Key West's Dark Side: Unforgettable Haunted Trolley Tour
Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the narrow, dark streets of Old Town and hear stories from your guide about the island’s haunted history. This ghost and gravestone tour of Key West offers you an in-depth look into the strange and gloomy past of the Southernmost City.
Reviews
Reviews and Rating (Tripadvisor)
5 stars
4 stars
Reviews by Tripadvisor travelers
Katherine_M, 11/5/2025 9:34:31 PM
We really enjoyed howard and Arthur’s performance tonight! Lots of fun facts and interesting history. Just an overall great experience. We’ve done Savannah, Boston and now Key West! Very pleased
Rachael D, 11/5/2025 7:31:48 AM
Really good ghost tour in key west. Good way to learn about the history and darker history of key west. Definitely go when you first get here because then you can visit some of the spots you stop on the tour. I recommend a night tour
Tour643596, 11/4/2025 5:03:05 AM
Great tour. Driver was excellent, informative, humorous and courteous. The storyteller was superb. From her costume to her accent, she was engaging and delightful. A huge plus was we went on Halloween, and the streets were literally filled with ghosts, goblins and zombies!
Antonia_H, 10/31/2025 9:28:41 PM
This was a great tour. The tour guide,Violet, was very knowledgeable about the history while interjecting humor into the tour making it very enjoyable. Be sure to arrive early and be prepared to have a great time
Camille_M, 10/31/2025 10:57:28 AM
Enjoyed the history and very entertained Bobby the driver and the narrator were fantastic Would recommend
Sandi_R, 10/31/2025 9:19:33 AM
It was worth the money. The guide was well educated on the history of the town. Sites were great and worth seeing. A lot of fun.
Keith_G, 10/29/2025 8:08:09 PM
The most impactful part of the tour is the African burial site and the story behind it. It was deeply sorrowful that children were treated that way!
noeleenf89, 10/28/2025 9:52:30 PM
Some sadness to the stories but told with reverence. Mostly fun and enlightening. Big shout out to Violet and Howard for a truly memorable evening.
danmA3674CO, 10/28/2025 10:07:56 AM
The tour was fun, interesting and shared some really important facts about Key West history. Earl was a great host and set and maintained a great tone throughout the ride. The major drawback was that there were two riders who were distractingly talking during or over Earl and made the experience less enjoyable overall. During a stop in the ride, we talked to Earl about this and while initially they planned to just speak louder, he did call out the behavior as discreetly as possible later in the ride when the behavior wasn’t changing. While we wished those individuals could have shown more respect for the staff and attendees that night, it was still very enjoyable otherwise.
Jj_J, 10/14/2025 7:49:25 PM
the tour was so fun and they gave us so much information about the island! it was a really great experience
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
- Instant Confirmation
- This tour may not be suitable for children under 13 years of age. An adult must accompany children under 10 years of age. Due to the loud noises on our tour, children under the age of 4 are not allowed on board
- The tour runs most dark and stormy nights, so please dress appropriately. Please wear comfortable shoes aboard the Trolley of the Doomed
Departure point
Tour departs from 501 Front Street (Corner of Duval and Front St). Guests are required to check in 30 minutes prior to the scheduled departure time.Return details
Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the narrow, dark streets of Old Town and hear stories from your guide about the island’s haunted history. This ghost and gravestone tour of Key West offers you an in-depth look into the strange and gloomy past of the Southernmost City.Redemption
24 hours before travel date - 100% refund
Less than 24 hours before travel date - 0% refund