Add dates

Florida Keys Halloween activities

Our most recommended Florida Keys Halloween activities

The Dark Side of Key West Adults Only Walking Tour

1. The Dark Side of Key West Adults Only Walking Tour

Explore the spooky side of Key West on this ghost-themed adults-only walking tour that visits the city’s popular haunted spots. Become a history buff after learning about the historic events and figures that helped shape the unique culture of Key West. On this adult’s only option that focuses on Key West’s dark and salacious past, you'll discuss Count Von Cosel, Robert the Doll, and The Hemingway House. Hear all about the grisly murders, suicides, demonic deeds, and learn about the fascinating hauntings at each place. Find out the true stories behind these locations and more from a guide who is an expert on the dark, haunted history of Key West.

Key West: Bone Island Haunted Pub Crawl

2. Key West: Bone Island Haunted Pub Crawl

Join us for a ghostly guided walking tour into the heart of old town Key West's most haunted bars. On this haunted pub crawl you will experience why Key West is consistently ranked as one of the top five most-haunted cities in America. Crawl along as you delve into some of the more spirited pubs of Old Town. You'll discover Key West's history of cursed treasure, voodoo, murder, suicide, haunted mansions, unexplained deaths, and more. Your professional "ghost host" will introduce you to the darkest side of "Bone Island" with unbelievable stories of Key West's sinister past. You will receive our signature T-shirt to commemorate the event and cocktails are available for purchase along the way. The crawl ends in the heart of downtown Key West where you will be free to explore more.

Key West: Ghosts & Gravestones Guided Trolley Tour

3. Key West: Ghosts & Gravestones Guided Trolley Tour

Many find Key West a strange place during the day; but after the sun sets, the restless souls of the island’s frightful past begin to stir. On this 1-hour ghost tour, you will hear all-but-forgotten tales as you travel the dark and narrow streets of the Old Town. Pass 19th-century wooden houses that hold secret stories of former inhabitants; stories so tragic and chilling, you’ll soon see why Key West was named one of the top 10 most haunted cities in America. Learn the sinister story of creepy Count Karl Von Cosel and his dearly departed bride Elena Mesa. Hear tales of lynching, island superstitions, clandestine burials, murder and mayhem. Travel past many of the island's most haunted locations like the Marrero House, the Porter Mansion, and the Hanging Tree. Pass the former home of Robert Eugene Otto, where Robert the Doll suffered the abandonment of his lifelong companion, and his mischievous ways took a more sinister turn. Your Ghost Host will add a pinch of humor to Key West's dark side with tales of deathly love, tragic endings, scores to settle, wrongs to right and ghastly folk - some so strange it will be hard to believe they’re true…

Key West: Haunted Pub Crawl Walking Tour

4. Key West: Haunted Pub Crawl Walking Tour

Take a look at the Key West's dark past on a haunted pub crawl walking tour. From the island’s demonic dolls to one infamous case of necrophilia, not everything is glamorous in paradise. Hear all these stories with a drink in your hand as you make your way from bar to bar over an evening. First, head to Captain Tony’s Saloon — Key West’s most eccentric bar with bras on the ceiling and fake bodies beneath the floors. The peculiar tree in the middle of the bar has stained the ground it sits on, its victims still roaming the stools and bottles. Then make your way to Wine-O Bar & Lounge — a staple of Key West’s largest building, La Cocha Hotel. But with great praise comes great tragedy, as being the tallest building makes you a prime candidate for suicide. And with tragic suicides come tragic hauntings. Next, head over to The Roost, which serves some of the best cocktails in Key West. It's also neighbor to one of America’s most haunted city blocks. There, see Key West Theater, a place that houses many shows but used to house children’s screams, and the Artist House, which used to be the home to a cursed doll. Learn about how the Dean-Lopez Funeral Home was once home to a lover’s obsession gone wrong and the lengths he took to bring back the dead. Finally, stroll over to the old-fashioned Old Town Tavern & Beer Garden. You might find the spirit of Ernest Hemingway frequenting it, since his Key West home is right down the street. Hear stories about each haunted location, one drink at a time.

Key West: Ghosts of Key West Walking Tour

5. Key West: Ghosts of Key West Walking Tour

Explore the spooky side of Key West on this ghost-themed walking tour. See the city’s most popular haunted spots and hear fascinating stories about the ghosts of its past. Hear about Robert the Doll, the haunted doll with supernatural powers who sits in the city's East Martello Museum. Stop by the La Concha Hotel and learn about the ghostly legends contained within. See fascinating locations like the Hemingway House and the Artist House. Stroll the city's streets with a guide who is an expert on its dark, haunted history. Become a history buff after learning about the historic events and figures that helped shape the unique culture of Key West

Frequently asked questions about Florida Keys

What top attractions are a must-see in Florida Keys?

Other Sightseeing Options in Florida Keys

Want to discover all there is to do in Florida Keys? Click here for a full list.

What people are saying about Florida Keys

We have done numerous ghost tours throughout the country and world and this was by far one of the best. Erik made the tour extremely enjoyable and his vast knowledge of the history in Key West made it that much more memorable…

Nice evening out seeing the lights of the streets of Key West, and learning some little known facts about Key West.

This tour was good. Was able to see other things I wouldn’t expect to visit and learn many new things

The tour was a fun way to spend a couple of hours. Our guide was great—fun and funny.

Lots of fun, good interaction guides/customers, 9-year old granddaughter loved it