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America's Strangest City Tours

Twin City Tacky Tours, St. Paul

Courtesy of Wasbasha Street Caves

Your heart’s pumping. Celeb hangouts and towering palm trees fly by. You try, in vain, to keep your oversized sunglasses on your face as you run along Rodeo Drive as if being chased by Nikon-wielding photogs. It’s all in an afternoon’s fun with Los Angeles’s “Running from the Paparazzi” tour. Where else but Tinsel Town can you pretend to be a star trying desperately to ditch overzealous photographers?

Guided city tours are ubiquitous, of course—New York City alone has more than 300 of them, according to the tourism office. And while it’s impossible to say how many of these are weird, offbeat, or downright strange, many have been borne of imagination and ingenuity. In fact, there’s no shortage of experiences for curious travelers looking for alternatives to the omnipresent sightseeing bus.

“You can see more of the real city this way,” says Drew Raphael, owner of Dead Apple Tours, who was inspired to create his 1968 hearse tour of New York City after seeing folks stopping by the SoHo building where actor Heath Ledger died. He compares his tour to “rolling performance art or rolling theater,” where those interested in Gotham’s morbid hot spots cruise Downtown in “Desdemona,” Raphael’s formerly casket-toting vehicle.

Often started and led by passionate experts on niche subjects—or those who see an opportunity in creating fun and unusual travel memories—offbeat tours can take you to spots you’ll never read about in guidebooks or find while walking through the city on your own.

“You feel as if you’re in a house that hasn’t been opened in years,” says Katharina Woodworth of one of the city’s strangest, most popular, and longest-running guided tours—Underground Tour. Accessed via a flight of stairs in Doc Maynard’s Public House, a restored 19th century saloon, the supposedly haunted tunnels are the remains of the original city that was destroyed by the Great Seattle Fire of 1889. (The current city streets were built on top.) “It’s like walking through catacombs into a secret world that takes you back a century to the real Seattle.”

As for souvenirs from these crazy tours, you are practically guaranteed interesting tales to tell family and friends back home.

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