It’s Five O’clock Somewhere and even though it may only be 11 a.m. in Key West, the crowds at Margaritaville and Sloppy Joes have A Lot of Drink About. Florida’s furthest-south island, that attracted Hemingway and Harry Truman and whole generations of sons of sons of sailors is still partying heartily.
We’re docked here on Explora 1, the newest luxury ship in cruising, to spend the day among throngs of other tourists who have arrived by plane, car, motorcycle, and speedboat. The whole town depends on tourists and there was no hint that anyone was anything but enthusiastic that we’re joining the party. Come in, take a load off and check out the merch and kick back an over-priced Bama Breeze.
Oh yeah, that vote they had to ban cruise ships? Forget about it! It made the headlines in 2020 when residents of Key West passed a referendum to reduce the number of cruises visiting the island daily. Its supporters warned city officials that ever-larger cruise ships were coming to Key West and spending the day drinking and buying souvenirs and then sailing away.
But even though the island thinks of itself as an independent Conch Republic, it’s still part of Florida. The state legislature soon voided the voter referendums and further prohibited any municipality from doing anything that restricts maritime commerce in the state.
Turns out, there’s not much the city could do to control cruise ships anyway. The convenient dock downtown is privately owned and it’s got a right to book cruise ships without government control. And while the city owns the second pier near Mallory Square, the rents from cruise ships help pay for upkeep of the waterfront and create jobs.
While Explora Journeys‘ 900-guest Explora 1 was the only ship in port today, most every cruise line that sails from Florida has some itineraries that include Key West. Many days, two ships tie up in the same morning bringing thousands of passengers each. And of course, they sail away around five o’clock, when the real cocktail time kicks in.
So, the cruise ban is history and it’s back to business as usual. Let’s join the crowds taking a walk on the wild side.
There’s really no need to book a tour here because the Mallory Square pier is right at the foot of Duval Street, the main tourist haunt. Even though this was a Saturday, it wasn’t busy at all on the sidewalks on streets that are the realm of tour trains, rental scooters and Harleys. For a little more action, you can rent a jet ski or take a sightseeing boat from the edge of the cruise dock.
It was a week after Halloween and a lot of the left-over skeletons and glitter were on sale for half price, alongside the usual stock of T-shirts with logos and slogans that would make a sailor blush.
The shopping includes skimpy beach wear and lingerie that some visitors seem to think is just right to wear on the street at high noon. Shops feature jewelry made from “genuine” doubloons from Spanish shipwrecks. cigars, watercolor paintings and souvenir shot glasses along with things that are straight out of sci-fi movies. Walgreens and CVS drug stores are here, neatly camouflaged in former theaters and landmarks. New in the shop mix are dispensaries selling cannabis for medicinal purposes.
Every block is awash with places to eat and drink. Key West has avoided the big brand fast food outlets and dining is still a sit-down affair. There are a few name brands like Hard Rock Café and of course Margaritaville, but the best bets for unique cuisine are the mom and pops that serve local lobster and conch and Cuban specialties. The food comes at tourist prices, but at least it’s fresh-made and presented with flair.
At the moment, you can’t avoid Jimmy Buffett, with memorials everywhere to the Margarita-worshiping troubadour who first arrived in Key West in 1971 and made a legend with tunes about its laid-back lifestyle. The stores are filled with tributes and pricey mementos of the lifestyle hero who passed away at the age of 76—on Long Island, New York of all places. His music echoes through the speakers of bars.
If you want to get away from it all and get a feel for what Key West might have felt like in the quieter old days, walk a few blocks north to Upper Duval – or, as locals call it, uptown. The clapboard home district is being reborn as an elegant and highly walkable area of unique boutiques and attractions that counter the island’s castaway reputation. New shops offer merchandise difficult to find elsewhere and side streets are lined with rows of freshly renovated gingerbread cottages and grand Victorian homes that date to the late 1800s, when Cuban immigrants set up hand-rolled cigar factories in the area.
Getting back on our ship from our wander around the city proved a bit of a challenge. Even though Explora Journeys‘ first ship was sailing from Miami, and Key West—as we’ve already established is still part of America– was our first stop, there was an immigration check to go through to get back on the ship. We were supposed to have brought our passports or drivers licences ashore and it took the intervention of the security officer on the ship to get us back on board.
It wasn’t five o’clock yet, but it was time to settle in to a bar on board Explora 1 to raise a toast to the fact we can still visit this unique outpost of Florida’s history from a cruise ship.
Story by Wallace Immen, Executive Editor, The Cruisington Times
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