner Wharf feels very much like a 300 year old schooner that never needs renovating because it’s perfect as it is- worn, weathered and full of character.  The Green Parrot is frequented by locals and offers live music, walls filled with memorable folk art and stiff drinks.  Try to make it out to Duval St. around 9 p.m. to see resident James Chapman ride his bike.  His bike lights up like the Rockefeller Center Christmas Tree and he jams Rick James and Ray Charles from a stereo system he has mounted on the bike, as he casually peddles along.  You’ll be dancing and partying behind him likes it’s 1999.  Have a hangover in the morning?  Got you covered.

Go to the Southernmost Beach Café on Sunday morning for their build your own Bloody Mary bar.  Nothing says good morning on Key West like beach, bright sun and the bite of 9 a.m. vodka and tabasco.  If you’re still reeling after breakfast, do some exploring and find Nancy Forrester’s Secret Garden, it’s a quaint, tropical garden in the middle of town next to a bird sanctuary where you can see parrots and macaws.  The shade and solace here will melt your hangover away.  From here, get over to the Key West Cemetery.  You’ll see some quirky and quite dark humor here in the unforgettable epitaphs of some of the island’s most famous residents.  Hungry?  Go around the corner from the cemetery and hit 5 Brothers Grocery store.  They have the best Cuban sandwiches on the island.

Finally, if you’re ready to hit the bar again and you love craft beer, go to The Porch on Duval Street.  It’s one of the only bars that has air conditioning on the strip.  The bar sits slightly elevated on the corner which provides excellent people watching below, not to mention one of the best microbrew selections on the island.  Whatever you do with your time in Key West, just be sure to enjoy one of America’s most walkable cities, get to know some of the locals and live in a way you never knew was possible.  Then you’ll feel like a Conch.

Daniel Pott is Author at PrivateJetsCharter.com, where travel is Tailor Made.