by Shayne Benowitz

A quaint conch cottage in Old Town.

A quaint conch cottage in Old Town.

Did you come to Key West with even a hint of curiosity about its famous literary past? Well, if so, I’m going to let you in on a lovely way to see the island through the eyes of some of its former famous inhabitants. All you need is a handy map from the Fury Surf Shack and a rented bicycle (two feet and a pair of flip-flops work, too!)

April is National Poetry Month and in Key West, we are also celebrating with the Robert Frost Poetry Festival. You might be surprised at how many notable poets made Key West their home for years at a time or for the occasional retreat. Follow this itinerary for a bike ride down quiet lanes lined with lush palm trees and colorful bougainvillea to see the homes where these famous poets lived.

From Fury’s office at the Margaritaville Marina, you’ll see Whitehead Street intersect with Caroline Street. Here you’ll find the Heritage House & Museum. Robert Frost retreated to a writing cottage on these grounds during the winters of 1945-1960. Thornton Wilder and Wallace Stevens also made the Heritage House their home.

Continue up Whitehead Street until you reach number 529 where Elizabeth Bishop first lived in the 1930s just down the street from Papa Hemingway. She hopped all over the island and we’ll get to a few more of her houses later.

Take a left on Angela Street and pedal two blocks until you cross Elizabeth Street. Angela turns into Windsor Lane. Windsor lines Key West’s historic cemetery and you’ll also find a compound where poets Richard Wilbur, John Ciardi, Ralph Ellison, and John Hersey all spent time working on their verse.

Windsor Lane will turn into Passover Lane as you cross William Street. Take note that much-loved poet Shel Silverstein took up residence on William for a time. Continue to ride along the cemetery until you hit Frances Street at the other end. At number 611, you’ll find Elizabeth Bishop’s final Key West cottage.

Why not round out the tour on White Street? Today it is home to the artist compound The Studios of Key West. In 1938, our gal Elizabeth Bishop lived at number 6. It’s a beautiful bike ride through the heart of Old Town Key West, so you might as well get all poetic about it!

Shayne Benowitz is a Fury crewmember and freelance writer working on her debut novel. For more travel stories and a daily dose of what’s cool around the globe visit her Wanderlust Website at

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Last Updated 07/31/2023