key west historic tours

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.

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.

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.

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.

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.

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.

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

• 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

• 1-day tour of the Conch Republic
• One full loop through Old Town Key West
• Includes three stops
• Highlights marvelous sights, stories and entertainment

2-Day Trolley

• 2 consecutive days of free unlimited re-boarding

2-Day Conch Tour Train

• 2-consecutive day tour of the Conch Republic
• 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

• 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

• 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

• 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

Discover Amazing Tours in Key West

MUSEUMS & ATTRACTIONS

Step back in time and explore key west culture.

SHOPPING & DINING

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
• Shipwreck Treasure Museum
• Ghosts & Gravestones

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!

Get all the information you need

How long does the old town trolley tour last.

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!

What language are the tours in?

All of our tours are in English.

Where do I park?

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.

Are food and drinks allowed while on the tour?

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

Are dogs allowed on your trolleys and trains?

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.

Are your trolleys and trains accessible for individuals with wheelchairs and motorized scooters?

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.

Are your tours open every day?

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

What does the Conch Tour Train tour focus on?

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

Can I bring my stroller on board the trolley and train?

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.

Do you have public presentations at the Key West Aquarium?

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.

Do I have to take a tour at the Key West Aquarium?

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.

How much time should I expect to spend in the aquarium?

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

Is fishing allowed at Dry Tortugas National Park?

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.

Are there restrooms at the Fort Jefferson?

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.

Do cell phones work at Fort Jefferson?

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

How deep is the water in which we will be snorkeling at Fort Jefferson?

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

What’s the difference between Ghosts & Gravestones and other Key West tours?

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

Do we need reservations for the ghost tour?

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

Does the ghost tour run in the rain? / What's the inclement weather policy for the ghost tour?

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.

Is the ghost tour too scary for my kids? / Is the tour suitable for children?

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.

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• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

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Accessibility

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• www.toursofkeywest.com
• April 25, 2024

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Screen-reader and keyboard navigation.

• Screen-reader optimization: we run a background process that learns the website’s components from top to bottom, to ensure ongoing compliance even when updating the website. In this process, we provide screen-readers with meaningful data using the ARIA set of attributes. For example, we provide accurate form labels; descriptions for actionable icons (social media icons, search icons, cart icons, etc.); validation guidance for form inputs; element roles such as buttons, menus, modal dialogues (popups), and others. Additionally, the background process scans all of the website’s images and provides an accurate and meaningful image-object-recognition-based description as an ALT (alternate text) tag for images that are not described. It will also extract texts that are embedded within the image, using an OCR (optical character recognition) technology. To turn on screen-reader adjustments at any time, users need only to press the Alt+1 keyboard combination. Screen-reader users also get automatic announcements to turn the Screen-reader mode on as soon as they enter the website.These adjustments are compatible with all popular screen readers, including JAWS and NVDA.
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Key West home tours offer a peek into island lives

By: Author Bonnie Gross

Posted on Last updated: December 6, 2023

One of the great pleasures of visiting Key West is admiring the hundreds of historic homes that have been lovingly preserved and restored.

But few visitors get a peek inside those private homes.

Four weekends a year, however, the owners of some of Key West’s most interesting houses open their doors to visitors on Key West house tours to raise money for historic preservation on the island.

Winter 2023-24 is the 64th year that the non-profit Old Island Restoration Foundation (OIRF) hosted the Key West Home Tours. It is one of the oldest home tours in the country.

Tours are planned for:

• Friday and Saturday, Dec. 29-30, 2023: Home Tours “holiday style,” spotlighting five homes festively dressed for the season, including one with six holiday trees.
• Friday and Saturday, Jan. 12-13, 2024
• Friday and Saturday, Feb. 16-17, 2024
• Friday and Saturday, March 15-16, 2024

Tickets for each tour cost $55 per person ($45 for OIRF members) when purchased in advance through oirf.org/home-tours/ or $60 at the door on tour days. (You get a deal if you buy tickets for all four — $200 for nonmembers; $165 for members.)

All 2024 tours are set for 1-4 p.m., with visitors to travel between homes at their chosen speed via their own transportation. Each month’s tour features a different group of homes and a different experience for participants.

The tours feature houses reflecting the varied tastes and originality of their owners. Some showcase homes have been scrupulously restored. Others have been ingeniously renovated. Many have art collections and antiques.

Key West’s Old Town contains what is believed to be the largest predominantly wooden historic district in the United States with almost 3,000 structures. Many were constructed by shipbuilder-carpenters and cigar manufacturing barons in the 1800s, so the island’s architecture reflects the building styles and cultures of its early inhabitants.

How Key West house tours started

The first home tour was organized in 1960. It cost $2 per person and featured eight homes you could tour in three hours on a single Saturday afternoon. It was a very different era for Key West, according to Jean Shannon, a former board member of the OIRF.

“The Old Island Restoration Foundation was organized by handful of people who were really disappointed with what was happening to the island,” she said. “It was happening all over the United States, and it was called progress. Beautiful historic structures were being torn down.

“The organizers of the foundation realized they were losing their history,” she said. “If they didn’t do something, it would all be gone, replaced by gas stations and car dealerships.”

Shannon said the home tours were more than a fund-raiser: “We were opening people’s eyes to the fact that you could buy one of these homes and you could fix it up and you could save it.”

The appeal of Key West house tours today

Today, while few need to be convinced that Key West homes should be saved, education is still a major part of the tours, Shannon said.

“Once the 20 homes are selected, we research each home. We dig into the historic records and learn the background of each house. We want to give the visitor an idea of the history of island.”

It’s not all about educating visitors, however. It’s also about entertaining them.

“You’re walking through somebody’s home that has all sort of interesting features,” she said.  Volunteers are trained to point out details about the antiques, art works and architecture.

Sue Huffaker, a Key West resident for two decades who has attended more Key West Home Tours than she can recall, says that’s her favorite part of the tours – you’re not just seeing houses, in a way you’re also meeting the people who live there.

“It’s a form of voyeurism, I guess,” she said, laughing. “You get to see who people are. You see what’s important to them.

“Everybody puts out their most precious things and you get an insight into the person. This person is really family oriented with pictures everywhere. Or this person is into cooking.”

Her favorite thing, however, is to see the choice of art.

“You won’t see Cezanne or Picassos; many people have work by local artists in their homes and some of it is extraordinary,” she said. “I have found some of my favorite artists through the Key West Home Tours.”

Where does the money raised go?

The people who agree to open their houses for the home tours are motivated by helping to raise funds for historic preservation, Shannon said

The money raised by the home tours is used to make grants to local home owners and non-profits to fix up their buildings in the historic district. OIRF grants have helped preserve the Old City Hall, the Custom House, the Martello forts, the Key West Lighthouse, the Women’s Club, several churches, and more. Recently, grants helped fund repairs to historic buildings after Hurricane Irma damaged many.

The foundation also has preserved and maintains the Oldest House Museum and Gardens, 322 Duval St., which is open to the public to visit and tour.

Recruiting home owners to participate in the tour is an annual challenge. Volunteers who know about an interesting home will reach out to individuals and ask them to be part of the tour. Some years, celebrities such as children’s author Judy Blume have opened their homes.

Purchase tickets here .

Key West Home Tours logistics

Homes may be seen in any order and viewings may be split over two days. Since parking is challenging in Key West, it is best to bicycle or to combine walking with the free Duval Loop Bus. Here’s information and the route of the bus.

Resources for planning a Florida Keys vacation:

• Mile marker guide with dozens of stops to help make the most of your drive south.
• Florida Keys wildlife : Places to see animals
• Tiki bars:  Soak up the Keys atmosphere
• 12 great kayak outings in the Keys
• Top 10 pit stops on Overseas Highway
• Best beaches in the Florida Keys

Special places to explore in Key West

• Free things to do in Key West
• Key West on budget : Accommodations, restaurants
• Florida Rambler guide to the Lower Keys
• Key West Butterfly Conservatory : A tranquil stop
• Audubon House , a lovely refuge in Key West
• Historic Key West Seaport
• Historic Key West Cemetery  is full of stories
• Fort Zachary Taylor
• Key West chickens

All articles on FloridaRambler.com are original, produced exclusively for our readers and protected by U.S. Copyright law. Any use or re-publication without written permission is against the law.

This page contains affiliate links from which Florida Rambler may earn a sall commission when a purchase is made. This revenue supports our mission to produce quality stories about Florida at no cost to you.

The author, Bonnie Gross, travels with her husband David Blasco, discovering off-the-beaten path places to hike, kayak, bike, swim and explore. Florida Rambler was founded in 2010 by Bonnie and fellow journalist Bob Rountree, two long-time Florida residents who have spent decades exploring the Florida outdoors. Their articles have been published in the Sun Sentinel, the Miami Herald, the Orlando Sentinel, The Guardian and Visit Florida.

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Dave Cannon

Wednesday 22nd of November 2023

My brother-in-law's house was on the tour a few years back. He is a shipbuilder and historical architect. I will be there tomorrow, for the annual Thanksgiving potluck.

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Old Town Trolley Tours Key West 4.4

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 admission to the Sails to Rails Museum included
• FREE coupons worth up to $50 in discounts
• 100% satisfaction guarantee
• Exclusive stops and Key West attraction discounts

Ghosts & Gravestones

• 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
• East Martello Fort & Robert the Doll are no longer a stop on our tour

1-Day Conch Tour Train

• 1-day tour of the Conch Republic
• One full loop through Old Town Key West
• Includes three stops
• Highlights marvelous sights, stories and entertainment

2-Day Trolley

• 2 consecutive days of free unlimited re-boarding

2-Day Conch Tour Train

• 2-consecutive day tour of the Conch Republic

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

• 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

• 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

• 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

Why use Old Town Trolley Tours in Key West

• Riding around for over 30 years!
• All our tours are 100% live in real time - No pre-recorded narration
• The finest, most highly-trained and knowledgeable guides
• Unlimited hop-on & hop-off as often as you like all day long
• Proudly owned and operated in the United States

Old Town Trolley Tours is

Key west’s best hop-on, hop-off all day tour.

• Best view! Ride high above it all
• Every seat is the best seat!
• Most frequent service
• 13 convenient stops
• Exclusive stops
• Key West attraction discounts

Your Vacation… All Mapped Out For You!

• Trolley Routes & Stops
• Helpful information
• Points of Interest
• Shopping & Entertainment
• Restaurants & Bars
• And much more!

OLD TOWN TROLLEY TOURS

Old Town Trolley Tours

First tour starts at 9am.

Last tour departs from Mallory Square at 4:30pm.

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

For specific information, go to Ghosts & Gravestones schedule .

Reservations are required . Call for availability prior to making your e-ticket purchase:

(305) 294-4678

First tour starts at 9:00 am.

Last tour departs from Front Street at 4:30 pm.

For specific information, go to Conch Tour Train schedule .

What are the most popular stops on the Key West tour route? + -

We take great pride in providing an itinerary that showcases all the great aspects of each city during our tours. The most popular stops on our Key West tour include the Historic Seaport, Duval Street, and the Southernmost Point.

How long is the Key West tour route from start to finish? + -

Our Key West tour is 13 miles long and averages 90 minutes from start to finish, but our hop-on, hop-off tour is designed for you to hop off at any stop, explore a Key West attraction or neighborhood, and hop back on when you are ready to resume your Key West sightseeing experience.

Do I have to start at stop #1? + -

You may start your Old Town Trolley Tour at any of our convenient stops. Click on Map and Stops to see a list of our stops with information about the attractions and points of interest at each stop.

What neighborhoods does the tour visit? + -

The Key West tour travels through Bahama Village, Old Town, Truval Village, and the Historic Seaport.

Does the tour run on holidays and holiday weekends? + -

Our Key West tours run 364 days per year (365 in leap years). We’re closed on the Saturday of Fantasy Fest (October).

How often do tours run throughout the day? + -

Old Town Trolley Tours of Key West operates the city’s largest fleet of sightseeing vehicles, and this allows us to pick up and drop off more frequently than any other trolley company. The frequency of the trolleys depends on the time of the year, traffic, and weather conditions.

How do I get to Mallory Square? + -

One of the must-visit places in Key West is Mallory Square, which is famous for its stunning sunsets and street performers. Old Town Trolley is unique and fun and the most convenient way to get to Mallory Square. The tour takes you through the winding streets of Key West, past colorful houses, lush gardens, and sparkling waterways. The tour guide gives you a brief history of the city’s landmarks, including the Ernest Hemingway Home & Museum, the Southernmost Point, and the Truman Little White House. The trolley takes you to the entrance of Mallory Square, where you can get off and start exploring on foot. You can take a leisurely stroll along the waterfront, admiring the breathtaking views of the sea and the distant horizon. You will also find many street performers here, who entertain visitors with their unique talents, including magic tricks, fire dancing, and acrobatics.

What is the best way to tour Key West? + -

With so much to see and do, it can be challenging to explore the city in a short amount of time. Luckily, there is an easy and convenient way to tour Key West — with a Key West Old Town Trolley Tour. Sit back and relax while the trolley takes you to all the major sites and attractions in the city. With its open-air design, you can enjoy the warm Florida breeze and scenic views while learning about the city’s rich history from knowledgeable tour guides. You can visit popular landmarks such as the Ernest Hemingway Home & Museum, Harry Truman’s Little White House, and the famous Southernmost Point buoy. You can take advantage of packages that include admission to the Truman Little White House, the Key West Aquarium, and the Key West Shipwreck Treasure Museum.

How long does it take to visit Key West? + -

The short answer is that it depends on what you want to see and do. If you’re looking to get a taste of the excitement, two days may be enough. You will have ample time to explore the many museums, art galleries, shops, and restaurants that this beautiful city has to offer. When you’re on a tight schedule and want to experience Key West in a day, Old Town Trolley Tour is the perfect solution for you. The beauty of this tour is that it covers more than 100 points of interest, making it easy for you to hop on and off as you please.

What are the most famous attractions? + -

If you’re planning to visit, don’t miss out on the chance to discover the most famous attractions in Key West. The must-see attractions in Key West include the Ernest Hemingway Home & Museum, the Key West Butterfly & Nature Conservatory, the Historic Seaport District, and the Key West Lighthouse. Additionally, make sure you visit the Southernmost Point buoy, stroll down Duval Street, and enjoy a slice of Key lime pie! The city is rich in history and culture, and an Old Town Trolley Tour is a perfect way to experience and explore the city’s famous landmarks. The attractions mentioned are some of the top-rated tourist destinations that you should include in your itinerary. Don’t miss the chance to visit these fantastic places and see the colorful and lively locations that have captured the hearts of tourists worldwide.

Which street has the most things to do in Key West? + -

If you are visiting Key West, you will want to take a stroll down the lively and vibrant Duval Street. This bustling street is the heart of the city, a veritable hub of tourist activity. It is a must-visit destination that offers something for everyone. From dining and shopping to nightlife and fascinating attractions, Duval Street has it all. The street is home to several historic landmarks, shops, restaurants, and entertainment spots. You can explore the street on foot, by bike, or by taking a ride on the famous Conch Tour Train or Old Town Trolley Tour. The street is home to several popular tourist attractions, such as Crowne Plaza La Concha, Sloppy Joe’s Bar, Kermit’s Key West Key Lime Pie Shoppe, and the Key West Butterfly and Nature Conservatory.

What is the most beautiful part of Key West? + -

The first must-visit location that everyone should see in Key West is the Southernmost Point buoy. This famous landmark is located at the southernmost point of the continental U.S. The buoy has become an iconic spot due to its colorful appearance and its proximity to Cuba, just 90 miles away.

Another stunning vista to experience is Fort Zachary Taylor Historic State Park, located on the southern tip of Key West. Fort Zachary is favored for its beautiful beaches and striking views of the horizon. This lovely spot is a perfect place to enjoy some relaxation, taking in the beauty of the surroundings.

The Old Town Trolley Tour is perfect for travelers who want to explore and witness the beauty and history of the city.

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Please note: After your purchase is confirmed you will receive a complete tour itinerary with check-in time, location and what to bring.

Historic Key West Walking Tour

Restrictions

• 1-2 Hour Walking Tour
• Get an Overview of Key West's History
• See Diverse Architectural Styles
• Learn About U.S. Navy Influences
• Available November Through May

Starting with the era of wrecking through the eras of sponging, cigar manufacturing, US naval influences, Key West has witnessed many different groups of people come and go, each leaving their own marks on this unique island. On our two-hour Historic Key West Walking Tour, you will be able to see the many historical influences that have created the Key West of today.

The walking tour has a few main themes. The first is architecture. The historic Old Town district of Key West contains the largest collection of wooden frame buildings in Florida. There are over 3,000 historic homes and historic sites in this area, 300 of which are registered under the National Register of Historic Places. Another predominant theme of the tour is the naval influence of Key West. See some of the spots that were important in the US military and learn about other maritime influences.

While walking through the narrow streets of Key West, you will also be treated to the soothing scents of various flowers such as orchids, gardenias, and bromeliads. All tours feature an entertaining and knowledgeable tour guide who will fill you in on the history and facts of the stops and sights you will see along the way.

Is there parking available? Parking is available at Mallory Square or The Westin Parking garage.

How much walking is involved? The tour is approximately 1 1/4 miles.

It is your responsibility to make sure you are aware of and understand all restrictions pertaining to this tour before booking online or over the phone. It is your responsibility to ensure that you are medically qualified and within any limits listed below in order to participate in this activity. No refunds will be given to those who reserve a spot and can not participate due to the restrictions listed below. For more information please read our cancellation policy and terms and conditions page or call our staff with any questions regarding your ability to participate.

• Tour only operates from November through May. June through October this tour is closed for the Summer months.
• Schedule is subject to change. Please call the number on your E-Ticket upon arriving in Key West to re-confirm details for your tour
• Limited spots available and reservations must be made at least 48 hours in advance

Found a better price online? We will price match it. Just call our Activity concierge and ask for our price matching special.

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Key West HISTORIC MARKER TOUR

Captain george carey house, the key west woman's club, casa antigua, james haskins house, la concha hotel, the oldest drug store, the southernmost house, the oldest house, william wall warehouse, dr. joseph yates porter house.

The Truman Little White House

Harry S. Truman

Little White House

Florida's Only Presidential Museum

VIP White Glove Tour

Get the presidential treatment with our exclusive VIP White Glove Tour. This unique experience will give you first-class access and amenities, including a rare glimpse behind the scenes and a ride in President Truman’s 1949 Lincoln Cosmopolitan Limousine.

Museum Tours

Take a guided tour through the former home turned museum of President Harry S. Truman. Explore where the man of his time lived, worked, played, and held important government meetings in this delightful journey through American history.

Weddings & Private Events

We are still taking wedding & private event inquiries! Please call us at 305-671-9199 or fill out our form.

Ask us about getting a virtual tour of our space!

Memberships & Donations

We are still taking memberships & donations at this time. You can submit a one-time gift or recurring gifts. If you donate $100 or more, you become a member with benefits!

Presidential Timeline

1944 - Nominated To Run For Vice President

In 1944, the Democratic party leaders considered Vice President Henry Wallace too unpredictable to serve another term under President Franklin D. Roosevelt, whose health had visibly declined during the Second World War. The party then turned their attention to the U.S. Senator, Harry S. Truman from Missouri, who was nominated to be President Roosevelt’s running-mate for an unprecedented fourth term re-election.

1944 - The GI Bill

In 1944, Harry S. Truman helped introduce the GI Bill, widely regarded as one of the most effective social policy programs in U.S. history. The GI Bill gave millions of soldiers returning from World War II the opportunity to enroll in college or job-training programs. It also helped grant low-interest loans towards the purchase of new homes.

1945 - Truman Becomes 33rd President

The first inauguration of Harry S. Truman as the 33rd President of the United States was held at 7:00 pm on Thursday, April 12, 1945, in the Cabinet Room at the White House in Washington, D.C., following the unexpected death of President Franklin D. Roosevelt earlier that day. Harry S. Truman had only served as Vice President for less than three months prior.

1945 - The Atomic Bomb

Truman’s presidency is most often defined by his decision to drop the atomic bomb to end World War II that ultimately saved both Allied and Japanese lives.

1945 - VE Day

On May 8, 1945, Harry S. Truman announced to the American public that Germany had surrendered, signaling the beginning of the end of World War II and is known as VE Day. Ironically, it was also the President’s 61st birthday. It would take until August 14 before Japan officially surrendered ending World War II.

1946 - 1964 The Postwar Baby Boom

The postwar “Baby Boom” (1946 to 1964) was the largest generation in history. After years of depression and war, Americans, quite simply, were having more children. In 1940, American families had, on average, 2.6 children. By 1950, that number had jumped to 3.2. The baby boom was only one of the massive changes underway in the structure of the American family during the years immediately following World War II.

1947 - National Security Act

On July 26 , 1947, President Harry S. Truman signs the National Security Act, which becomes one of the most important pieces of Cold War legislation. This led to a reorganized structure of the U.S. armed forces following World War II. It created the office of Secretary of Defense, the Central Intelligence Agency (CIA), the National Security Council (NSC), as well as separate departments for each branch of the armed forces.

1947 - Taft-Hartley Anti-Labor Legislation

The Labor-Management Relations Act of 1947, better known as the Taft–Hartley Act, is a United States federal law that restricts the activities and power of labor unions. It was enacted by the 80th United States Congress over the veto of President Harry S. Truman, becoming law on June 23, 1947.

1947 - 'Containment' - A New Foreign Policy

The Truman Doctrine was announced to Congress by President Harry S. Truman on March 12, 1947, and further developed on July 4, 1948. This order pledged to contain the communist uprisings in Greece and Turkey by establishing that the United States would provide political, military and economic assistance to all democratic nations under threat from Soviet communism.

1947/1948 - The Marshall Plan

In 1948, President Harry S. Truman signed the Economic Assistance Act, which authorized the creation of a program that would help the nations of Europe recover and rebuild after World War II. Most commonly known as the Marshall Plan, it aimed to stabilize Europe economically and politically so that European nations would not be tempted by the appeal of communist parties.

1948 - Dewey Defeats Truman

In 1948, Truman won reelection. His defeat had been widely expected. His famous “Whistlestop” campaign tour through the country has passed into political folklore, as has the photograph of the beaming Truman holding up the newspaper whose headline proclaimed, “Dewey Defeats Truman.”

1948 - Executive Order 9980 & 9981

On July 26, 1948, President Harry S. Truman issued two of his most important Executive Orders, 9980 and 9981, desegregating the federal workforce and desegregating the armed forces. However, it could not be to get votes as there were not that many registered black voters.

1948 - Key West Accord

In 1948, Joint Chiefs of Staff met at the Truman Little White House and merged the Departments of War and the Navy, creating the Key West Accord. This was a major step toward defining the differences between the military services over their respective roles and missions.

1949 - NATO is Established

On July 25, 1949, President Truman and Secretary Acheson signed the Instrument of Accession, making the United States a founding member of the North Atlantic Treaty Organization (NATO), a mutual defense pact aimed at containing possible Soviet aggression against Western Europe. The newly created Alliance was composed of 12 different nations, including the US.

1950 - Census, Even the President Gets Counted

In 1950, another census year, the Truman family was vacationing in Key West. While on the island, the census caught up with the President and his family and they were interviewed on the lawn. As the picture shows, the Truman family, especially Mrs. Truman and Margaret enjoyed the line of questioning directed at the President.

1951 - Enacted the Civil Rights Executive Order

In 1951, President Harry S. Truman introduced another Executive Order which established the Committee on Government Contract Compliance. Truman created the committee with legislation passed by Roosevelt in 1941. Roosevelt’s legislation made discrimination with the federal government or defense industries based on race, color, creed, or origin illegal.

1953 - Korean War Ends

In 1950, President Harry S. Truman announced that he was ordering U.S. air and naval forces to South Korea to aid the democratic nation in repulsing an invasion by communist North Korea. On July 27, 1953, after two years of negotiation, an armistice was signed, ending the war and reestablishing the 1945 division of Korea that still exists today.

1953 - Truman Retires

In January 1953, Harry S. Truman left the Presidency and retired to Independence. He delighted in being “Mr. Citizen,” as he called himself in a book of memoirs. For the nearly two decades of his life remaining to him, he spent his days reading, writing, lecturing and taking long brisk walks. He took particular satisfaction in founding and supporting his Library, which made his papers available to scholars, and which opened its doors to everyone who wished to have a glimpse of his remarkable life and career.

Tickets & Packages

Truman Little White House Museum Tour

• Guided tour of Florida’s only presidential museum
• Knowledgeable guides share fascinating stories of Harry S. Truman’s time here
• Visit where Eisenhower recuperated from his heart attack in 1956
• Thomas Edison resided here during World War I

Truman Little White House VIP White Glove Tour

• Exclusive group tour of up to 6 guests
• Behind the scenes glimpse of Truman's custom and original bar
• Exclusive photo opportunity at Truman's desk and custom-built poker table
• Access to exclusive Presidential exhibits in the White Glove Lounge
• Complimentary refreshments & keepsake souvenir included
• Enjoy a VIP ride in one of President Truman’s limousines

Museum Tour, Trolley Tour & Shipwreck Museum Package

• Exciting, fully narrated tour of Key West
• 1 day of free unlimited re-boarding / hop on & off
• FREE admission to the Sails to Rails Museum included with ticket
• Discover the world of shipwrecking 150 years ago
• Hear the story of the Isaac Allerton shipwreck

Museum Tour, Conch Tour Train & Shipwreck Museum Package

• Ranked Top 20 things to do on Trip Advisor
• Full color map and discount coupons for attractions, restaurants and shopping with every ticket

Presidential Logs

Historical documents.

The eleven trips of President Harry S. Truman were recorded in official trip logs. Often regarded as mere souvenirs for family and staff, a more careful reading reveal clues as to the working of the president in Key West.

Truman’s Original 1950 Limousine

The 1950 Cosmopolitan Lincoln Limousine from President Harry Truman’s presidential fleet is now at the Little White House. The Limousine will be a part of the new White Glove Tour offered by the Little White House Museum and the Key West Harry S. Truman Foundation. The tour will include a private look at the Harry S. Truman Little White House, a ride in the presidential limousine and a final white glove opportunity at the Foundation Headquarters in Building 21.

Can I make a donation?

There are several ways you can leave your mark on the Little White House. Funds are always needed and can be designated for operations, exhibits, restoration, educational outreach, capital campaign or endowment. If you’re interested in supporting the Truman Little White House, there are several ways you can make a donation, including online, by phone, or in person. All donations are tax-deductible and help support the maintenance, preservation, and educational programs of the Truman Little White House. Donations to the Truman Little White House go towards a variety of operations, including preserving the historic building, providing educational programs, and improving visitor experiences. Your contribution is critical to the operations of the museum and the preservation of the building.

How can I attend Foundation Events?

Members receive notifications first for programs and invitations to events.

What are the Foundation membership benefits?

Today, the Little White House is a museum dedicated to preserving the history of the property and the men who called it home. One of the most beneficial ways to support the mission of the Truman Little White House is to become a member.

As a member, you’ll get unlimited Access to Tour and Events, Invitations to Special Events, Discounts on Museum Store Merchandise, and Discounts on Admission Fees for Friends and Family. Join today and become a part of preserving the history of one of America’s most unique and historic properties!

Who was Harry S. Truman?

He was the 33rd President of the United States and served as Commander-in-Chief from 1945 to 1953. Truman was born in Missouri in 1884 and grew up in a family that often faced financial hardship. Despite his lack of formal education, Truman was a voracious reader, and he eventually went on to graduate from the University of Missouri in 1925. Prior to becoming President, Truman was a successful Missouri politician, serving as a county judge, US Senator, and Vice President under Roosevelt. Truman played a critical role in shaping the post-war world, including the establishment of the United Nations and the Marshall Plan for European recovery as well as supported several key initiatives, including the Fair Deal, which sought to promote civil rights, minimum wage laws, and labor protections. Harry S. Truman was an important president who helped shepherd America through a tumultuous period in its history. His legacy is notable for the significant domestic and foreign policy initiatives he implemented, as well as his dedication to service and his no-nonsense approach to politics.

What is Harry S. Truman best known for?

Harry S. Truman served as the 33rd president of the United States from 1945 to 1953. His presidency was marked by some of the most challenging times in American history, including the end of World War II and the beginning of the Cold War. 

One of the most significant events of Truman’s presidency was the end of World War II. Truman made the call to drop atomic bombs on Hiroshima and Nagasaki, ultimately leading to Japan’s surrender and the end of the war. While controversial, Truman argued that this decision saved American lives and was ultimately necessary to end the war quickly. 

The Marshall Plan is another significant achievement of Truman’s presidency. It was designed to provide economic assistance to Western Europe, helping to rebuild after the devastation of World War II. The plan was a crucial part of America’s recovery and helped to maintain political stability across Europe. The Marshall Plan demonstrated Truman’s commitment to international leadership and set the stage for America’s continued involvement in global events.

The Truman Doctrine established that the United States would assist any country threatened by communist forces or ideology. The Truman Doctrine demonstrated Truman’s firm stance on communism, and his willingness to act when necessary to protect American interests.

Truman was also a vocal advocate for civil rights. He established a Presidential Committee on Civil Rights, which recommended significant reforms to address discrimination and racism in America. Truman also issued executive orders desegregating the military and federal agencies. Truman’s support for civil rights was a significant step forward for American society, and his efforts paved the way for the Civil Rights Movement in the following years.

After leaving office, Truman created the Truman Library and Museum to act as a repository of presidential papers and information about his presidency. The library contains over 15 million pages of documents, and it’s one of the most significant historical archives in the country. The Truman Library is a testament to Truman’s belief in the importance of preserving history and ensuring that future generations can learn from the past.

What was the Marshall Plan?

The Marshall Plan was a comprehensive plan to help rebuild the economies of Europe, which had been devastated by World War II. The plan was proposed by Secretary of State George Marshall in 1947 during President Truman’s presidency. The plan provided economic aid to 16 European countries, including the United Kingdom, France, Italy, and Germany. The first meeting of the Marshall Plan’s European Advisory Commission held in 1947 was in Truman Little White House.

Did Harry S Truman live in Florida?

Yes! During his presidency, Harry S Truman spent 175 days in the Truman Little White House in Key West, Florida. This historic site was originally built in 1890 as the naval station’s command headquarters. It was later converted into a winter White House for President Truman and his family.

How many trips did President Truman make to the Little White House?

Truman made 12 visits to the Little White House throughout his presidency. Here is a record of his logs. Today, visitors can walk the same grounds that Truman did and gain insight into the challenges that he faced, both personally and politically.

How much time did Truman spend in Key West?

Between 1946 and 1952, Truman spent a total of 175 days residing and working at the Little White House. Step back into the era of Harry Truman and explore his personal belongings, including the living quarters where he and Bess resided, original furnishings, personal effects, and much more. Additionally, you’ll have the opportunity to see the rooms where Truman held meetings with the Joint Chiefs of Staff, worked on the Marshall Plan, and penned the Truman Doctrine.

What did Truman do in the Little White House?

The president had various duties during his stay, including attending to important state affairs and plowing through the numerous papers that piled up on his desk. It is said that he composed some of his most critical speeches in the living room of this house. During his time in Key West, the president spent time with family, friends, and advisors, but he also utilized the advanced communication system installed at the house to keep in touch with his top advisors in Washington.

Who lived in the Little White House?

Built in 1890, this beautiful structure was initially the command headquarters of the naval station during the Spanish-American War. It wasn’t until 1946 that it was converted into the winter residence of the 33rd President of the United States, Harry S. Truman.

Other well-known politicians and celebrities also made their way to Key West to visit the house. Among them were former President Dwight D. Eisenhower, British Prime Minister Winston Churchill, and even Harry Truman’s wife’s Uncle Eddie.

William Howard Taft, the 27th President of the United States, made use of the Little White House when he visited in 1912. He’d arrived to inspect the world-renowned Panama Canal, built during his presidency.

The Little White House was also used when President John F. Kennedy chose it as his Winter White House in 1961. Kennedy was looking for an escape to the Florida Keys. The president spent a whopping 45 days in the House before he had to attend to important matters in Washington.

What presidents have stayed at the Little White House?

President Franklin D. Roosevelt was the first to stay at the Little White House in 1932, and since then, many presidents have followed in his footsteps. President Dwight D. Eisenhower stayed at the Little White House in 1955 and 1956 during his terms in office. President John F. Kennedy visited in 1962. In the 1980s, Key West underwent a transformation and became a tourist destination, where President Jimmy Carter and President Bill Clinton sought relaxation.

Why did Truman say “the buck stops here”?

President Harry S. Truman became renowned for his declaration, “the buck stops here,” emphasizing the President’s responsibility to make final decisions on crucial national matters. Truman often mentioned the desk sign in public statements. He diligently worked daily at his desk in the living room of the Little White House, where the iconic “The Buck Stops Here” sign can be seen.

What did Thomas Edison do during WWI?

During World War I, Edison was asked to help the war effort by using his expertise to develop new technologies. He was appointed to the Naval Consulting Board and worked with the Navy to develop new weapons and technologies. One of Edison’s most notable contributions during WWI was the development of the Truman Little White House in Key West, Florida. This facility was used to develop and test new weapons and technologies for the Navy. Edison was also involved in the development of the first submarine detection system, which was used to detect enemy submarines.

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Best Historic Homes in Key West

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Welcome to the historic homes of Key West! This vibrant yet relaxed city is full of illustrious houses and buildings that have served as homes to famous authors, musicians, adventurers and more. From architectural gems built in the late 1800s, including Ernest Hemingway’s famous Spanish colonial estate, to modern beachfront mansions, discover what makes Key West’s real estate so special. Nestled at the southernmost tip of Florida lies Key West, a vibrant and colorful city teeming with a blend of cultures and a captivating history. Characterized by its whimsical architecture, sun-drenched streets and lush tropical gardens, the island city offers a picturesque setting for anyone seeking an unforgettable and authentic experience. Often referred to as the “ Conch Republic ,” Historic Key West has long been a haven for those with adventurous spirits, from the likes of legendary writer Ernest Hemingway to treasure hunter Mel Fisher. As you wander through the bustling heart of Old Town, you can’t help but be enchanted by the striking murals and sculptures gracing the city’s lively streets, reflecting the artistic soul and Caribbean influence that has shaped Key West over the years. A destination like no other, a Key West historic home tour takes you on a rich journey through its cultural tapestry and exciting past.

Harry S. Truman Little White House

Visiting the Harry S. Truman Little White House in Key West, Florida, is an amazing way to feel connected to history and learn something meaningful while having a great time with family or friends. The historic Key West home was originally built as the command center for Fort Taylor during the mid-1800s. This building has seen much of American history pass by its doors, including some of the oldest maritime areas of the state and families who settled here for centuries. Its use changed in 1910 when it became a naval station and then eventually was reborn as a vacation home for President Truman between 1946 and 1952 – becoming known all around America as the Little White House. All these years later, visitors can witness firsthand what life must have been like for President Truman during his regular visits to one of the most iconic places in all of Florida!

Ernest Hemingway Home and Museum

Step back in time and immerse yourself in the world of the great American writer Ernest Hemingway by touring the Hemingway Home and Museum, a slice of literary history nestled in the heart of historic Key West, Florida. As you wander through each sun-soaked room, you’ll witness the space where Hemingway’s writing process came to life, creating timeless masterpieces. Listen to fascinating stories that thread together Hemingway’s dynamic personal and professional life, including his passion for boxing, fishing and the arts. And, of course, no visit would be complete without encountering the famous six-toed cats! These feline treasures, descended from Hemingway’s original cat, Snow White, continue to roam the property, captivating visitors with their charm and unique extra digits. The Ernest Hemingway Home and Museum offers an unforgettable experience to both fans of Hemingway’s work and curious travelers alike.

Audubon House

Welcome to the Audubon House in Key West, where history, nature and family fun come together for a truly memorable experience. Located in the heart of Old Town, near Duval Street, the Audubon House is one of America’s most popular tourist attractions. The house stands as a testament to one of America’s greatest naturalists, John James Audubon, and his visit to the Conch Republic in 1832. Explore the Key West historic home and learn about the diverse flora and fauna that inhabit this paradise! Explore historical artifacts from some of Key West’s earliest pioneering ancestors, or take a tour guided by historians or official docents who have dedicated themselves to preserving this highly acclaimed landmark since 1960. The historic Audubon House is a must-see when exploring historic Key West homes!

Tennessee Williams’ Home

Have you ever dreamed of visiting the home of one of our nation’s most iconic playwrights? If so, then a visit to Tennessee Williams’ home in Key West, Florida, is an absolute must-see. Located on Whitehead Street, the iconic Tennesee Williams’ home provides visitors with an unparalleled glimpse into Williams’ life and career through memorabilia and interactive experiences. From discovering his writing process to hearing stories about his time in paradise, this historic Key West home offers something for every kind of tourist or traveler!

Key West Woman’s Club

319 Duval Street still stands as an enduring example of classic Key West architecture, with gingerbread fretwork and a broad veranda. The Woman’s Club has carefully restored the home to its original grandeur, complete with beautiful hardwood floors, period furniture, and even Eleanor Hellings’ original piano. Group tours are available by request and provide visitors the opportunity to learn more about Captain Hellings’ illustrious career as a businessman and sailor, as well as the fascinating history of the home. Visitors can also explore the Key West Woman’s Club Library on-site, which serves as a valuable local resource containing archives from throughout Monroe County’s rich past. If you’re seeking an unforgettable Key West historic home tour, the Key West Woman’s Club is a must-see. With its unique architecture, historical artifacts and stories, it’s truly an unforgettable experience.

Amsterdam’s Curry Mansion Inn

Amsterdam’s Curry Mansion Inn is a beautiful, historic attraction, which will surely make your Key West historic home tour itinerary. Built by Milton Curry in 1869, the lavish Georgian Revival mansion stands as a testament to William Curry’s astounding success as Florida’s first self-made millionaire! The outside of the mansion is decorated with Birdseye maple bark to give it a unique and elegant look. Now, visitors can stay at the 28-room bed-and-breakfast or take a guided tour of the mansion. Whether you’re interested in seeing the historical architecture up close or staying overnight, there is something for everyone at Amsterdam’s Curry Mansion Inn. Come experience this piece of Florida history for yourself and make memories that will last a lifetime!

The Artist House

The Artist House is just as beautiful and unique! Built in the 1890s, this two-story Colonial Queen Anne-style home at 534 Eaton Street was once the studio of painter and author Eugene Otto. It now serves as a seven-room bed-and-breakfast full of charming touches, such as lilac-colored shutters, gingerbread trim, claw-foot tubs, fireplaces and private balconies. The highlight of the house is certainly the octagon-shaped turret, which has been turned into a stylish guest suite. Whether you’re interested in staying at this beautiful historic home or simply taking a tour to marvel at its showy details, the Artist House is a must-see historic Key West home.

What are the oldest homes in Key West?

Key West is home to some of the most historic homes in America. We’ve put together a list of some of the oldest houses in Key West that are still standing today:

Ernest Hemingway Home Tennessee Williams’ Home The Little White House Audubon House

Who lived in the Hemingway House?

Hemingway, his wife Pauline and their two sons lived together in the house until 1940.

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The Fascinating History of Key West, Florida

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As you know, I absolutely love visiting Key West! I’m happiest when soaking in the city’s tropical vibes, listening to Jimmy Buffett songs, and feeling the stress melt beneath the country’s southernmost sunset.  Key West  has a special place in many people’s hearts as a city for misfits, a place for big dreamers who want solitude and freedom. But how did it come to be? Let’s dive into the history of Key West, Florida. 

The History Of Key West

The city has a wild history filled with stories of adventure, mystery, and comedy. Key West’s history has made it one of the world’s most famous island tourist destinations, and its colorful people continue the long tradition of fun in the sun.

As they say, Key West isn’t so much a place as a mindset.  

Historical & Fun Facts About Key West

In this post, I want to highlight some of the more fascinating facts about the history of Key West. I’m touching on lesser-known facts you may not already know. Trust me, there are a lot of them hidden in this eccentric paradise!

And knowing all of these great tropical tidbits of information will ensure you appreciate this charming community on your next trip! 

Key West Was Originally Called “Bone Island”

An obscure fact about  Key West  is that centuries ago, it was called “Bone Island.” The ancient fishermen visiting the island found large amounts of human remains there. It turns out that ancient indigenous peoples used the island as a communal burial site.

The Island Was Sold Twice

It’s true! In 1790, Spaniard Don Juan de Estrada received the island through a land grant from the Spanish government. He then sold it to Juan Pablo Salas in 1815.  

Salas was so excited to make a profit on the island that he sold it twice! First, to John Simonton, for $2,000 in 1821. And second, in 1822, to an attorney named John Strong. It took many years for ownership to get straightened out, and Simonton was declared the rightful owner in 1828.

Only One Of Key West’s Founding Fathers Lived There

Of the four founding fathers heralded as the original settlers and developers of the city, only one spent a significant amount of time living there. Pardon C. Green lived permanently on the island in the early and mid-19th century. While in Key West, he started a company, was a city council member, and briefly served as mayor.

Key West Is One Of The Warmest Places in The Country

Key West, Florida, is the southernmost point in the United States. You can see a famous bright red buoy marking this point at the corner of South and Whitehead Streets.  

It’s one of the sunniest and warmest places in the US, with 260 annual sunny days and temps ranging from 65°F to 89°F. Key West also has the warmest ocean water of any place in the United States in the winter and averages 75°F to 77°F.

Key West Is Near A Giant Barrier Reef

Key West sits on the only living coral barrier reef in the US. Several related reefs extend 350 miles from the Dry Tortugas west of Key West to the St. Lucie Inlet near Miami. Coral reefs are home to many marine life and a unique underwater ecology. Almost 1,400 species of aquatic plants and animals live in the Florida Reef.

Key West Is Closer to Havana than Miami

Key West  is closer to Havan, the capital of Cuba, than Miami, Florida. Key West is so far south in Florida that it’s very close to Cuba, which lies only 95 miles off-shore. Due to their proximity, Key West and Cuba often share common elements of their culture, people, and economy.  

Ernest Hemingway Loved Key West

The Nobel Prize-winning author Ernest Hemingway lived on the island during the middle of the 20th century. You can still tour his home and see his amazing six-toed cats. They all descend from “Snow White,” a six-toed cat Hemingway received as a gift. The cats have a genetic mutation that gives some cats six or more toes! This trait is reliably passed down to each generation of newborn kitties.  

At the Hemingway House, you can also see the penny he placed in the wet cement of his pool. It was the first pool built in a 100-mile radius and was so expensive he put the penny there and exclaimed, “You can take my last penny!’ when he saw the construction bill.  

I love reading about the history of Key West as it relates to Hemingway!

A Lot Of Famous People Have Lived In Key West

For a small town with a population of only 26,000,  Key West  boasts an astounding number of famous inhabitants over the years.  They all contributed to the history of Key West in one way or another!

A short list includes author Judy Blume, poet Wallace Stevens, author Shel Silverstein, playwright Tennessee Williams, President Harry S. Truman, author Earnest Hemingway, singer Jimmy Buffet, NASCAR Driver Dale Earnhardt Jr., poet Robert Frost, author Truman Capote, fashion designer Calvin Klein, and treasure hunter Mel Fisher.

Key Lime Pie Was Invented In Key West

Was Key Lime Pie first made in Key West? Legend has it that in the late 1800s, Key West sponge fishermen called “Hookers” would make homemade food by pouring sweetened condensed milk with lime juice over Cuban bread. Wives of these men began baking it into a pie crust to create a sweet dessert.  

Sarah Jane Lowe Curry, the daughter-in-law (other legends say she was his cook) of Florida’s first millionaire, started serving the dish to people who came to her house. Sarah, or “Aunt Sally” as she was known, became the mother of the Key Lime Pie. Soon after, the pie was being served in restaurants everywhere.  

Whether or not you believe these stories, the truth is that Key Lime Pie is a famous Key West dessert, and you can find these delicious pies served at many of the city’s restaurants.

Chickens Walk The Streets of Key West

Yes, Key West has a lot of chickens wandering around the city! Chickens are the original inhabitants of the keys. Early locals lived alongside them and raised them for eggs or meat.  

The ancestors of these birds have become the official Key West Gypsy chickens, and they proudly and unabashedly prowl the streets of  Key West . Seeing these fowl reminded me of Ybor City and their resident chickens!  

In 2004, the city hired a professional bird catcher. But, the citizens did not receive it well, and the position was eventually eliminated. Now, you can enjoy the Gypsy chickens, and they get to live a peaceful life as a tourist attraction in one of the nation’s top vacation destinations!

Key West Is The Birthplace of Pan Am Airlines

Pan American Airlines started in Key West, Florida, in 1927. The location is now home to First Flight, a restaurant and bar. But the aviation history of Key West doesn’t stop there!

Known as The Amazing Race, in 1913, a competition started between two early aviators to see who could make the first flight from Key West to Havana, Cuba.

Then, in 1920, Aeromarine Airlines flew America’s first official international airmail service, once again between Key West and Havana.

President Truman Made A “Little White House” in Key West

In 1946, President Harry S. Truman began using a home in Key West as a winter retreat and operated it as a remote “White House .” He stayed in the home intermittently for 175 days over 11 visits. This house had earlier famous visitors, including President William Taft and Thomas Edison.  

Today, the home is the Harry S. Truman Little White House. It’s Florida’s only presidential museum. At the museum, you can tour the home, see Presidential memorabilia and photos, and learn the history of Truman’s presidency and its importance to Key West. The house is set within a beautiful botanical garden filled with tropical flora.  

I visited the museum, and I highly recommend it! Not only did we learn about President Truman while on the tour, but we also learned a great deal about the history of Key West.

Key West Loves To Celebrate

For a small island,  Key West  has a tremendous capacity to party! It’s known for several famous annual festivals that attract people from all over the world.  

The Conch Republic Independence Celebration (April 20-29, 2024) starts with a conch-blowing contest. It continues with boat races, a parade on Duval St, victory pirates, and a Pirates Ball and Costume competition.  

The Key West Songwriters Festival (May 1-5, 2024) showcases veteran and new songwriters who take the stage to mesmerize audiences with music and storytelling. Household names like Kacey Musgraves and Florida Georgia Line got their start here.  

Hemingway Days (July 17-20, 2024) honors the giant legacy of author Ernest Hemingway by doing something he did best: celebrating. The festival includes presentations by Hemingway scholars, appearances by Hemighway family members, and an awesome look-a-like contest where hundreds of white-bearded, swarthy men channel their inner “Papa.”

Fantasy Fest (October 18-27, 2024), which started as a costumed parade down Duval Street, has grown into 10 days of parades, parties, street fairs, and fantastical balls. Most of these activities are not for kids. Adults might have fun at the “naughty” bike rides, pajama parties, and burlesque shows across the city. So, if you are visiting Key West with kids, avoid that week! 

Key West Has Many Famous Buildings

Key West is filled with buildings with an intriguing history. Aside from the more popular places like the Hemingway House and the Truman Little White House, several other famous buildings exist.  

The Audubon Hosue and Tropical Gardens showcases works from the ornithologist John James Audobon. Audubon drew 18 new birds after having visited Key West. You can explore the house and its 1-acre surrounding gardens.  

The Basilica of St. Mary Star of the Sea is Florida’s second oldest Catholic parish, founded in 1846. Pope Benedict XVI raised the church to a minor basilica in 2012. You can enter the basilica and take a self-guided tour.

The Mel Fisher Maritime Museum contains an extensive collection of treasures and artifacts from 17th-century shipwrecks. The museum highlights the discoveries of treasure seeker Mel Fisher and his contributions to maritime archeology. Here, you can see Spanish gold coins, learn about the real pirates of the Caribbean, and explore the science of shipwrecks. Tickets are required. This is one of my top recommendations for families who want to learn more about the pirate history of Key West.

Key West Is Known As The Conch Republic  

Did you know  Key West  once seceded from the US and became its own country?  

In 1982, out of frustration over a border checkpoint that stopped most traffic into and out of the keys, Key West sarcastically notified the Federal government they were seceding from the Union. They gave their new country the name “Conch Republic.” 

This name has become a unifying moniker for the people of the Keys and a rallying cry for citizens who value freedom and independence. You’ll see the name all over. Even the Key West high school got the fever, naming their mascot the “Fighting Conch.”  

I laughed when I saw the Conch Republic’s official flag, which bears the motto “We Succeeded Where Others Failed.”

Key West Is Home To The Oldest Bar in Florida, or Is It?

Caption Tony’s is an iconic bar located just a block off Duval Street and was actually the original home of Sloppy Joe’s Bar. The sign out front says it’s the oldest bar in Florida. However, other sources say that the The Palace Saloon on Amelia Island is the oldest bar in Florida. I will have to pop in and ask them about it when I visit next month!

Did you know that Jimmy Buffett played Captain Tony’s in the early 1970s?

Key West Is A Fisherman’s Paradise

Anglers in the Keys have caught some of the largest fish on record in Florida. These include a 240-pound Yellowfin Tuna, a 243-pound Tarpon, a 612-pound Swordfish, and a 686-pound Great White Shark.  

Key West has a legendary reputation for fishing. Initially made famous by the stories of Hemingway, the coral reefs and deep blue waters of the Florida Straits are well-known for their massive catches.  

Fishing here is diverse, and many different fish are regularly biting. Tarpons are heavyweight champions and can top 200 pounds. Bonefish are called “Grey Ghosts”; they are smaller but harder to find. Snapper and Grouper can be caught year-round and are sought after for their great taste. They like patch reefs, wrecks, and bridges and can even be caught from shore. If you want to go farther from shore, Blackfin Tuna are wonderful to eat and very plentiful in the spring. Sailfish, Swordfish, and Marlin are the kings of the sea and will give you the fight of your life.  

These majestic giants drew Hemingway here and continue to thrill sport fishers with their strength and size. The warm waters off the coast bring in smaller Blacktip and Bonnethead sharks. Or you can pit yourself against apex predators like the giant Bull, Tiger, and Hammerhead sharks. 

Key West Was Once The Cigar Capital Of The US

Many people don’t know Key West was the original epicenter of the Cuban cigar industry in America.  

The first cigar factory started here in 1831, and by 1890, there were at least 80 factories in Key West. The factories were tightly connected to Cuba and would import Cuban tobacco leaves to be hand-rolled by Cuban emigres in Key West factories. The legendary Arturo Fuente began rolling here in 1912.  

After hurricanes hit Key West, destroying some factories, and local unrest around labor unionization, most factories moved to Ybor City in Tampa. Several small factories still operate in Key West, like the Key West Cigar Factory, Rodriguez Cigars, and the Island Cigar Factory. 

Jimmy Buffett Got His Start In Key West

The iconic singer and songwriter Jimmy Buffett moved to Key West in 1972. After having no success in the Nashville record business, he decided to take a trip with a friend to the Keys for some needed relaxation.  

He ended up living in Key West for seven years, working various odd jobs and singing in the local dives and honk-tonks. The island ambiance of the Keys inspired his casual style and tropical-themed lyrics. His hugely popular songs like Margaritaville became synonymous with Key West, and enjoying the salt and sea lifestyle became a popular pastime for fans worldwide.  

I read some amazing stories about Jimmy’s time in the 1970s in  Key West . He became part of a “Rat Pack” of close friends, many of whom were aspiring authors and poets, all following the spiritual footsteps of Hemingway. Stories of epic week-long deep sea fishing trips, hard-partying, and great friendship make this era of his life reminiscent of the “Lost Generation” of Paris ex-pats in the 1920s. 

A book I love that focuses on Jimmy and his rat pack in the 1970s is titled  Mile Marker Zero: The Moveable Feast of Key West .  And if you haven’t read  A Pirate Looks At Fifty , you must!

The Rum Runner Drink Was Invented Near Key West

Legend has it that the famous Rum Runner cocktail was invented in 1972 at the Holiday Tiki bar in Islamorada, near Key West.  

In one story, bartender John Ebert was challenged by the Holiday Tiki Bar owner to use up a lot of unused liquor that hadn’t been drunk (called “dead stock”). John mixed the ingredients in a new way to make the first Rum Runner.  

In another version of the story, John was looking for a job, and the owner of the Tiki Bar asked him as part of the interview to make a delicious drink with lesser-known ingredients.  

Either way, we now have the tasty Rum Runner – a sweet libation that has slaked the thirst of many a beach bum and tropical reveler around the globe.

Enjoy The History Of Key West On Your Next Trip

Key West history is filled with fascinating stories of larger-than-life personalities, rising and falling fortunes, boom and bust industries, and enduring people committed to life by the sea. Their stories are diverse, but they are all driven by fierce independence and a yearning for freedom away from society.  The fun thing about the history of  Key West  is that there are always new tales to listen to on every visit!

Key West is one of my favorite places to visit because of its charming eccentricity and its desire to be true to itself. It’s a fantastic place to relax, try new things, and enjoy the “Salt Life.” When planning your trip to the Conch Republic, be sure to set aside time to see some of the historical places. Catch the setting sun and sip a Rum Runner while you marvel at all this city offers.

And if you are looking for things to do in Key West, I have got you covered with several great Key West travel blog posts! 

• 18+ Things For Families to Do in Key West
• Riding the Iconic Conch Train Tour in Key West
• All About the 6-toed Hemingway House Cats
• My Momcation at the Marker Key West
• Visiting the Truman Little White House
• Snorkeling & Sunset Tours with Sebago Watersports
• The Key West Hop-On Hop-Off Old Town Trolley Tour