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Key West Trolley Day and Night Package

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ChildAge: 0-12 years old.

No Hidden Costs! Our low price includes all taxes and fees.

NOTICE: In response to the ever-changing COVID-19 situation, and for the well-being of our guests, employees and community, Old Town Trolley Tours of Key West has announced a temporary closure of the Old Town Trolley Tours and Ghosts & Gravestones Tour until further notice. Please check back for updates. -- Reservations required for Ghost & Gravestones tour.
FREE Admission to the Sails to Rails Museum is included.
Key West Trolley Day and Night Package Discount package including the 2 most popular tours in Key West. Spend the day sightseeing with Old Town Trolley. Then join Ghosts and Gravestones for a haunted tour at night.


  • Learn the history of Key West aboard the Old Town Trolley
  • Learn about Key West's wrecking industry
  • Tour at your own pace
  • Have an adventure on the Ghosts and Gravestones tour
  • FREE Admission to the Sails to Rails Museum
  • Complimentary admission to "Hemingway Rum Company, Papa's Pilar Distillery"
  • 100% Satisfaction Guarantee
Sit back while our expert tour guides turn back the pages of history to the days of Indians, pirates, wreckers and the Civil War. Old Town Trolley Tours of Key West is the best way to explore the southernmost city.

Learn about Key West's lucrative (ship) wrecking industry. Hear the stories of success and disaster of Henry Flagler's railroad... the railroad that went to sea. Listen to the legends of the fierce Calusa Indians that were said to leave the remains of their enemies on the beaches of Key West, thus creating Key West's first name, Cayo Hueso... Island of Bones.

Tour at your own pace! Old Town Trolley Tours allows you to get off at any of our convenient stops. When you're ready, just re-board and it's on with the tour.

Included FREE in this package is the new Sails to Rails Museum: A visit to Sails to Rails is one of the most comprehensive overviews of Florida Keys and Key West history a visitor can obtain. Guests to Sails to Rails will journey through the Age of Sail, a time when tail ships plied the treacherous waters of the Caribbean, Gulf of Mexico and Florida Keys from the 1500 to early 1900’s. These waters were once filled with treasure-laden Spanish Galleons, dreaded Pirates, merchant ships and more as the New World made its riches known to all who sailed her waters. A top attraction in Key West for adults and kids of all ages.

Ghosts & Gravestones of Key West offers guests an evening adventure exploring Key West's strange and macabre past. 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. Your tour will travel past many of the island's most haunted locations ~ the Marrero House, the Porter Mansion, and even the Hanging Tree! Of particular interest will be the former home of Robert Eugene Otto, aka the Artist's House. There, imprisoned in the attic by Dr. Otto's wife, Robert the Doll suffered the abandonment of his lifelong companion, and his mischievous ways took a more sinister turn.

The Trolley of the Doomed will then take you to explore the eerie East Martello Fort where guests will meet Robert the Doll ~ Key West's Most Cursed Resident!

Host guide you on an unforgettable adventure into the unknown.... if you dare.

Please note that the free portions of the ticket have no cash value and are not refundable and non-transferable. All promotions subject to change without notice.
Key West Trolley Day and Night Package Key West Trolley Day and Night Package
The best way to explore the southernmost city The best way to explore the southernmost city
Ghosts & Gravestones of Key West Ghosts & Gravestones of Key West
Sails to Rails Museum Sails to Rails Museum
An unforgettable adventure into the unknown.... if you dare. An unforgettable adventure into the unknown.... if you dare.
Boston Old Town Trolley with free Harbor Cruise


Key West Trolley Day and Night Package

Operating Times:

Old Town Trolley:Daily. 9:00 am to 4:30 pm 363 days a year. The last full tour is at 12:00pm Fri Oct 23rd. Closed Sat Oct 24th and opens at 10:00am Sun Oct 25th for Fantasy Fest.
Ghosts and Gravestones: Times vary according to date. Please see calendar.
Guests must check-in 30 minutes prior to tour time. Within 15 minutes of tour time, seat(s) are subject to cancellation. Tours do not run on July 4th, Fantasy Fest weekend in October, Christmas Eve and New Year's Eve.
Sails to Rails: Open daily from 9:00am - 5:00pm.
The Hemingway Rum Company, Papa's Pilar Distillery Tour: Open daily: Mon-Sat 10:00am -6:00pm; Sun 11:00am-6:00pm. Guided Tours are held at the top-of-the-hour between 11:00am-5:00pm: Monday- Friday and 12:00pm-5:00pm on Sunday.

Reservation Notes:

Ghost & Gravestones Tour - Reservations are required. Reservation based tickets and unused tickets are non-refundable. You may reschedule up to 24 hours in advance of tour time by calling 305-294-4678. Old Town Trolley Tour - Reservations are NOT needed or accepted. Tickets can be used on any operating day within 12 months of the purchase date.

# of Stops:

Old Town Trolley: 13 stops. eTicket holders may board at any of the following locations: (1) Mallory Square (1a) Truman Little White House (2) Historic Key West Seaport (3) Simonton Row - Simonton and Greene St (4) La Concha Crowne Plaza (5) Bahama Village Market (6) Fairfield Inn (7) HTA Roosevelt Depot (next to the Gates Hotel) (8) Best Western Key Ambassador (9) East Martello Civil War Fort (10) Casa Marina Resort (11) Southernmost Trolley Stop (12) Truman Ave. & Duval St. (13) Angela & Duval Streets


90 minutes

Booth Location:

Old Town Trolley Main Stop: Mallory Square, 303 Front Street
Ghosts & Gravestones: 501 Front Street (Corner of Duval and Front St)
Sails to Rails: 901 Caroline St. Key West, FL 33040
The Hemingway Rum Company, Papa's Pilar Distillery Tour is located at 201 Simonton Street (corner of Greene & Simonton).

Nearest Intersection:

Duval St. and Front St.


Parking is available at Mallory Square or The Margaritaville Parking garage.

Age Requirements:

Newborn-12 years old. The Ghosts & Gravestones Tour is rated PG-13. Tour may not be suitable for children under 13.


Old Town Trolley Tours depart from boarding locations approx. every 15-20 minutes. Patrons with etickets (voucher) or mobile ticket can board at any Old Town Trolley boarding location. Without a Ticket you must go to the ticket booth location with invoice order number. When purchasing eTickets for groups of 15 or more, please call Customer Service so that we may most effectively serve your needs.

Ghost & Gravestones Tours run most dark and stormy nights so dress appropriately. Part of tour is exploring the Civil War Fort and involves walking. Restrooms are not available during the tour. Accessible: We request 24-Hour advance notice. Please call 305-294-4678. OTT is not responsible for things left behind on the trolleys.

Key West Trolley Day and Night Package Booth Location
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