Book Now
Street Smart: Key West’s Whitehead Street
Back

Street Smart: Key West’s Whitehead Street

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, a one-mile stretch reaching from the Southernmost Point of the Continental United States to the Mel Fisher Maritime Museum that 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 [101 Whitehead Street]

Carpe Diem Ice Cream

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.

Ernest Hemingway Home and Museum [907 Whitehead Street]

Street Smart: Key West’s Whitehead Street

© Shutterstock.com

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.

Where to Stay Sunset Key CottagesThe Laureate Key West Opal Key Resort & Marina | The Capitana Key West

You may also like
A couple strolls to the edge of the dock at Lake Placid Lodge at sunset.

Romantic Getaways That Will Sweep You off Your Feet

If you’re looking for romantic getaways in the United States, we got five worthy – and diversly different – picks in Opal destinations, just for the two of you. How do you like to rev up the romance? Do you…

Read more
The Running of the Bulls with during the Hemingway Days event.

The Top 2024 Key West Festivals You Won’t Want to Miss

A look at the conch-blowing contests, Hemingway lookalikes, and mind-blowing masquerades to frame a 2024 Key West vacation around. (Feature image) © Andy Newman | Florida Keys News Bureau For such a small island – sizing in at just 4.2…

Read more
A ice sculptor carves out an piece for the annual Glacier Ice Bar.

Opal’s Coolest Attraction: Inside The Annual Glacier Ice Bars

Simply a swan sculpture it is not. The Glacier Ice Bars that descend upon The Sagamore Resort and Samoset Resort each January are Instagram eye-candy extravaganzas entirely made out of ice. If you’re visiting The Sagamore Resort or Samoset Resort…

Read more
The view of Frenchman Bay from Bar Harbor

A Coveted Coastal New England Road Trip

The beauty of a multi-day, 220-mile road trip up the craggy coast from Portsmouth, New Hampshire to Bar Harbor, Maine isn’t just the plethora of enticing pit stops along the route – from high culture to scenic coves. It’s also…

Read more