Criminals & Crimes
Revived in Paradise
Key West, Fla 1980 –
Key West – known for swaying palm trees, famous authors like Hemingway and Tennessee Williams, laid back local lifestyle, and a place to escape…read more…
real life on the mainland – also has a dark side. Besides the drug smuggling that spurred a Florida Keys and Key West secession from the United States, other criminal activity like armed robbery – including a 1964 armored truck hijacking in broad daylight, multiple bank heists, and a holdup at a popular pool hall – has run rampant over the years. There’s a 1979 unsolved murder and the 1976 mysterious disappearance of a popular fire chief who may (or may not) have been a drug dealer. Illegal gambling during Prohibition ran through the streets and dark alleys along with the barrels of rum coming into the Key West harbor straight from Cuba, right past the Coast Guard, and into hidden spaces inside Key West’s popular speakeasy bars. iWITNESS True Crime brings the stories to life with captivating storytellers along the darkened streets of Old Town. It’s an experience like no other – with true crime happening all around us on our picturesque, laid-back tropical island. It’s not one of the popular ghost tours in Key West – we’re going back in time to experience the true stories of crime in Paradise. Be ready for the unexpected.
Real Crime. Real Locations. Unreal Stories.
🔍 90 minutes on the streets of Key West
🔍 Your guide? An expert witness
🔍 Your role? The next eyewitness to the island’s most notorious history
About true crime tours in Key West
Walk the postcard-perfect streets of Old Town and uncover Key West’s most unbelievable true stories. From smugglers to swindlers, scandals to schemes — these crimes really happened, right where you’ll stand.
Join your expert witness and a small group of fellow investigators, and experience the secrets that lurk in the darkside of Key West. It’s true crime – live, and up close.
Easy 90-minute stroll designed for everyone over the age of 17; walk about 6 blocks with multiple stops to talk crime and criminal activity at the scene of the crime.
Be The Next Eyewitness
Not your average ghost tour or history walk – iWITNESS True Crime puts you on the streets of Key West’s real crimes, outrageous scandals, and unforgettable stories & characters. Expect the unexpected…
Recent witness statement:
“So much fun!! I knew Key West had some crazy stories but wow! Plus the way they organized the tour and the surprises they had in store for us was fantastic….very creative and clever. When my family and friends come into town I’m definitely going to recommend this!” – Josh K. November, 2025 TripAdvisor Review