Duval Street may get all the glory, but this one-mile stretch serves up the essential quirky cultural finds that define Key West.

Key West isn’t like anywhere else in Florida. Actually, Key West isn’t like anywhere else period. And it especially shows on Whitehead Street. Where other town’s main cultural streets are crowded with shops and restaurants, this one-mile stretch reaching from the Southernmost Point of the Continental United States to the Mel Fisher Maritime Museum is mostly lined with old-school bungalows in either white or bright, tropical shades of pink, blue, and green. And rather than cars on the street, you’ll find Key West’s peculiar mix of scooters, golf carts, and tour vehicles like trollies and trains parked under monolithic bushes of flowering bougainvillea. Mixed among the charming homes, you’ll find some restaurants and boutiques, but more importantly, you’ll find some of the Key’s most important cultural destinations. When it comes to things to do in Key West, exploring Whitehead Street should be number one.

Carpe Diem Ice Cream

Carpe Diem Ice Cream [101 Whitehead Street]

Seize the day at this tropical-colored shop, offering over 20 different handmade ice cream and sorbet flavors. Think cake batter, orange pineapple, and black raspberry fudge served in pristine rolls that are then decked out with whipped cream, fresh fruit, Pirouette cookies, and other fun toppings. They are almost too cute to eat. Along with ice cream, the shop offers smoothies, cookies, and key lime pie, of course.

Mile Marker Zero [501 Whitehead Street]

Route 1 runs all the way from Fort Kent, Maine, along the Canadian border down 2,369 miles to Key West. The end (or start, depending on who you ask) is right on Whitehead Street complete with a 0-mile marker sign which collects almost as many visitors as the southernmost buoy. After snapping your picks, pop into End of the Road, right across Fleming Street,  for souvenirs for both the Route 1 terminus and Key West as a whole.


Street Smart: Key West’s Whitehead Street

Green Parrot Bar [601 Whitehead Street]

This bar has stood at the corner of Whitehead and Southard since the end of the second World War when it was a haven for sailors stationed in the area. Since then, the bar has been a hot spot for hippies, bikers, and all kinds of local characters who call the Key home. Inside you’ll find wall cluttered with ephemera of the Key’s past under a parachute tacked to the ceiling creating the sense of walking under a big top. Between the history, the “everyone is welcome” atmosphere, and the calendar of live music, the Green Parrot has been voted Best Bar in Key West and the United States on multiple occasions.


Street Smart: Key West’s Whitehead Street

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Ernest Hemingway Home and Museum [907 Whitehead Street]

Full of the six-toed descendants of Hemingway’s cat Snow White, the Key West home of this literary giant is open to the public. Spread across the two floors of the house, the residence has been kept much as it was when “Papa” lived there from 1931 to ’39. Tour the gardens and house or visit the bookshop to pick up the full works of Hemingway and his contemporaries and other Key West novelties, or head over to the Moondog Café right next door for a Cuban coffee.

Key West Lighthouse [938 Whitehead Street]

Climb up the 88 steps to the top of the spiral staircase of one of the oldest lighthouses in the country (the 15th oldest of more than 800) and take in the sweeping and uninterrupted view of the key and the waters beyond. Alongside the lighthouse and built into the home of the old lighthouse keeper, the Keepers Quarters Museum features displays on the history of both this light and others around the Keys and southern Florida.


Street Smart: Key West’s Whitehead Street

Rockhouse Gallery [330 Julia Street]

Located on the corner of Whitehead and Julie, this art gallery looks like a squat old church, but step through the front doors to find an ultra-modern gallery spread across two floors. The walls are lined with vibrant coastal art by award-winning local artists like watercolor artist Joan Becker and deep-sea photographer Tony Ludovico. Along with wall art, the gallery houses Pacific Green furniture, a sustainable and beautiful line of chairs created by hand from sustainably sourced palmwood and recycled materials.


Where to Stay  The Laureate Key West