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.