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Key West Day and Night Tour Package

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Old Town Trolley Tours: The island of Key West is full of fun and exciting things to do and see. From the Southernmost Point to the quaint streets of Old Town, our tour takes you to all the major areas and attractions. Ghosts & Gravestones Tour: Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir. You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town.

For over 30 years, Old Town Trolley Tours has provided sightseeing tours highlighting the best Key West attractions. Hop aboard one of our trolleys and you’ll experience Transportainment, a delightful combination of transportation and entertainment. Ghosts & Gravestones: Do you dare join the other brave souls aboard the Trolley of the Doomed to experience the strange, macabre and unusual side of Key West at night?

Your Key West Day and Night Tour Package Includes:

  • Old Town Trolley Tours:
  • 1 day of free unlimited re-boarding
  • Hop On & Off at 13 Old Town Trolley Stops
  • Open-air sightseeing perfect for taking pictures
  • More than 100 points of interest
  • Ghosts & Gravestones Night Tour:
  • Voted Top Ten Best Ghost Tour by USA Today Readers' Choice
  • Explore Some of Key West’s Most Haunted Sites…
  • End your voyage with a stop at the Key West Shipwreck Treasure Museum
  • 100% Satisfaction Guarantee
  • Tours do not have to be taken on the same day

Key West Old Town Trolley Tours

There’s no better way to see all of Key West than with Old Town Trolley Tours.

The island of Key West is full of fun and exciting things to do and see. From the Southernmost Point to the quaint streets of Old Town, our tour takes you to all the major areas and attractions. See Key West’s first tourist attraction, the Key West Aquarium, which was also the world’s first open air aquarium. Cross the street and you’ll find yourself back in the 1800s at the Key West Shipwreck Treasure Museum, learning about how Key West became one of the richest cities in the US. The Oldest House Museum is also nearby; it is one of the many beautifully restored homes that are open to the public in Key West.

Stop by the Ernest Hemingway House Museum where he is rumored to have written A Farewell to Arms — and don’t forget to look for the 6 or 7 toed cats! Marvel at the beautiful species of butterflies in the Key West Butterfly and Nature Conservatory, and wander next door to the Southernmost House Mansion and Museum, known for its 19th century architecture and tropical gardens. Cool off with a drink at the famous Sloppy Joe’s Bar or Jimmy Buffet’s Margaritaville in the Old Town area. But don’t leave Key West until you’ve watched the sunset from Mallory Square, a truly memorable experience!

Ghosts & Gravestones Night Tour

Your voyage begins with your Ghost Host, an unusual individual even by Key West standards, who will be your guide as you wander the streets of historic Old Town aboard the Trolley of the Doomed in search of the forgotten souls. Their tales of murder, disease and misfortune will take us out of the present and into the past in search of lost tombs, strange dolls, and the Lady in Blue.

You will pass by some of the most tragic and most sacred sites of the island such as the Grotto of our Lady of Lourdes, which protects the city from hurricanes, the African Slave Cemetery – site of the final resting place for 15 slaves who perished from their treacherous voyage – and even Captain Tony’s Saloon. You probably think it is only a bar… but is it? Even the majestic St. Paul’s Church, founded by Key West’s finest families, has secrets…

Your voyage on the Trolley of the Doomed ends with a stop at the Key West Shipwreck Treasure Museum deep into its cistern filled with tales of those who have haunted its dark past. As you journey upstairs you will discover “Daddy Long Legs” and the cursed silver bar from an ill-fated shipwreck in 1656. Then equipped with a ghost meter, you are then on your own to discover what else lurks inside.

We run on dark and stormy nights! Comfortable shoes are recommended so that you don’t become dead on your feet during the walking portion. Space is limited for this exclusive tour!

This tour may not be suitable for children under 13 years of age.

Safety is our First Priority

The safety and well-being of our guests and team members remain our highest priority.

  • We are providing hand sanitizer at key boarding locations throughout the city.
  • All of our vehicles undergo a deep cleaning procedure on a nightly basis.
  • We’ve enhanced our cleaning procedures at our sales depots and encourage guests to use cashless transactions.

Old Town Trolley Tours is taking enhanced safety and health measures for the benefit of our guests. Inherent risks to COVID-19 exist in any place where people are gathered. By using our services, you voluntarily assume all risks rising out of or resulting from exposure to COVID-19 or any other communicable illness.

Old Town Trolley Stops in Key West

Hop on and off at any of our 13 convenient stops.

  • 1
    Mallory Square
  • 1a
    Truman Little White House
  • 2
    Historic Waterfront/Mac’s Sea Garden
  • 3
    Simonton & Green Streets
  • 4
    Duval Street/Crowne Plaza La Concha
  • 5
    Bahama Village
  • 6
    Fairfield Inn
  • 7
    Roosevelt Station at Gates Hotel
  • 8
    Hampton Inn
  • 9
    East Martello Fort/ Robert The Doll
  • 10
    Casa Marina Resort & Beach House
  • 11
    Southernmost Point Trolley Stop
  • 12
    Truval Village
  • 13
    Angela Street Depot

Booth Locations

Stop 1 - Mallory Square Inside Mallory Square (between Shell Warehouse and Sponge Market)

Stop 3 - Simonton Row Corner of Simonton and Greene Streets

Stop 12 - Truval Village Corner of Truman Avenue and Duval Street

Stop 13 - Angela Street Corner of Angela and Duval Streets


Old Town Trolley Tours

First tour starts at 10am.
Last tour departs from Mallory Square at 4:30pm.

Daily 364 days a year.
(We are closed the last Saturday in October for Fantasy Fest)
Tours depart at least every 30 minutes.

Length of tour: 1 hour and 30 minutes if you ride the tour all the way around without getting off and on.

All schedules are subject to change. Please call (855) 623-8289 for the most current information.

Ghosts & Gravestones Tour

Nightly: 7:00pm, 8:00pm, 8:30pm, 9:30pm and 10:00pm.

Ghost tours are subject to availability and extremely popular during Halloween, so be sure to make a reservation for the haunted tour now!

Please call 305-29-GHOST (305-294-4678) for more information.

Length of tour: 1 hour

This tour may not be suitable for children under 13 years of age. Due to the loud noises on our tour, children under the age of 6 are not allowed onboard. Availability in late October is extremely limited.


*Ghosts & Gravestones: Reservations required. Reservation based tickets are non-refundable. You may reschedule up to 24 hours in advance of tour time. Tours do not have to be taken on the same day.

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