Each year, thousands of visitors come to Key West to see the attractions, enjoy the magnificent weather and get their own taste of paradise, after all, there’s no place quite like it on earth. Old Town Trolley Tours of Key West offers a comfortable seat, a humorous and interesting narrative and a way to see the best of the city at your own pace.

The orange and green trolleys transport guests around the city of Key West, showing off the city’s most intriguing points of interest and sharing the fascinating stories that helped shape one of the country’s most visited destinations. From the colorful cast of transplanted Conchs, like Harry Truman, James Audubon and Ernest Hemingway, to the resident legends, artists, poets, and musicians that make Key West so alluring, Old Town Trolley Tours gives every visitor a look at the people and places that the city is so famous for.

On board the Old Town Trolley, guests of all ages are given a 90-minute tour through Key West with numerous stops at the most popular sights. You may hop on and off at our convenient stops throughout the day. From Mallory Square and Duval Street to Henry Flagler’s historic Railroad Museum - and everything in between, the trolley tour is a showcase of all the best of Key West.

Throughout the tour, knowledgeable trolley conductors offer an amusing, historic account of many of the most well-known Key West events and sights; it’s our own unique brand of Transportainment! So next time you’re in town, climb aboard and get set to be thoroughly entertained!

Here are just a few reasons why Old Town Trolley is the best sightseeing tour in town:

From 1828 to 1850 Key West was the richest city per capita in the United States.

• 100% Money Back Guarantee* (No Questions Asked)

• Ride Second Consecutive Day Free

• Kids 12 and Under Ride Free

• Military and Senior Discounts

• Top rated on Trip Advisor

• Full color map and discount coupons for attractions, restaurants and shopping with every ticket

• Hop on and off at your leisure

• Key West's most comprehensive tour fully narrated by our expert tour conductors

• On and off FREE reboarding at 12 stops

• Colorful anecdotes and well-research historical facts

• Exclusive stops and attraction discounts

• More than 100 Points of Interest

With your train ticket, you will receive our full color free map along with our coupon sheet; valued at over $50, the coupons include discounts for attractions, restaurants and shopping.

If you’re born in Key West you are a conch. If you’re born elsewhere but live here 7 years you become a fresh water conch.

• 100% MONEY BACK GUARANTEE*

• Kids 12 and Under Ride Free

• Military and Senior Discounts

• Ranked Top 20 on Trip Advisor

• Full color map and discount coupons for attractions, restaurants and shopping with every ticket

• NEW STOP! Truval Village: Steps away from the Ernest Hemingway Home and Museum, the Key West Lighthouse, the Southernmost Point and Key West Butterfly and Nature Conservatory

With all its natural beauty, Key West has a multitude of exciting activities—the Key West Aquarium tops the list with magnificent displays of the numerous marine animals that make the waters around the island their home.

Hold a live starfish or pet a shark! At the Key West Aquarium you’ll get closer than you’ve ever been (without getting wet) to some of the world’s most intriguing marine species. Opened in 1934, the Key West Aquarium was the very first attraction in the city; it was also the largest aquarium of its kind at the time.

Today, it’s twice the size and showcases many of the sea animals that live in the waters surrounding the Florida Keys. See moray eels, stingrays, barracuda, parrotfish, tarpon, sharks, sea turtles and an array of tropical fish. Learn about their habitats and habits from the Key West Aquarium’s knowledgeable guides.

Have a hands-on experience like never before as you see, feel and pick-up the amazing animals that live in the Touch Tank. They are all harmless, gentle creatures just waiting to get a closer look at you! Listen carefully as Aquarium staff reveal facts and information about these mysterious species.

Be sure to be on hand as hungry sharks and sea turtles devour their breakfast, lunch or late afternoon snack; feedings occur daily at 11am, 1pm and 4:30pm. The Atlantic Shores exhibit offers visitors a chance to learn about a mangrove environment. And the 50,000-gallon tank is home to many colorful and lively tropical and game fish.

In 1934 Key West was the poorest city in Florida. President Roosevelt, under the WPA program, had the Key West Aquarium built which is still in use today.

It was a time when pirates and indians roamed the shores looking for fortune and battling for territory. It was a place when human bones lay scattered in the sand - a vivid symbol of the passion and determination of those who came first. Cayo Hueso or Bone Key, was Key West’s first name, deemed so by the first Spanish settlers who discovered the remains on the beach when they arrived. Cayo Hueso, soon became Key West, when English-speaking residents at that time erroneously translated the name.

Throughout its vibrant and colorful past, Key West has undergone many changes and been home to people from all walks of life. But perhaps none with such a rich influence as that of the Cuban people. In the 1860’s, Cuban Cigar makers flocked to the island to work and sell their sought-after product. Their presence on the island made such an impact that Key West was soon referred to as “Cigar City USA”.

Today, Key West’s rich Cuban heritage is still apparent throughout the island. Casa Cayo Hueso y Habana Historeum offers a unique journey to that era for all who visit. Located in the heart of historic Mallory Square, the Historeum is housed inside an antiquated brick warehouse that dates back to 1879.

Sample the tastes, sights, sounds and culture of Cuba as you stroll through this marvelous collection of shops, displays and the well-known Pepe’s Casa Cayo Restaurant. Witness the skill and mastery of the craftsmen who meticulously hand-roll authentic Cuban cigars—see for yourself what makes a Cuban Cigar so extraordinary. View beautiful and intriguing art and memorabilia and learn more interesting facts about the original Cayo Hueso. Delight in the delicacies of Cuba and savor the true flavors that became a lasting part of Key West. A visit to the Casa Cayo Hueso y Habana Historeum is fun and entertaining for people of all ages.

Visited by Presidents, dignitaries, royalty, Prime Ministers and an array of prestigious people, the Harry S. Truman Little White House in Key West holds a special place in the history of the United States. It was here that President Truman came in search of a place to rest and relax. When our 33rd President arrived he discovered much more than a peaceful island hideaway, he found a place he’d like to call home.

Built in 1890 as quarters for the Naval Base Commander and Paymaster, the Little White House took its place in history early on. In 1912, President William Taft visited the house and in 1918, Thomas Edison lived there for several months as he worked on inventing new weapons for the war effort.

In 1946, the Little White House became Truman’s winter home and he proceeded to stay for 175 days. Always at work, the President held various meetings in the home, met with the Joint Chiefs of Staff, worked on the Marshall Plan and the Truman Doctrine and continually attended to his duties while enjoying the magnificent setting. A setting so magnificent, in fact, that Truman was known to spend an afternoon in town or out on the water fishing with friends. It's said that he was friendly with the locals and fit right into the island lifestyle.

Although several other United States Presidents visited the Little White House in the years that followed, it ultimately was named for Harry Truman because of his deep affection and adoration for the home and Key West.

Today, visitors from all over the world are able to get a glimpse into Truman’s life and times, see where he and Bess entertained guests, where critical meetings were held and how the business of our government was conducted in this lovely historic building.

In 1987, The state of Florida recognized the Little White House as a state historic site, guaranteeing permanent protection for Florida’s only Presidential Museum.

If you love history and the great outdoors, embark on an adventure like none other on board the Yankee Freedom III. A luxurious, state-of-the-art catamaran, docked in Key West, the Yankee Freedom III will transport you to the famous Dry Tortugas and Fort Jefferson National Park.

Just 70 miles west of Key West, the Dry Tortugas is a collection of secluded islands that boast a military fort, a national park, camping grounds, sandy beaches, crystal waters, coral reefs, fishing, snorkeling and so much more. See the historic Fort Jefferson and the place where Dr. Samuel Mudd was held prisoner due to his involvement in the assassination of President Lincoln. Come face to face with colorful fish and marine species that live on the coral reef. Spend the afternoon exploring the island, bird watching, having a picnic on the beach or soaking in the sun, gather the family and spend the weekend camping. The Dry Tortugas offers extraordinary experiences for people of all ages.

There’s no better way to get to The Dry Tortugas than on board the Yankee Freedom III which has been ferrying guests for more than 30 years. The spacious catamaran is the fastest way to get there and features an air-conditioned cabin, outdoor deck with comfortable seats, restrooms, showers and a snack bar that serves sodas, beer, wine and mixed drinks.

During the Civil War Key West, although the southernmost city in the country, was Yankee territory. Key West was the only place where you had to go north to fight for the South.

As you travel in comfort and style on the Yankee Freedom III, our experienced captain and crew will share with you fascinating facts and information about the Dry Tortugas, the wildlife and the natural surroundings of the area. Keep an eye out for playful dolphins swimming alongside of the boat and other friendly sea animals; the journey to the islands is half the adventure!

RESERVATIONS ARE REQUIRED!

Since the first Spanish galleons began to traverse the Florida Straits in the 16th Century, ships have wrecked along the treacherous reefs of Key West and the Florida Keys.

Wrecking and salvage – the recovery of wrecked ships and their cargos (as well as the rescue of their crews & passengers) - was the foundation of Key West’s economy throughout the 1800’s. By the mid 1850’s, Key West had become the richest city per capita in the entire United States – all due to the wrecking industry.

The Key West Shipwreck Treasures Museum celebrates the rich history of the Key West wreckers with two floors of shipwreck artifacts that include treasures from the Spanish fleets of the 16 & 1700’s, as well as a vast collection of pieces from the 1856 wreck of the Isaac Allerton. Guests can even lift a silver bar salvaged from the Spanish treasure galleon, Nuestra Senora de las Maravillas.

The museum itself is a recreation of 19th Century wrecker tycoon Asa Tift’s warehouse that includes a 65-foot lookout tower. A variety of audio-visual displays (including a below-sea-level theater) create windows into Key West’s past and allow our guests to experience life as it was for the brave souls who risked their lives to retrieve shipwreck treasures.

Storytellers in period costume bring history to life with tales of the wreckers and their daring rescues, ensuring a fun and fascinating experience for the entire family.

• Two floors of artifacts from shipwrecks spanning 400 years
• 65-foot lookout tower offers a spectacular view of the island
• Numerous audio/visual presentations including a below-sea-level theater
• Storytellers in period costume bring Key West’s rich history to life
• Lift a silver bar from the wreck of a Spanish treasure galleon!

Discover the beauty of Key West hidden on its shady side streets and lanes, beginning at the Key West Memorial Sculpture Garden, dedicated to many influential people in Key West’s history. During your stroll through old town, our guide will point out the blend of architecture, tropical foliage and culture that makes Key West unique. You’ll hear about the island’s fascinating history, from the U.S. Navy presence in 1823 to combat piracy through the heydays of the wrecking, sponging and cigar industries. You’ll learn how Key West developed into one of the wealthiest cities in the country, and how it declined into one of the poorest. Join us for a fact-filled historical tour full of heartfelt stories, experiences and anecdotes about our island life!  

One Whitehead Street • Key West, FL 33040 • (305) 292-8990   
May - October: 9:30am & 4:00pm
November - April: 10:00am, 2:00pm & 4:00pm 

Do you dare board the TROLLEY OF THE DOOMED?

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 - filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America.

EXCLUSIVE nighttime entry into one of the island’s haunted Civil War forts - once quarantine barracks for suffering soldiers left to die from yellow fever; now home to an eerie doll that can play tricks on you if you don’t play nicely. Our Ghost Host will add a pinch of humor to Key West's dark side with tales of deathly love, tragic endings, scores to settle, wrongs to right and ghastly folk – some so strange it will be hard to believe they’re true.

Exclusive! Visit with Robert the Doll.

Reservations are required. Space is limited for this very popular excursion, so DON’T DELAY!

Where: 501 Front St. • 305-29-GHOST (305-294-4678)
When: Nightly.
Tour Length: 1 hour and 30 minutes.

Now you can see the best of Key West like you never have before. The Southernmost Ducks Tour takes you on a 90-minute journey through the streets and across the waters of Key West—all in one tour!

The excitement starts at the corner of Front and Duval Streets—it’s here that you’ll board our incredible hydra-terra amphibious vehicle, created to travel from land to water and back onto land again without any interruptions or transformations. Coast Guard approved, safe and comfortable, the Duck provides a perfect view to all the sights for everyone on board without the need to ever leave your seat.

Once all of our guests are aboard, the Duck will begin to travel down Duval Street and our friendly, knowledgeable first mates will tell you all about the sights you’re seeing in the amusing, entertaining fashion that they are famous for. You’ll see the Hemingway House, the Key West Butterfly and Nature Conservatory, the Key West Lighthouse, Sloppy Joe’s Bar, Bahama Village and much more.

After traveling through the streets of Key West, the Duck will then head to the sea — and drive right in. Now our tour becomes a boat! We’ll cruise on by many of the most famous points of interest in Key West. You’ll see the Customs House, the historic seaport where Key West’s collection of tall ships are docked, including the state of Florida flagship - Western Union. We’ll pass by the Truman Annex Navy Base, Fort Zachary Taylor, the Nancy Foster Eco Discovery Center and Mallory Square. When you’re ready to witness all the best of Key West on land and sea — the Southernmost Ducks Tour is ready to take you!