From Maritime Village to Micro State: A Guide to Key West’s Quirky History

Key West is famous as mainland America’s Caribbean resort town. Here, time slows down as the island vibes take over. But, as you’ll soon find out on this walking tour, there’s more to this island than umbrella drinks and warm breezes.

The tour starts in Mallory Square, the cultural center of Key West, and ends at Southernmost Point which, as the name implies, is as south as you can get in the continental US. Along the way, I’ll share stories of some of the island’s more famous residents, along with some lesser-known tales that have given Key West its unique place in American culture and history.

I’ll tell you about Key West’s incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships along the Great Florida Reef, to the hilarious creation of the ‘Conch Republic’. You’ll also find out how, soon after its creation, this micro-state declared war on the United States for a full minute.

On this two-hour tour, you’ll visit the island’s major landmarks and its lesser-known treasures too, stopping for refreshments along the way at many of its signature restaurants and bars, including Captain Tony’s Saloon and Sloppy Joe’s Bar.

On this Key West tour, you’ll have a chance to:

• Soak up the nightly Sunset Celebration, complete with street performers in Mallory Square
• Seize the moment like Mel Fisher while learning about his “Today’s the day” mantra, which fueled the 16-year search for the sunken Nuestra Señora de Atocha galleon ship
• Chill out with favorites like key lime pie or frozen key lime pops from Kermit’s Key Lime Shop
• Stroll down Caroline Street, one of the oldest streets in town
• Hear the origin story of one of America’s most iconic brands, Pan American Airways
• Pass by the Little White House, where President Harry Truman would escape when he tired of the ”Big, White Jail” back in Washington
• Stop by the Mile Marker Zero (the beginning of US Route 1) for a quick photo-op
• Take in the Key West Lighthouse, next door to the Hemingway Home and Museum where Ernest Hemingway and his second wife, Pauline, lived for nine years so that the author would be able to find his way home after a night of drinking

Join me for a fun and amusing walk through the island packed full of charm, quirky stories, and buried treasures.