Above: The Richard Peacon House, built in 1885 and bought by Calvin Klein in 1980

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.

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Above: The Richard Peacon House, built in 1885 and bought by Calvin Klein in 1980

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