In Hemingway’s “To Have and Have Not,” the protagonist Harry Morgan, a contraband runner between the Florida Keys and Cuba, foretells the future of Key West. “What they’re trying to do,” he says, “is starve you Conchs out of here so they can burn down the shacks and put up apartments and make this a tourist town.”
“You talk like a radical,” his friend replies.
When Hemingway was writing “To Have and Have Not” in the ’30s, he was living with his second wife Phoebe in a rickety two-story with lime-green shutters, within walking distance of Sloppy Joe’s bar on Key West’s Duval Street. There was once a boxing ring behind the house, but while he was in Spain with his correspondent mistress (later wife number three), Phoebe replaced it with a massive swimming pool, the biggest on the island. She filled it with salt water because there was no freshwater available, then paid the price by scraping algae off the pool’s side every few days.
The radical may have been right. When Hemingway was in Key West the place was rough, outback-y, fishermen and sailors elbowing the stray wealthy speculator for room at the bars. Today his house is open for tourists who peer into his bed and his bookshelves (Thomas Mann and Proust and forgotten adventure novels) and kneel down to pet the 40 cats, all descendants of Snowball, the cat Hemingway’s son Jack clings to in a photo on the wall. Families with babies elbow college-aged Spring Breakers and stickered senior tour groups for room on Duval Street, the island’s main drag, and on the cramped manmade beaches, all in anxious pursuit of warmth and of fun. “Welcome to paradise,” said the concierge as he handed us our keys.
“I’ll go anywhere warm,” I’d told my mom from my dorm room in Cambridge, sleet beating the windows, wind whistling over the Charles. Left to her own devices, I should have learned by now, she would invariably plan a vacation with, one, a road trip and, two, archetypal Americana. So we rented a red Mustang in Miami and drove down to Isla Morada, where the nicest restaurant boasts a winking mermaid on its sign, and then through the strip malls and RV Resorts, over the seven-mile bridge (vertigo in the middle, when you can’t see where you’re going or where you’ve been), to the southernmost city in the continental United States.
“This is your country,” my mom told me, as she had at Illinois’ Corn Palace, at Graceland, at Mount Rushmore. This she repeated, encouragingly, as we passed the Hard Rock Café with cocktailed 20-somethings hanging off the balcony, as we walked through the dock for the nightly sunset festival where enterprising salesmen had packed the boardwalk with snacks, magicians, guitarists strumming James Taylor, and tarot card readers. The sunset itself was its own side show.
There were characters now, as there were in Hemingway’s day, though instead of rummys and smugglers they’d become drag show hosts and tour guides. How Key West evolved from wilderness to tackiness: There’s a book Hemingway never had the chance to write.
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