Three hours into my latest visit to Key West, Fla., I listened as a mermaid explained why islanders are called “Conchs.”
“We had a tradition a long time ago where, when a baby was born — because, back then, your baby was born at home — you would put a stick in the yard and put a conch shell on it. That’s how you knew there was a new Conch born.”
A second-generation Conch, Kristi Ann Mills — known locally as Mermaid Kristi Ann — runs the annual Key West Mermaid Festival. She and I met on a previous visit and I think of her as representing what’s best about Key West: the people.
Renowned for stray chickens in the roads, bender-encouraging dive bars and the laid-back “Margaritaville” lifestyle popularized by Jimmy Buffett, Key West has long attracted a bohemian blend of artists, musicians, conservationists and dropouts to the end-of-the-road tropics at the southernmost tip of the United States.
During the pandemic, the island became a different sort of haven, beckoning an influx of newcomers seeking an outdoor lifestyle. Real estate prices soared and with Florida’s open tourism policy, the hotel business boomed.
So, could I, a thrifty traveler, still enjoy it?
Over a San Pellegrino ($2.95) at the Funky Rooster Coffee House and Wine Bar in Old Town, where a “pet bar,” or water bowl on the porch, had a sign reading “Dogs and chickens drink for free,” Ms. Mills assured me I could. She shared her tips for favorite places — many of which I visited — and introduced me to other passionate Conchs who make the place unique.
“Go off track,” she advised. “You’ll see how we do things a little differently.”
Rooms and bikes for rent
In October, a relatively quiet month to visit Key West, bargain accommodations were running about $175 a night and up. At NYAH — short for Not Your Average Hotel — a bed in a quad dorm room with a private bathroom was going for $100 a night. It was a compelling offer, especially since the hostel — a series of connected cottages — maintains courtyard pools, includes breakfast (covered by the roughly $10 a night resort fee) and is centrally located in Old Town.
Unless you’re reserving a private room with family or friends, staying at a hostel risks mystery roommates. In this case, the only other woman sharing the no-frills room had strewed her clothes across all four bunks and explained that she was binge partying after a breakup. Fortunately, since she’d come home at 5 a.m. and I’d head out by 8 a.m., we rarely overlapped during my two-night stay.
Early morning was my favorite time to cycle around Key West. I had arranged to rent a single-speed cruiser through Eaton Bikes, which offers a 10 percent discount on advance reservations made online (the two-day rental cost $28.80). Thanks to the company’s contactless delivery service, I found the locked bike parked at NYAH’s racks before I arrived and would leave it in the same place upon departure for pickup.
A popular way to get around the island, biking beats walking for speed and range, and avoids the frustration in this no-street-parking place of having to try to park a car in packed lots or on restricted streets.
Most often, I stuck to lightly trafficked residential routes, pedalling past Conch shacks with profuse greenery and brightly painted hurricane shutters that provided a dazzling D.I.Y. architecture tour with every ride.
Historic wealth and ‘vulgar T-shirts’
Amid the simpler homes lie impressive mansions — many of them converted to bed and breakfasts or museums — that provide a key clue to the island’s past: In the 1830’s, Key West was the richest city per capita in the United States.
“One hundred years later, Key West was so poor, people forgot that,” said Thomas Greenwood, the curator at the Oldest House Museum and Garden (admission $10), noting that Key West was also the first city to declare bankruptcy in the Depression. “Now they remember us for our vulgar T-shirts and our cheap beer.”
I met Mr. Greenwood at the relatively modest 1829 Bahamian-style, wood-framed house with a dormer roof and raised porch on the main drag, Duval Street. It is filled with antiques from the earliest period when the family of Francis Watlington, a sea captain, harbor master and state legislator, resided here, including a game table set with 19th-century pasteboard playing cards. Behind it, Spanish lime and gumbo limbo trees shade a cookhouse in the garden, a tranquil spot just steps from Duval, which was teeming with passengers from the giant Carnival Glory cruise ship. The ship was in port for the day at a private dock that has controversially been allowed to host them, despite a 2020 vote to curtail cruise ships.
I followed the crowds about six blocks to perhaps the island’s best-known mansion, the Hemingway Home and Museum (admission $18), where the author Ernest Hemingway resided from 1931 to 1939 with his second wife, Pauline Pfeiffer.
The couple share top billing in the Spanish Colonial encircled by a lush garden with a clowder of cats largely descended from Hemingway’s original six-toed pet, Snow White.
“Polydactyls were considered good luck charms,” said my tour guide, Mary Jane Pierce. “Hemingway was superstitious and accident prone. He figured he could use all the help he could get.”
On my visit, 66 cats — who have their own Instagram account — roamed the estate where docents regaled a steady stream of literary fans and cat lovers with tales of the author’s carousing, fishing and writing in the photograph-filled home.
Enough Hemingway, I thought, as I pedalled to the Key West Museum of Art & History. Yet here was an associated treasure worth the price of admission ($15.50): Fifty-nine pen-and-ink drawings by the wildlife artist Guy Harvey depicting Hemingway’s moving tale “The Old Man and the Sea” are mounted in the grand central staircase of the original 1891 Customs House in which the museum is situated.
Sunset circus and happy hours
For a few hours each evening before sunset, the energy vortex of Key West shifts to waterfront Mallory Square, a few blocks from the Customs House. In a tradition that stretches back to the 1960s, the west-facing public plaza attracts buskers and street acrobats keen to entertain the throngs searching for the elusive green flash that occasionally appears just as the sun disappears on the horizon.
New safety regulations adopted earlier this year after a performer and spectator were injured prohibit fire on the pier, so its flame-jugglers are gone. But the crowds remain, as do the guitarists, craft stalls and psychics.
It’s a compelling party, but I found better music at a pair of cover-charge-free music clubs. At Smokin’ Tuna Saloon, I listened to powerful country anthems from the guitarist Cliff Cody, a frequent performer, over a $7 tap beer.
As I was leaving with a glass half full, the bartender recommended I take it to go.
“The cops look the other way as long as it’s not a glass container and you’re not making trouble,” he advised.
That might be one way to stretch a drink, but awkward on a bike, so I ditched it and pedalled to Schooner Wharf Bar on the harbor. Nursing a $5 Key West Sunset Ale, I watched sailboats sway in the wind while listening to percussive rock covers from the guitarist Ken Fairbrother, who threw in “Grandma Got Run Over By a Reindeer,” because the October breeze, he said, “felt like Christmas.”
Happy hours and Cuban food
Key West is resolutely casual and there are lots of ways to dine cheaply. But for good food at value prices, timing is everything.
“Visitors do sunset then dinner, but locals will tell you to do it the other way around,” said Maria Wevers, the owner of the Grand Cafe with an inviting terrace on Duval Street that holds a daily happy hour from 4 to 7 p.m. with half-price drinks and appetizers.
That’s how — presunset — I came to try her grapefruit margarita ($9) and filling half-price dishes like smoked salmon toast ($9) and steamed clams ($8).
After the green flash eluded me once again, I pedalled on quiet streets to El Siboney Restaurant, a local Cuban favorite decorated with vintage travel posters of Cuba and portions so big I boxed half of my roast chicken with yellow rice and black beans ($14.95).
Just 90 miles from Cuba, Key West has welcomed migrants from the island since 1830s, which explains the abundance of Cuban food. For lunch the next day I rode to Sandy’s Café, a walk-up window in front of a laundromat famous for its strong coffee and pressed Cuban sandwiches ($9.75) layered with pork, ham and Swiss cheese. A few blocks away, I picnicked at the oceanside Key West Garden Club (free) lodged in a former Civil War fort.
That afternoon, before happy hour at Milagro Restaurant & Bar, a Latin-accented gem where the drinks ($14 for a hibiscus margarita) are two for one from 5 to 6:30 p.m., I toured the Key West First Legal Rum Distillery. Free tours start with a taste of a piña colada and end with complimentary rum samples.
A chef, Paul Menta, co-founded the distillery in 2012 to apply his palate to a category of booze he said is often doctored to mask impurities. His unique approach to distilling rum includes soaking his aging barrels in ocean saltwater before filling them and infusing flavors like Key lime in small batches.
“When you’re creative, in a lot of places you’re considered strange,” said Mr. Menta after the tour. “But in Key West, you’re among your people.”
The wild side
Though Key West is known for its wild lifestyle, I’ve always appreciated its wildlife. On previous trips, I’ve boated to nearby sandbars and shell-choked islets. I should have pushed past my budgetary restraint to book a snorkeling and dolphin-watching trip with Honest Eco, a reasonable deal at $99 for four hours on an electric boat.
Instead, at sunrise on my last day, I swam at Fort Zachary Taylor Historic State Park (pedestrian or bike admission $2.50), spying striped sergeant majors and pastel parrotfish.
On my way out, I stopped at the neighboring Florida Keys Eco-Discovery Center (free), focused on the surrounding Florida Keys National Marine Sanctuary, which protects the only barrier reef in North America. Exhibits examine its 2,000-plus shipwrecks, mangroves that act as nurseries for aquatic species, and carbon-sequestering sea grass beds.
“People don’t necessarily connect climate change to melting ice caps because they don’t see it, but here they can see how their behavior affects the reef and animals,” said Emily Kovacs, the center’s manager, as she pointed out coral in the water outside the museum that had bleached over the very hot summer.
Later, I visited the modest Key West Wildlife Center (free), a sanctuary devoted to rescued and rehabilitating wild birds. In large outdoor cages, brown pelicans were recovering from shredded throat pouches caused by discarded fish bones, raptors were treated for dehydration, and abandoned common gallinule hatchlings paddled in a tub.
When healed, most birds are released into the wild from the adjacent Sonny McCoy Indigenous Park, a hidden block of shady trees popular with birders and, on this afternoon, filled with the song of migrating palm warblers.
While I watched, Chris Castro, a volunteer wearing long leather gloves, carried a regal osprey from its rehab perch and launched him into the bright sky. The raptor’s wings beat deeply as he set a course over the sea where, waterlogged, he had been rescued just a few days earlier.
Like the ephemeral green flash at sunset, the stirring event was over in an instant, but proved once again that, despite its popularity, Key West rewards anyone paying attention, whatever their budget.
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