Haunted Houses & Ghost Tours in Key West, FL

The history

Key West's haunted reputation starts with its first name. Ghosts & Gravestones' haunted guide records that, long before it was known as Key West, Spanish explorers dubbed the island Cayo Hueso — literally "Bone Island" — after discovering human remains scattered along its shores.

The island's built haunted ground is mostly 19th-century. Fort East Martello, Sloan's Key West Ghost Tours records, has stood watch over Key West since the Civil War era, and is today a museum operated in connection with the Key West Art & Historical Society. The Hemingway House, Ghost City Tours' haunted-locations writing records, was built by notable Key West salvager Asa Tift in 1851; Ernest Hemingway lived there during the 1920s and 1930s, and the home is now a historic house museum and National Historic Landmark. Ghosts & Gravestones' guide adds an earlier visitor who did not stay: John James Audubon visited Key West in 1832 to find tropical bird specimens for Birds of America, stayed less than two weeks, and — the guide says — never stayed overnight on the island, choosing a boat in the harbour because he feared yellow fever.

The wrecking trade that made men like Tift rich left its own artefacts. Ghosts & Gravestones' Key West FAQ describes a cursed silver bar recovered from a 1656 shipwreck, now at the Key West Shipwreck Treasure Museum, and a dark underground cistern at the same museum. Captain Tony's Saloon, its haunted guide records, worked through a long list of earlier lives before it was a bar — ice house, city morgue, wireless telegraph station, cigar factory, speakeasy and bordello — and was the original home of Sloppy Joe's Bar.

The legend

This section is folklore — reported by tour companies and their guests, and never asserted as fact here.

The island's most famous resident is a doll. Sloan's own Robert the Doll page says Robert began as the childhood companion of Key West artist Robert Eugene "Gene" Otto, that stories of strange behaviour surrounded the doll for decades and became part of Key West folklore, and that visitors on display have reported malfunctioning cameras and electronic devices; the museum, the company says, continues to receive apology letters from people who believe they offended him and then suffered bad luck. Ghosts & Gravestones' FAQ tells the earlier, more folkloric version: legend says a disgruntled servant cursed a handmade doll given to young Gene Otto in the early 1900s at the Artist House, after which it reportedly moved on its own and giggled, and Gene's family reported seeing it perched in windows. Two tellings, one documented donation — in 1994 Myrtle Reuter donated Robert to the Key West Art & Historical Society, per Sloan's — and the rest is legend, labelled as such.

The Hemingway House lore is Ghost City Tours' telling: the house is rumoured to be haunted by Hemingway and his second wife, Pauline; people sensitive to such things claim to hear a typewriter, and a couple is said to have seen Hemingway wave from the veranda in 1961, realising only after news of his death that they believed they had seen a ghost. Ghosts & Gravestones adds the Shipwreck Museum's "Daddy Long Legs," the ghost of a legendary wrecker said to haunt the museum's upper floors and to be linked to that 1656 silver bar, and reports — its word — of strange sightings and a heavy presence near the artifacts. None of these reports is a documented event, and this page presents them at exactly that strength.

Haunted today

Hountix lists 6 places in Key West, FL. Seasonal attractions keep their own open dates, so check each business's own site before you go.

• Bone Island Haunted Pub Crawl & Ghost Tour — ghost tour, 424 Greene St, Key West, FL 33040
• Ghosts & Gravestones Key West — ghost tour, 501 Front St, Key West, FL 33040
• Key West Ghost and Mysteries Tour — ghost tour, 429 Caroline St, Key West, FL 33040
• Original Key West Pub Crawl and Bone Island Haunted Pub crawl — ghost tour, 424 Greene St, Key West, FL 33040
• Sloan's Key West Ghost Tours - Robert the Doll Experience — ghost tour, 3501 S Roosevelt Blvd, Key West, FL 33040
• The Original Key West Ghost Hunt — ghost tour, 301 Whitehead St, Key West, FL 33040

Attraction stories

Sloan's Key West Ghost Tours — Robert the Doll Experience

Sloan's Key West Ghost Tours calls its headline experience "Robert the Doll After Dark," and its own page is unusually clear about what it is not: "A real historic fort. A real museum. No actors. No haunted-house effects." The experience runs after Fort East Martello closes. The Essential tier, the page lists, is 60 minutes — a 30-minute ghost tour of the fort and a 30-minute seated encounter with Robert. The VIP tier is two hours and adds a 60-minute independent paranormal investigation, with equipment provided — the page lists spirit boxes, thermal cameras, dowsing rods, REM pods and other tools — and access to the fort's citadel, which the page says was once said to have been used as a makeshift hospital. Prices on the page as fetched were from $39 direct for Essential and from $79 direct for VIP; confirm current pricing and dates on the business's own site. Guests must be 10 or older.

The doll's documented spine is short and the company itself supplies it. Robert began, Sloan's says, as the childhood companion of Robert Eugene "Gene" Otto; after Gene's death he remained with the next owner of the Otto home; in 1994 Myrtle Reuter donated him to the Key West Art & Historical Society, and he has lived at Fort East Martello ever since. The fort, the page adds, has stood since the Civil War era and is associated — the company's phrasing — with more than 42 documented spirits.

Everything beyond that spine is reported experience, and the page frames it that way. The company also states plainly that paranormal activity is never guaranteed and nothing is staged. That candour is the story: an after-hours museum encounter whose one verifiable fact — a doll donated in 1994 to a Civil War-era fort — carries a century of attributed folklore on its back.

*Website: https://www.ghostkeywest.com/ghost-hunt-robert-the-doll-experience*

Ghosts & Gravestones Key West

Ghosts & Gravestones is Historic Tours of America's Key West ghost operation, and its vehicle is the pitch: guests ride the "Trolley of the Doomed" through Old Town with a costumed Ghost Host, on a tour its FAQ lists at approximately 60 minutes, beginning and ending at the Conch Tour Train Depot at 501 Front Street, with check-in at least 15 minutes before departure. The company says the tour was voted in the Top Ten Best Ghost Tour by USA Today Readers' Choice, runs rain or shine — "on dark and stormy nights" — and is rated PG-13 in its FAQ material, not suitable for young children.

The tour's distinctive stop is inside the Key West Shipwreck Treasure Museum. Its own tour page says the voyage includes a stop at the museum, deep into its cistern, and upstairs to "Daddy Long Legs" and the cursed silver bar from an ill-fated shipwreck in 1656. Its FAQ expands both, with attribution intact: the cistern is a dark underground water reservoir said to be haunted by the spirits of those who worked the wrecks off the coast, and Daddy Long Legs is the ghost of a legendary wrecker said to haunt the upper floors, linked to that silver bar, with guests and staff reported to have felt a heavy presence near the artifacts and lookout tower.

The route's other repertoire is named on its own pages: the Lady in Blue, lost tombs, Captain Tony's Saloon, St. Paul's Church and the Grotto of Our Lady of Lourdes, which its tour page says protects the city from hurricanes — presented here as the tour's own claim about local belief. Its FAQ is also clear on a limit visitors should know: the trolley passes near the East Martello Museum and tells Robert the Doll's legend, but it does not go inside to see him; for that, the company directs visitors to the fort itself — which is Sloan's experience, above.

Practical facts: start and finish at 501 Front Street, arrive early for check-in, and confirm current times, prices and accessibility arrangements — the FAQ asks guests needing accommodations to call at least 24 hours in advance — on the company's own site.

*Website: https://www.ghostsandgravestones.com/key-west*

Sources

• Sloan's Key West Ghost Tours — "Robert the Doll After Dark" — https://www.ghostkeywest.com/ghost-hunt-robert-the-doll-experience (fetched 2026-10-22, story-material/fl-key-west)
• Ghost City Tours — Key West Ghost Tours — https://ghostcitytours.com/key-west/ (fetched 2026-10-22, story-material/fl-key-west)
• Ghost City Tours — "The Haunted Hemingway House" — https://ghostcitytours.com/key-west/haunted-key-west/haunted-hemingway-house/
• Ghosts & Gravestones — Key West Ghost Tours, About, Haunted Guide, FAQs and Tickets pages — https://www.ghostsandgravestones.com/key-west (fetched 2026-10-22, story-material/fl-key-west)
• Ghosts & Gravestones — Key West ghost-tour tickets page — https://www.ghostsandgravestones.com/key-west/ghost-tour-tickets