Winner Best Travel Book
Finalist Best Graphic Design
Best Book Awards
Winner Excellence in Craft, Florida Outdoor
dreamy, impulsive, unpredictable, utopian, visionary, wanderer
... Here is where people go when they can suddenly take no more of insincere smiles, collared shirts and frozen roads. When they wake up one morning and instead of brewing a cup of coffee, they start driving. Driving until the car breaks down or they run out of gas, and then they hitchhike, and walk, and crawl if necessary. Losing possessions along the way. Items once so dear, now just baggage. Winter coats, lost relationships, forgotten dreams and underwear scattered in their wake. With each mile, the weight in their hearts growing slightly lighter. With each step, more conviction. With each breath, more hope, more warmth. An awakened, rejuvenated spirit. Until they finally reach the end of the road.
Here. The Florida Keys. The great box of misfit toys.
Not all those who wander are lost...
but sometimes they are.
The roosters have already been crowing for awhile when the sun’s first rays spill down Duval. As the air warms, the town begins to unfold peacefully. First a jogger. Efficient and tidy strides. Focused and driven. He looks like a well-rested fellow who enjoyed a comfortable bed last night.
Next, a homeless man pushes his bicycle. Einstein hair, a clutter of chaotic belongings dangling from the seat and handlebars. He is engrossed in self conversation. He looks like he slept decently, albeit outside under the mangroves.
A deafening roar temporarily interrupts the tranquility as a city worker pilots his street-sweeper. The truck lumbers by, indifferently consuming the evidence from last night’s festivities. Plastic cups, Mardi Gras beads and pizza crusts all gobbled up in its wake, leaving the gutters, and inhabitants, with a fresh start for a new day.
Soon, a few hungover-looking hotel guests begin to emerge, seeking breakfast and coffee. A trim woman bicycling in yoga shorts turns heads. One too many heads. An exhausted-looking man lugging multiple suitcases receives a vigorous verbal retribution from his girlfriend.
Other folks dock their dinghies after a night sleeping on their boats “on the hook.” A few shop owners unlock front doors. A dog stops to check messages on the fire hydrant. And a clean-cut young man, barefoot with disheveled hair staggers by. He stops.
“Excuse me,” he asks in very broken English. “Do you know where is my hotel?”
“What is the name of your hotel?” We ask.
“Can remember, no. My hotel is. On a street.”
“Hmm, which street?”
“Street with... hotels.” He looks down at his feet, searching for a memory and realizing the pointlessness of the conversation.
Or maybe he was just wondering where his shoes had disappeared to. At least it was warm out.
This was not a surprising situation — that fact that it was warm out, and that there was a shoeless man who couldn’t find his hotel. A number of people, like this fellow, pay good money for a perfectly nice hotel room only to wake up under a tree or in an alley. In their defense, through inebriated eyes these places can look like splendid spots to curl up for the night.
The young fellow looks up from his grimy, liberated feet, cracks an embarrassed half smile as if to say thanks for having this conversation, turns and shuffles off, slowly, to enjoy his day.
Hotels, Motels, Cottages, Inns, B&Bs, Camping and Boats
Casa Marina: With a lobby and promenade straight out the The Great Gatsby, two pools by the ocean and the largest private beach on the island, Casa Marina is indisputably the grand old hotel of Key West. Fish from a private pier, spa it up or nap in a beach
hammock. Dare to get really classy by donning your velvet smoking jacket and heading to the outside bar for a sip of a mojito, a puff of hand-rolled cigar and an unobstructed view of yoga classes. A Waldorf Astoria property. Family friendly. casamarinaresort.com, 1500 Reynolds Street, 888-303-5719 reservations, 305-296-3535 local.
Eden House: From cheapo to swanky, this collection of conch houses and art deco space blends cost, convenience, funk and style. The exuberant social scene starts with a free check-in beer and continues in the tropical courtyard with guest barbecues,
hammocks, a sun deck, jacuzzi and happy hour at the heated pool. For seclusion, book a tranquil apartment suite with a private porch swing and outdoor bamboo shower. Those on a budget, or just in need of a place for sleep, can book a tiny single or a Euro-house-style space with shared bathrooms. Rooms have wi-fi and air conditioning, but intentionally lack alarm clocks and phones. Family friendly. edenhouse.com, 1015 Fleming Street, 800-533-5397, 305-296-6868.
Seashell Motel & Key West Hostel: Leading the competition for the most expensive
10-bunk dorm room hostel in the world, the Key West Hostel is still cheaper than a tent camping site anywhere in the Lower Keys. Choose from segregated or co-ed dorm rooms, or lay down the Benjamins for one of the private, modest hotel rooms. But the wi-fi, communal kitchen and coin-op laundry come free!
Except for the price of the coins, of course. keywesthostel.com, 718 South Street, 305-296-5719.
Culture & History
Hemingway House was home to Ernest, and is now the casa for 50 or so six-toed cats, the first in-ground swimming pool in Key West, and Hemingway’s “last penny.” For those who like Hemingway’s work or mutant felines, this should be a pilgrimage destination. For dog people, or those who don’t care much about the writer, you will probably be better off spending your entrance fee on a bottle of the Hemingway-inspired Papa’s Pilar rum. hemingwayhome.com, 907 Whitehead Street, 305-294-1136.
Playwright Tennessee Williams lived in Key West from the 40s to 80s, and wrote some of his notable works here. He had a house here too, but admirers can only walk by the front, as it is currently a private residence. To tour Williams history here, walk by the house at 1431 Duncan Street, visit an exhibit dedicated to him at 513 Truman Ave., 305-842-1666, and catch a play or movie at his namesake theater at the Florida Keys Community College, 5901 College Road, Stock Island, 305-296-1520.
Robert Frost spent 16 winters in Key West at his cottage at 410 Caroline Street, which is also home to one of the first wells to provide drinking water to the town. Later, his place became a museum, which closed in 2010. It was reborn as a cottage, inhabited by some free-spirited artists and musicians. But as Frost once put it, “Progress goes on visibly around us mounting from savagery to barbarianism to civilization to sophistication to decadence and so to destruction.” Appropriately the cycle continues. His cottage now houses a real estate office.
The popular Sloppy Joe’s Bar is home to the annual Hemingway look-alike contest. He often planted his cheeks at Sloppy Joe's, both at its current location as well its former address across the street at the present-day Capt. Tony's Bar. Rumor has it he built his house by the lighthouse so no matter how drunk he got, he just had to focus on walking toward the light. It’s not recommended to try that today, as buildings and trees now block the path. What is recommended is trying to impress a member of the opposite sex by throwing a quarter into the mouth of the plaster grouper (large fish) above the entrance to Captain Tony’s, while people at the Mexican restaurant across the street make fun of your talents.