Coolest Block in Key West: Mallory Square

By Janet K. Keeler

It happens 365 times a year. Yet when the sun sets in Key West, people flock to the water’s edge as if it is their first time watching the sky go from blue to pink to orange to dark. At the decisive moment, smartphones are raised aloft to document the sight, proof positive to the folks back in Duluth, Denver and Des Moines that someone’s been to the Conch Republic.

Standing on the seawall, tiny Sunset Key is nearly swimming distance in front of them, Cuba is 90 miles to their backs and home is a million miles away even if it’s not. That’s the magical spell of Key West.

The coolest place to see the sunset in the American tropics is really a square. Mallory Square. Plunked on the north end of this 4.2-square-mile island heaven, the square and its colorful band of entertainers have brought the revelry for decades. About two hours before the sun drops beyond the Gulf of Mexico horizon, people start to gather to get a good spot and to people-watch. There is plenty to keep everyone occupied until the main show.

These days, there’s the guy swallowing fiery swords and another riding a mile-high unicycle while telling jokes. A psychic promises a glimpse into the future for a mere $25. A sure-handed fellow whacks the tops off coconuts to build the base for sculptural fresh fruit drinks. Lines form at the conch fritter stand.

A variety of musicians are stationed about. Congo players bring a pulsating beat to one corner of the square, attracting parents and their dancing kids. Wee ones who aren’t dancing chase pigeons or clamor for bags of fresh popcorn. A teenage guitar player makes a fashion statement, dressed head to toe in black gothic. So not a cheeseburger-in-paradise look but his indie-pop shtick fits the outfit as he pounds out an Arctic Monkeys song about looking for love in the middle of the night. “Come back after dark when I play the dirty stuff,” he tells a woman who drops some coin into his box.

Not far from Goth guy is a much older woman, also on the guitar. Her voice is wobbly but she matches the music to the scene. The Beatles I’ll Follow the Sun is her selection as the sun dips toward the horizon and the crowd gravitates en masse to the edge of Key West. A stronger singer of the same vintage wearing a felt bowler has put out his tip box near the conch fritter stand.

Key West is the last jewel in the strand of islands that stretches from Key Largo southwest, slicing through the Gulf of Mexico to the north and the Atlantic Ocean to the south. It might seem like it’s close to Miami but once you get through the bright lights and big city, there’s still got another 3.5 hours in the car on the Overseas Highway. Reality, and with it stress, fades in the rear-view mirror as each mile ticks past.

Key West has long marched to its own drummer, residents threatening every now and then to secede from the union. The inhabitants are fiercely independent and proud of the island’s history, which includes being a strategic location for military operations and home of the Harry S. Truman Little White House. The 33rd president discovered the charms of this tropical island long before cruise-ship merrymakers and bachelorette partiers roamed Duval Street with red Solo cups. He spent 175 days of his presidency in the home that can now be toured by the public.

The Hemingway House, where American writer Earnest Hemingway penned the short story “The Snows of Kilimanjaro” and the novel “To Have and Have Not,” is also open to the public. The annual Hemingway Days in July celebrates the author and his time in Key West. The signature event is the crowning of the Hemingway look-alike. Stocky men with close-cropped white beards cause visitors to do a double take.

A new Hemingway attraction is the Papa’s Pilar rum distillery near Mallory Square. Tours are available as are free tastes of the dark and light rums made there. Hemingway’s 38-foot fishing boat was named Pilar, the nickname of his second wife, Pauline.

Mallory Square is not without its own history. Today, big cruise ships that dock nearby bring throngs of happy travelers to the bars, shops and restaurants of Duval Street. (The party atmosphere along the main drag will remind many of New Orleans’ Bourbon Street.) But a couple hundred years ago, the ships that docked here were heavy with bounty from shipwrecks. Mallory Square has long been a hub of social and commercial activities.

Today there are nearby hotels to stay in, plenty of souvenirs shops to peruse and restaurants to fill the belly. Pepe’s Café opened in 1909 and is just a few blocks from the square. It’s a hot spot for breakfast and features a different quick bread (banana, mango, etc.) daily. Pepe’s is Key West at its funkiest. Two Friends Patio Restaurant is also a quick stroll away. It’s open until midnight, serving fresh local seafood.

On the square is El Meson de Pepe, which features Cuban cuisine. Sample picadillo or ropa vieja inside or outside and finish off the meal with guava bread pudding or key lime pie. Head to the patio of El Meson de Pepe just after sunset to listen to live music and do a little salsa. Dancers of all ages and abilities crowd the walkway. Nobody needs a partner, just the will.

No matter what’s in and around Mallory Square, be it the guy sketching caricatures or the woman shaving coconut ice, sunset is the main attraction. The daily sky show (and always hope there are clouds to make it more dramatic) is the siren song of Key West.