Discover Amazing Key West

Immerse yourself in the legendary history and undeniable charm of Key West as you embark on an extraordinary journey with Historic Tours of America. Get ready to discover the true essence of Key West through engaging and authentic experiences that seamlessly blend entertainment, education, and exploration.

Old Town Trolley logo
Conch Tour Train logo
Key West Aquarium logo
El Meson de Pepe logo
Harry S. Truman Little White House logo
sails to rails logo
Mallory Square logo
yankee freedom logo
Key West Shipwreck logo
Ghosts & Gravestones logo
Key West sunset at Mallory Square

Step into a world where the past comes alive...

…where iconic landmarks and hidden gems share fascinating stories. Join us on this unforgettable adventure and create cherished memories that will stay with you for a lifetime.

Board our iconic orange and green trolleys and be transported back in time. Decades ago, our founders united to preserve Key West’s historic sites and create an exciting sightseeing adventure. Today, Old Town Trolley Tours of Key West offers the ideal way to explore the city’s intriguing points of interest, accompanied by humorous and informative narratives that bring the stories to life.

Hop aboard one of our trolleys and you’ll experience Transportainment®, a delightful combination of transportation and entertainment.

Key West Old Town Trolley and Custom House

Join us as we journey through the colorful streets, stopping at iconic sights that have shaped Key West’s vibrant culture and rich history. With the freedom to hop on and off at convenient stops, you can immerse yourself in the local ambiance and explore at your own pace. Our passionate trolley conductors are storytellers, offering fascinating insights into notable events and the captivating individuals who have left their mark on Key West. From resident legends to artists, poets, and musicians, Old Town Trolley Tours brings their stories to light.

Preserving Key West's landmarks is not just a commitment to the past, it’s an investment in the future.

Truman Little White House

These cherished sites connect us to the roots of this remarkable city and serve as living memorials to its rich heritage

Historic Tours of America takes pride in showcasing Key West’s historical significance and contributing to its cultural vitality. Through our immersive experiences, we aim to foster a deeper appreciation for Key West’s unique charm, its pivotal role in history, and its profound impact on American culture.

Conch Tour Train at depot

Beyond our commitment to preserving history, we are dedicated to supporting the local community. By partnering with local organizations, participating in educational programs, and actively engaging in community events, Historic Tours of America strives to make a positive impact and ensure the longevity of Key West’s cultural legacy. Together, we create a lasting legacy that celebrates the spirit of Key West and preserves its treasures for future generations.

Join us as we celebrate the magic of Key West and its extraordinary attractions.

Key West Aquarium fish

Let us be your guide to the city’s timeless beauty, vibrant culture, and fascinating landmarks. Explore the captivating history, bask in the breathtaking scenery, and create cherished memories. Historic Tours of America is honored to showcase Key West and share its profound contributions to America’s rich tapestry. Together, let us preserve and treasure the heritage of this remarkable city.

couple at Key West conch fritter stand


Choose Your Tickets

Whether you’re just breezing through or enjoying an extended stay, we’ve got several options to choose from to help you maximize your time in Key West and still see the best first!

1-Day Trolley

  • 1 day of free unlimited re-boarding
  • Open-air sightseeing perfect for taking pictures
  • More than 100 points of interest
  • FREE coupons worth up to $50 in discounts
  • FREE admission to the Sails to Rails Museum
  • Exclusive stops and Key West attraction discounts
  • 100% satisfaction guarantee

Ghosts & Gravestones

Key West Ghosts & Gravestones trolley and ghost hosts
  • Voted Top Ten Best Ghost Tour by USA Today Readers' Choice
  • Explore Some of Key West’s Most Haunted Sites…
  • Pass by Some of the Most Tragic and Most Sacred Sites of the Island
  • Your voyage includes a stop at the Key West Shipwreck Treasure Museum

1-Day Conch Tour Train

Conch Tour Train and Sloppy Joes
  • 1-day tour of the Conch Republic
  • One full loop through Old Town Key West
  • Includes three stops
  • FREE coupons worth up to $50 in discounts
  • FREE admission to the Sails to Rails Museum
  • Highlights marvelous sights, stories and entertainment
  • Open-air sightseeing perfect for taking pictures

2-Day Trolley

Key West trolley and beach
  • 2 consecutive days of free unlimited re-boarding
  • Open-air sightseeing perfect for taking pictures
  • More than 100 points of interest
  • FREE coupons worth up to $50 in discounts
  • FREE admission to the Sails to Rails Museum
  • Exclusive stops and Key West attraction discounts
  • 100% satisfaction guarantee

2-Day Conch Tour Train

Conch Tour Train and Southernmost House
  • 2-consecutive day tour of the Conch Republic
  • One full loop through Old Town Key West
  • Includes three stops
  • FREE coupons worth up to $50 in discounts
  • FREE admission to the Sails to Rails Museum
  • Highlights marvelous sights, stories and entertainment
  • Open-air sightseeing perfect for taking pictures

Key West Aquarium

guide feeding shark while guests look on at the Key West Aquarium
  • Daily shark and turtle feedings
  • Touch Tank offers guests hands on experience
  • Featuring a wide variety of fish including grouper, moray eels, barracuda, tropical fish, tarpon, parrotfish and more

Truman Little White House

Harry S. Truman Little White House
  • See the home Harry S. Truman came to relax and rest
  • History tellers share fascinating stories of the most important man of his time
  • Visit where Eisenhower recuperated from his heart attack in 1956
  • Thomas Edison resided here during World War I

Key West Shipwreck Treasure Museum

Key West Shipwreck Treasure Museum guests and host
  • Discover the world of Shipwrecking
  • Hear the story of the Isaac Allerton
  • Climb a 65' Captain's Observatory
  • Lift a silver bar salvaged from a Spanish galleon
  • Enjoy a video presentation about the shipwrecking industry

Sails to Rails Museum

Sails to Rails Museum exhibit
  • Discover the Age of Sail in the Caribbean, Gulf of Mexico and the Florida Keys
  • Lift a genuine silver bar
  • Enjoy video presentations on the Overseas Railroad
  • Hands on, immersive activities


Step Back in Time and Explore Key West Culture


Sample Tastes, Sights, and Sounds

Groups, Charters & Weddings

Plan an unforgettable experience for your group event with Historic Tours of America.

Groups & Charters

  • Enjoy discounted rates
  • Custom design your rental
  • Private tour guide provided for charters
  • Combine a rental with attractions


  • Bring your guests to your event on time
  • Ride in classic Key West style
  • Personalize your trolley or train ride
  • Be treated to a red-carpet experience!

Hometown Pass

Locals receive Free Admission!

Included* with Your Key West Hometown Pass:

  • Old Town Trolley Tours
  • Conch Tour Train
  • Key West Aquarium
  • Truman Little White House
  • Sails to Rails Museum
  • Shipwreck Treasure Museum
  • Ghosts & Gravestones
Key West trolley driving by Casa Marina

Our Free Hometown Pass is the best way to entertain visiting friends and family!

Monroe County Residents can take advantage of some of our tours and attractions for FREE when accompanied by an adult full-fare paid guest.* It’s Simple, Fast & Best of all… Free!

Key West Shipwreck Treasure Museum at Mallory Square
Key West trolley driving by Casa Marina

Get all the information you need


The Old Town Trolley Tour is a 90-minute, fully narrated tour of Key West, but with the 13 stops, free re-boarding, and an all-day pass, the tour can last as long as you want!

All of our tours are in English.

Parking on a 2 mile by 4 mile island can be difficult. Our tour route and stops are at convenient locations all around the island, within walking distance of most major hotels and attractions.

Food and drinks are welcome. However alcoholic beverages are not allowed under any circumstance for the safety and comfort of all of our guests.

Service animals are the only animals that are allowed on board the trolleys. A service animal means a dog, regardless of breed or type, that is individually trained to do work or perform tasks for the benefit of a qualified individual with a disability, including a physical, sensory, psychiatric, intellectual, or other mental disability. Animal species other than dogs, emotional support animals, comfort animals, companionship animals, and service animals in training are not service animals.

If the guest is ambulatory, collapsible wheelchairs can be accommodated at any time. We will fold them and stow them during the tour. Guests may board and disembark at any stop. Indeed, a number of our fleet are equipped with motorized lifts that can accommodate scooters and/or wheelchairs. We are happy to provide this service, but ask for a few small accommodations to allow us to do so with the utmost safety and minimal impact on other guests utilizing our service. If a guest is non-ambulatory or has a non-collapsible chair/scooter, we do have several trolleys and trains equipped with hydraulic lifts. For the safety of the guest, the lift can only be deployed at certain stops.

We request that you give us as much notice as possible as to your arrival date and the time you’d like to take the tour (24 hours preferred). This will assure that a properly equipped vehicle will be made available for your use. Please arrive at your pre arranged stop no less than 15 minutes prior to your departure time so that we can accomplish the loading process smoothly and safely. This means that you will need to secure your own transportation to one of these locations and that you cannot utilize the ON/OFF privileges on the tour. Because of the high volume of our stops, including significant traffic density and uneven pavement, use of the lift outside of these locations would be inadvisable.

We are closed the last Saturday in October for Fantasy Fest.

The tour focuses on Old Town Key West and its history.

Yes, we can accommodate strollers but they must be collapsible and will be stored up front with the conductor. Strollers in the aisle ways would constitute a safety hazard.

Guests can choose to attend any of our public presentations where we delve a little deeper into one of the exciting exhibits here at the aquarium. All presentations are free with admission and are a good way to learn a little bit more about some of the amazing animals we have here in the Florida Keys.

That is entirely up to our guests if they would like to follow a tour. We recommend browsing the exhibits on your own and making time for a tour if your schedule allows. Please remember that our tickets are not transferable.

The average time our guests spend at once is 45 minutes to an hour.

Fishing is allowed from the shores of the Dry Tortugas as long as you have a current state of Florida salt water license which must be purchased before boarding the Yankee Freedom.

There are no public restrooms available at the park. Visitors will be required to use the facilities provided onboard the Yankee Freedom. Composting toilets will be available for visitors to use within the campground and after 2:30 PM. Composting toilets are specially designed toilets that do not require water or chemicals and they can accommodate a small number of users. These toilets are extremely fragile, and throwing trash or other materials into composting toilets is strictly prohibited.

No, there are no cell phone towers in the Dry Tortugas.

The designated snorkel area is right off shore, and depths generally range from very shallow to 15 feet.

It can help you gain a new perspective and you get to explore the city in the dark and very different way.

Yes. Ghosts & Gravestones has a limited number of seats per tour and frequently sells out.

YES! The tour runs on dark and stormy nights. The only time tours will be cancelled due to weather is if conditions prove to be too dangerous to proceed. In this event all reserved parties will be notified.

This tour is rated PG-13 and is not intended for young children. It is not a haunted house; but it is a historical tour turned completely on its head. We use haunted house style moments, historical facts, and creative storytelling to thrill, entertain, and scare our guests.