A must on every vacation I take is a city tour, usually on a double decker bus. In Key West, we chose to take the Conch Train Tour. It's a Jeep dressed up to look like a tank engine and it pulls the cars behind it. My sons are obsessed with Thomas the Train, so they loved it.
The Spanish called Key West "Cayo Hueso," which literally means "bone key." When the Spanish arrived, the area was littered with bones from Native American battles. The tour goes by the Little White House, where Truman used to stay, Hemingway's house, where you can still see the descendants of Hemingway's six-toed cats. Notable architecture is pointed out, specifically the Gingerbread Houses. These homes have an overlay of latticework on their porches. Some of the latticework is in the shape of gingerbread men, others show a symbol of the profession of the house's original owner.
Mallory Square is the area for boat tours. We took a glass-bottomed boat tour. This was beautiful. You get to see the third-largest coral reef in the world, lots of yellow-tailed snapper and the occasional barracuda. I recommend taking the tour that ends at sunset. The sunset in Key West is hard to describe, it's like the water swallows up the sun. The tour includes a champagne toast at sunset.
Whenever I am on vacation, I try to go on a ghost tour. I love ghost tours. Ghost tours give you a taste of the history of a city. The tour I took begins at the Concha Hotel, which is alleged to be haunted. A young man was trying to help his waiter friend clean up so they could get to a New Year's Eve party. He pressed a button to open the elevator doors, not realizing you had to push another button to actually call the elevator. He plunged down the shaft to his death. Apparently at certain times you can hear phantom dishes crashing. There was a tragic tale of a man who killed his wife and children. There's a theater built on the site, but the tenants never stay for long due to the supernatural activity. Our tour guide told us a story of a time when she had a particularly obnoxious child on her tour. The group was about a block away from the theater and the kid pointed at the building and said, "there's seven children over there and they're sad." She hadn't even started to tell the story yet. There's also typical ghost tour stories of lost love and voodoo. After the tour, go for a drink in the Concha Hotel's bar, it's lovely.
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