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Trolley and Sails to Rails Package

Certificate of Excellence
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. Guests to the Sails to Rails Museum will journey through the Age of Sail, a time when tall ships plied the treacherous waters of the Caribbean, Gulf of Mexico and Florida Keys from the 1500s to early 1900s.
TYPE RETAIL PRICE SAVE UP TO
Adults $52.70 $43.13 $9.57
Children (4-12) $21.13 $16.87 $4.26
Children under 4 FREE FREE

Attraction tickets do not have to be used on the same day.

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. Sails to Rails Museum: A visit here is one of the most comprehensive overviews of the Florida Keys and Key West history you can obtain. It is a top attraction in Key West for adults and kids of all ages.

Your Trolley and Sails to Rails Package Includes:

  • Hop On & Off at 13 Old Town Trolley Stops
  • Exciting, Fully Narrated Tour of Key West
  • 100% Satisfaction Guarantee
  • Sails to Rails Museum:
  • Discover the Age of Sail in the Caribbean, Gulf of Mexico and the Florida Keys
  • View a diorama of Fort Jefferson National Park
  • Lift a genuine silver bar from the Spanish galleon Nuestra Señora de Atocha
  • Hands on, immersive activities for children and adults
  • Attraction tickets do not have to be used on the same day
  • Complimentary admission to 'Hemingway Rum Company, Papa's Pilar Distillery' included with your ticket

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.

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!

Included With Your Trolley Ticket: Hemingway Rum Company, Papa’s Pilar Distillery

Discover how rum makers craft their unique spirit, uncover the untold stories of Ernest Hemingway and experience an adventure Papa would be proud of!

Sails to Rails Museum

Sail power was used the day the treasure fleets returned from Mexico and South America, initially to rid the Caribbean of piracy, and in the industries that made Key West the richest city per capita in the United States: sponging, turtling, fishing, wrecking, and cigar making.

The end of the Age of Sail came with the beginning of steam power in the 1820s and during the Civil War years of the 1860s, when the vicissitudes of industry gave way to the speed and reliability of steam. Despite its rapid decline, sail remained part of the industrial fabric of Key West until its last ship was built in 1939: The Western Union, the cable tender serving its namesake company.

There was a time in America when railroads opened up the frontiers of an emerging nation. Railroads meant connection to commerce, wealth, and politics of a young country. In a sense, the United States of America was built on the foundation of its railroads, and Florida was certainly no exception.

In 1900, the life expectancy of males in the United States of America was a mere 47 years. Henry Flagler was 70-years-old and one of the wealthiest men in the world from his partnership with John D. Rockefeller in the founding of the world’s largest company, Standard Oil of New Jersey. For the health of his wife, Henry Flagler first came to Florida in 1885 and became entranced with the dream of seeing it become the country’s Riviera. His aspirations for luxury hotels along the East Coast of Florida developed it into the state it is today.

Realizing that the Panama Canal was going to be completed in 1913, Henry Flagler in 1897, first conceived of establishing a rail head in the southernmost deep-water port of the state: Key West. Thought to be impossible and even labeled “Flagler’s Folly,” the Key West extension was begun in 1905 and was, indeed, an engineering marvel.

Old Town Trolley Stops in Key West

  • 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
    Best Western Key Ambassador
  • 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

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Old Town Trolley Tours

9am – 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.

Fantasy Fest Schedule:
October 26: 9:00am – 12pm
October 27: Closed
October 28: 10:00am – 4:30pm

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.

First Tour of the Day:

Stop #1: Mallory Square: 9:00am

Stop #1a: Harry S. Truman Little White House: 9:02am

Stop #2: Key West Seaport: 9:05am

Stop #3: Simonton Row at Greene Street: 9:10am

Stop #4: Crowne Plaza La Concha: 9:15am

Stop #5: Bahama Village: 9:20am

Stop #6: Fairfield Inn: 9:25am

Stop #7: Roosevelt Station at Gates Hotel: 9:35am

Stop #8: Best Western Key Ambassador: 9:40am

Stop #9: East Martello Fort: 9:45am

Stop #10: Casa Marina Resort: 9:50am

Stop #11: Southernmost Trolley Stop: 9:55am

Stop #12: Truval Village: 10:00am

Stop #13: Angela Street depot on Duval Street: 10:05am

Last Full Tour of the Day:
Please note that guests taking this tour will not be able to use the on/off feature.

Stop #1: Mallory Square: 4:30pm
(Last reboarding time: 5:30 pm)

Stop #1a: Harry S. Truman Little White House: 4:32pm
(Last reboarding time: 5:32 pm)

Stop #2: Key West Seaport: 4:05pm
(Last reboarding time: 5:05 pm)

Stop #3: Simonton Row at Greene Street: 4:10pm
(Last reboarding time: 5:10pm)

Stop #4: Crowne Plaza La Concha: 4:15pm
(Last reboarding time: 5:15pm)

Stop #5: Bahama Village: 4:20pm
(Last reboarding time: 5:20pm)

Stop #6: Fairfield Inn: 4:30 pm
(Last reboarding time: 5:00pm)

Stop #7: Roosevelt Depot: 4:35pm
(Last reboarding time: 5:05 pm)

Stop #8: Best Western Key Ambassador: 4:40pm
(Last reboarding time: 5:10pm)

Stop #9: East Martello Fort: 4:45pm
(Last reboarding time: 5:13pm)

Stop #10: Casa Marina Resort: 4:50pm
(Last reboarding time: 5:20pm)

Stop #11: Southernmost Trolley Stop: 4:55pm
(Last reboarding time: 5:25pm)

Stop #12: Truval Village: 5:00pm
(Last reboarding time: 5:30pm)

Stop #13: Angela Street depot on Duval Street: 5:05pm
(Last reboarding time: 5:35pm)

Sails to Rails Museum

Open daily from 9:00am-5:00pm

Reservation Notes:
Reservations are NOT needed or accepted. Tickets can be used on any operating day within 12 months of the purchase date.

Duration: 45 minutes

Booth Location:
901 Caroline St.
Key West, FL 33040

Nearest Intersection:
Margaret St. & Caroline St.

Parking:
Paid parking nearby

Age Requirements:
Child age: 4-12 years. Under 4 are free.

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