Key West for book lovers
Literary greatness is woven into the fabric of Key West’s cultural scene, as much as the island’s storied bars, scofflaw smugglers, and wayward artists
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From Ernest Hemingway to Truman Capote and Tennessee Williams, authors have long been drawn to the furthest tip of Florida, with its pastel-hued, palm-fringed tropical beauty and fierce embrace of all things edgy and eccentric. “Writers are part of the background in Key West,” says Arlo Haskell, executive director of Key West Literary Seminar, an annual celebration of its bookish culture that has been taking place for more than 40 years. The 45-year-old is himself a long-running thread in that colorful backdrop, a literary “Key Wester” born and raised.
Haskell’s parents moved to the Keys in the ’70s and his mother ran the Key West Literary Seminar for several years—he has led the program since 2015, attracting writers of the caliber of Margaret Atwood, John Banville, and Robert Caro to the island city each January.
He is also a poet, author of The Jews of Key West: Smugglers, Cigar Makers, and Revolutionaries, and served two years as Key West’s honorary poet laureate, one of literature’s least demanding posts. “Blessedly, there were no responsibilities whatsoever,” he laughs.
“Key West is very small—less than 5 square miles in all,” says Haskell. “Roughly half of this land area is what we call Old Town—a densely habited mix of residential and commercial properties, and home to the Key West Historic District. The other half, New Town, is mainly residential and, frankly, not nearly as interesting.” But despite its small size and population of just 26,000, Key West’s literary legacy packs a punch.
“Ernest Hemingway came right after The Sun Also Rises was published. Tennessee Williams stayed for about 40 years until his death. Hemingway kept [his boat] Pilar in what is today called the Historic Seaport,” Haskell notes. “Williams would go swimming every morning at Higgs Beach. Truman Capote used to stay at the Pier House, whose proprietor, the legendary David Wolkowsky, outfitted a small trailer for him to stay in whenever he wanted.”
Haskell’s encyclopedic knowledge of Key West’s writing scene stretches across dozens of locations around town, and digs much deeper than the literary giants most visitors remember from high-school English class.
“[Pulitzer Prize-winning poet] Elizabeth Bishop was here in the ’30s and ’40s. Her letters are the richest description of Key West from almost 100 years ago, but the Old Town neighborhood where she was living is much the same today—eminently walkable and bikeable, and there are lots of hidden lanes and alleys with significant literary history,” he says.
Visitors interested in seeing some of the former homes and favorite haunts of Key West writers can join Haskell’s Old Town Literary Walking Tour. “Our tour includes the Writers’ Compound on Windsor Lane, former home of Ralph Ellison, John Hersey, and Richard Wilbur; Casa Antigua on Simonton Street, where Hemingway first stayed; Shel Silverstein’s former home on William Street; James Merrill’s old house on Elizabeth Street; and Tennessee Williams’ first apartment near the corner of Caroline and Duval.”
Ed Needham
Writer
Ed Needham is an award-winning magazine editor and journalist. Previously a long-term resident of Barcelona and New York, he currently lives in London, where he is the publisher and editor of the literary magazine, Strong Words.
Where to stay
Overview
“The historic Old Town is where you want to stay,” Haskell says. “The Marquesa is first rate—a lot of our writers stay there during the Seminar and you are right in the heart of walkable downtown Key West, he says. “But if you want a blast-from-the-past glimpse of what the Florida Keys used to be like, stay at the Sugarloaf Lodge on Sugarloaf Key (17 miles from Key West).”
Haskell also recommends that, wherever you stay, be sure to get out on the water. “That’s our wilderness and the real beauty of this place.”
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What to do
Overview
While the Hemingway Home & Museum is one of Key West’s most popular attractions, Haskell encourages visitors to take a deeper dive. “The Tennessee Williams Museum is worth seeing, and we are in the midst of restoring Elizabeth Bishop’s home,” he says.
Haskell has a few reading recommendations for optimizing your trip, too: “Read Wallace Stevens’ The Idea of Order at Key West—go out late at night along the harbor and you are right in his poem.” To potentially rub elbows with a contemporary great, Haskell recommends dropping into Books & Books. “Judy Blume (author of Are You There, God? It’s Me Margaret) fell in love with Key West in the ’90s and now runs this wonderful bookstore.”
Above all, Haskell recommends visitors plan their trips for January to attend the Key West Literary Seminar. “It’s the main event for readers and writers in Key West, and the thing that keeps our life of letters alive!”
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Where to eat and drink
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Many restaurants and bars around town also have storied pasts. “There is a great little hole-in-the-wall called the Chart Room, which has history from the ’60s and ’70s when Thomas McGuane and Jim Harrison were around.” When McGuane’s classic Key West novel 92 in the Shade was adapted for a movie, the final cast party was at the Afterdeck bar at Louie’s Backyard. “Definitely go here for a drink when the moon is up,” Haskell says.
“The Green Parrot has been Key West’s best bar for 100 years or so; and for a really good drink and an upscale vibe, try the tiny bar at Café Marquesa or Point 5, upstairs from Nine One Five restaurant, which is also very good.”
Fantastic dining options abound, too, and fresh seafood is almost always on the menu. “For excellent food with great service and attention to detail, try Blackfin Bistro and sit outside in the garden courtyard,” Haskell says. “And all three of the restaurants run by wife-and-husband Kristen Onderdonk and Tommy Quartararo are great: fresh seafood at Little Pearl and Thirsty Mermaid, or classic Italian at Antonia’s.
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