Take your seat on the Trolley of the Doomed and discover haunted Key West’s darkest side—the side you can only see at night.

Discover Key West’s darkest side—the side you can only see at night. We’ll travel along the dark, narrow streets of Old Town, where centuries old wooden buildings are said to be the home of raging occupants, souls who’ve never moved on. Learn the gruesome details of some of the island’s most tragic deaths, ghastly residents and more as your Ghost Host takes you on a tour of Key West you’ll not soon forget. The Travel Channel deemed Key West as one of America’s most haunted places; see for yourself during the Key West Halloween celebration.

With a history steeped in pirates, Indians, shipwrecks and buried treasure, it’s no wonder Key West has its share of haunted tales. Visitors to the southernmost city often spend some time seeking out the tiny island’s spookier spots hoping to have a paranormal encounter.

We’ve all experienced it: That eerie feeling that something or someone was watching us; that an inanimate object had, in actuality, come alive. In Key West, many have not only experienced that feeling, but have also witnessed it when viewing the famous toy – Robert The Doll.

A visit to this historic church and cemetery is indeed an experience – if not to simply enjoy its beauty, but also to explore the possibility that ghosts really do exist. Discover the haunted side of Key West on the Ghosts & Gravestones Tour.

The lost souls that were laid to rest, but never truly rested. Discover the city’s darker side when you visit these haunted cemeteries.

An island icon, Captain Tony’s Saloon has an intriguing past – one that includes murder, mystery, and even a bit of mayhem. Before becoming a popular watering hole, the building served a few different roles. It was an ice house, the city morgue, a wireless telegraph station, a cigar factory, a speakeasy and even a bordello. It was also the original home of the famous Sloppy Joe’s Bar.

When evening descends on the Conch Republic, a festive atmosphere permeates the air, and natives and visitors alike take to the streets for something fun to do at night. Because of its relatively small size, this island enclave is ideal to explore on two feet or two wheels. With many of its popular attractions within close proximity of one another, Key West is an easy and highly accessible town with plenty to offer when the sun goes down. Though Key West has a well-earned reputation as a party capital, with a robust nightlife packed with bars and a vibrant live music scene, this part of the world also has plenty to offer those looking for family-friendly activities to do at night. To get the most out of your visit, check out our list below of the best things to do at night in Key West, guaranteed to put a smile on everyone’s faces!

La Concha Hotel is located in the vibrant and bustling city of Key West. La Concha Hotel stands tall and proud as one of the oldest and most haunted attractions in the area. The hotel was built in 1926. This historic landmark has captivated visitors with its fascinating past and ghostly stories. It is situated on Duval Street, just around the corner from famous Key West landmarks such as Mallory Square, the Hemingway House, and the Key West Aquarium.

Nestled within the historical tapestry of Key West, the Curry Mansion Inn stands as an enigmatic testament to the past. Bearing the name of William Curry, a Bahamian immigrant whose fortune was forged amid the dangers of salvaging in pirate-infested Florida waters, the inn beckons with tales untold. Located at 511 Caroline St., Key West, the Curry Mansion Inn invites exploration into the heart of the Key West Historic District — an immersive neighborhood that weaves tales of a bygone era. As part of the entertainment district and in close proximity to the sun-drenched beaches, the inn unfolds an experience where the charm of history mingles with the mystique of the supernatural.

Duval Street in Key West is more than just a bustling hub of activity — it’s a destination where history, intrigue and the supernatural converge. Stretching from the Gulf of Mexico to the Atlantic Ocean, this iconic street offers visitors a taste of Key West’s unique charm, with lively bars, historic architecture and captivating local legends. However, beneath its cheerful exterior lies a shadowy past filled with ghostly encounters and mysterious stories that continue to captivate visitors. Dive into the haunted side of Duval Street.

Bone Island, as Key West is often called, carries a name that hints at its eerie and mysterious past. This unusual moniker comes from the island’s dark history, where tales of shipwrecks, buried bones, and restless spirits echo through time. For those interested in unique facts about Key West, this place offers no shortage of spine-chilling lore. Ancient legends, maritime tragedies, and mysterious artifacts all contribute to a past that feels both close and haunting. If you’re drawn to tales of the unexplained and want to explore some of the strange things about Key West, the story of Bone Island will capture your curiosity.

Key West, Florida, is a destination like no other, offering endless charm, rich history, and unique adventures for Key West first-time visitors. This tropical paradise, known for its lively culture and beautiful landscapes, is packed with activities that showcase the best of island life. If you’re visiting for the first time, here’s a guide to the unique things to do in Key West to help you make the most of your trip.

Key West is a destination full of surprises, offering visitors a blend of history, mystery and natural beauty. Beyond its famous sunsets and lively atmosphere, the island holds a wealth of unique stories and fascinating trivia that few people know. Dive into these unique facts about Key West, and discover what makes this island so special.