Key West Walking Tours

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Unlike most cities in Florida, compact Key West is very pedestrian-friendly, and the streets lined with historic mansions and cottages invite exploration on foot. It’s easy enough to navigate Key West’s grid on one’s own, but the history of the island is so rich, taking some time with a guide makes a wander much more rewarding. In fact, we went on three different walking tours on our recent visit to Key West. Each one proved thoroughly enjoyable and fascinating; I learned something new on all of them. Plus, the groups (or lack thereof) were small enough that I felt like I got to know an engaging local.

With no cruise ships docked in Key West due to COVID-19, these walking tours never had more than four participants. Depending on your interests, I recommend booking at least one of the options below, scheduling it toward the beginning of your visit to Key West. Any of them would make for an excellent introduction to life on the island.

Historic Homes and History of Key West


One of three walking tours offered by Hidden Key West, this approximately two-hour itinerary covered an impressive amount of architectural and historical ground. Groups are limited to 10 people, but we were joined by only one other couple. We met up with our guide, John, across from the Key West Museum of Art & History in the old Custom House. He pointed out how ill-suited the structure is to the local climate: D.C. bureaucrats required its design to include numerous fireplaces and edging along the roof line to prevent snow from sliding down onto pedestrians below. Across the square, John pointed out a much more sensible structure, a beautiful Bahamian colonial-style mansion built with no nails or screws, constructed with (now functionally extinct) Dade County pine. It was almost knocked down and replaced by a gas station. The story of the mansion’s last resident reminded me of “Grey Gardens,” the famous 1975 documentary film. John had numerous such stories, all of which he related in a conversational manner. Although he had seemingly encyclopedic knowledge of the island’s history and architecture, he never let the tour turn into a lecture. His great affection for Key West was obvious and infectious.

Key West Art Walk


The vivacious Maxwell leads the Key West Art Walk, and since there was a last-minute cancellation, we ended up having a private outing. His itinerary also started at the Key West Museum of Art & History, which displays works by a variety of top-quality local artists working in a range of media and styles. It felt very Key West to see, for example, a pretty watercolor depicting a southern French town hung next to a rooster painted on a toilet seat cover. Maxwell, a native artist who also lived for spells in Paris and Berlin, pointed out numerous telling details in works that we would have certainly overlooked. With our introduction to Key West art accomplished, we moved on to the Studios of Key West, an art deco building displaying rotating exhibitions of contemporary local artists, followed by a couple of notable commercial galleries with works that had something to say (many of Key West’s galleries sell pieces that are merely decorative). I was especially taken with the sculptures of Cindy Wynn and paintings by the Cuban collaborative group “Stainless.” Since there were so few of us, Maxwell ended the tour with a visit to the studios and living spaces he shares with a number of other artists. We met his neighbor and friend, Marlene Koenig, from whom I purchased a small encaustic depicting a decaying piano. We had great fun discussing the merits of various artworks with Maxwell on this tour, and I recommend the experience to anyone with an interest in the rich Key West art scene.

Old Town Literary Walking Tour


Although Key West is most famously associated with Ernest Hemingway, numerous other major literary figures lived (and live) on the island. To learn more about them, we booked this 90-minute Old Town Literary Walking Tour organized by Key West Literary Seminar, currently held on Fridays and Sundays. Only one other couple joined us and our guide, Scott, a well-read transplant from Los Angeles who knew many of the writers currently living in Key West personally. We departed from the historic peach-tinted Monroe County May Hill Russell Library, which sometimes hosts talks by authors such as Meg Cabot of “The Princess Diaries.” We passed by the bookshop, Books & Books, owned by Judy Blume, where, in nonpandemic times, she can often be found organizing the shelves, as well as the former home of Shel Silverstein and his neighboring “writer’s cottage” where he worked. Tennessee Williams, too, lived in Key West for decades and did a great deal to make it a literary center. Robert Frost spent time on the island as well. And Hemingway? Scott had a number of interesting anecdotes about him, involving alcohol and fights as often as not. At one point, I asked Scott what he thought of Hemingway’s writing. “I think… he’s important to read,” he replied, measuring his words carefully. As a writer and avid reader, I found this tour immensely enjoyable, but I have no doubt it would appeal to anyone even passingly curious about Key West’s history and the many important literary figures that populate it.

Read more about our editor’s trip to the Florida Keys

By Andrew Harper Editor Andrew Harper editors travel the world anonymously to give you the unvarnished truth about luxury hotels. Hotels have no idea who the editors are, so they are treated exactly as you might be.
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