My Key West favorites, from Hemingway's six-toed cats and the Southernmost Point to Cuban coffee, conch fritters, and key lime pie. These are the spots I send every friend heading to the end of the road.
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The Hemingway Home is my first stop in Key West, where I tour his writing studio and say hi to the six-toed cats.
The Hemingway Home and Museum
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I always wait in line for a photo at the Southernmost Point buoy, just 90 miles from Cuba.
Southernmost Point of the Continental U.S.A.
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I climb the 88 steps of the Key West Lighthouse for the best rooftop view over Old Town.
Key West Lighthouse
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Mallory Square's nightly Sunset Celebration is a must, with street performers, conch fritters, and the sun dropping into the Gulf.
Mallory Square Market
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Fort Zach is my favorite beach on the island, with clear water for snorkeling and shady picnic spots next to a Civil War fort.
Fort Zachary Taylor Historic State Park Beach
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The Little White House tour shows where Truman spent his winter working vacations, and the guides are full of great stories.
Truman Little White House
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The Butterfly Conservatory is a calm escape from Duval, with hundreds of butterflies and two flamingos named Rhett and Scarlett.
The Key West Butterfly and Nature Conservatory
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Audubon House is a peaceful 1840s home and garden where I browse the original Audubon bird prints.
Audubon House & Tropical Gardens
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The Shipwreck Museum tells the story of Key West's wreckers, and I climb the lookout tower for a view over Mallory Square.
Key West Shipwreck Museum
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The Mel Fisher Maritime Museum has real treasure from the Atocha shipwreck, including gold bars you can lift.
Mel Fisher Maritime Museum
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Fort East Martello is a quirky brick fort museum, and it is home to Robert the Doll, the island's famously haunted toy.
Fort East Martello Museum
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I wander the Key West Cemetery for its above-ground tombs and funny headstones like ‘I told you I was sick.’
Key West Cemetery
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The Key West Botanical Garden is the only frost-free tropical forest garden in the continental US, and I love spotting birds at its ponds.
Key West Tropical Forest & Botanical Garden
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Higgs Beach is my laid-back local beach, and I walk out to the end of the White Street Pier at sunrise.
Clarence S.Higgs Memorial Beach
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Smathers Beach is the island's longest stretch of sand, perfect for a lazy afternoon with a paddleboard.
Smathers Beach
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I walk Duval Street end to end, from the Gulf to the Atlantic, popping into bars, galleries, and shops along the way.
Duval St
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The Historic Seaport boardwalk is where I watch the boats come in and pick my sunset sail.
Key West Historic Seaport
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I take the Yankee Freedom ferry out to Dry Tortugas National Park for snorkeling around Fort Jefferson, the best day trip from Key West.
Yankee Freedom Dry Tortugas Ferry
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Sloppy Joe's is the classic Duval Street bar Hemingway loved, and there is always live music going.
Sloppy Joe's Bar
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Captain Tony's is the original Sloppy Joe's location, full of bras on the ceiling and dollar bills on the walls.
Capt Tony’s Saloon
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The Green Parrot is my favorite locals' bar on the island, with killer live blues and funk most nights.
Green Parrot Bar
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Schooner Wharf is my go-to open-air bar on the harbor, with live music and cheap drinks under the palm thatch.
Schooner Wharf Bar
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Blue Heaven is my favorite brunch in Bahama Village, with roosters wandering the courtyard and a towering key lime pie.
Blue Heaven
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Pepe's has been open since 1909, and I come for the breakfast and one of their award-winning mojitos.
Pepe's Cafe
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B.O.'s Fish Wagon is a ramshackle shack where I get the grouper sandwich and conch fritters.
B.O.'s Fish Wagon
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El Siboney is my pick for Cuban food, and I order the roast pork with plantains and black beans.
El Siboney Restaurant (Downtown)
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Louie's Backyard is where I go for a special dinner on the water, or just a sunset drink at the Afterdeck Bar.
Louie's Backyard
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Garbo's Grill is an Airstream food trailer turning out my favorite mango-dragon shrimp tacos.
Garbo's Grill @ Hanks!
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Kermit's is my key lime stop, and I grab a frozen slice of key lime pie dipped in chocolate on a stick.
Kermit's Key Lime Pie Shop - Elizabeth Street
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Cuban Coffee Queen is where I start my mornings with a cafe con leche and a pressed Cuban mix.
Cuban Coffee Queen Waterfront
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Eaton Street Seafood Market is my spot for a lobster roll and fresh-caught fish with no fuss.
Eaton Street Seafood Market
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Hogfish Bar & Grill on Stock Island is a real working-waterfront hangout, and I always order the hogfish sandwich.
Hogfish Bar & Grill
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Sloppy Joe's is the classic Duval Street bar Hemingway loved, and there is always live music going.
