Top Key West Historical Tours - page 2

Key West Historic Seaport Food & Walking Tour

4.9

(662)

3 hoursFree Cancellation

from $93

Use professional paranormal investigation equipment as seen on TV, film, and in the field

Are you brave enough to lock eyes with the world's most haunted object… in the dark? Don't get stuck on a crowded trolly, step behind the velvet rope with us and investigate Key West's greatest mysteries and darkest legends. Located within a museum named one of America’s 10 Most Haunted Destinations, join us at the historic Fort East Martello for an eerie evening centered around the chilling legend of Robert the Doll. This isn't just a story—it's an encounter. Your night begins with a 30-minute guided ghost tour through the shadows of the Civil War-era citadel, where you’ll learn the dark history of the site. Then, settle in for a 30-minute seated experience directly with Robert. We will separate the terrifying facts from the folklore and discuss the latest activity surrounding the doll.

Robert the Doll After Dark

134

1 hourFree Cancellation

from $45

Discover the spooky side to one of the country's most haunted cities on a 90-minute walking tour. Listen to hair-raising local legends as you follow your guide down the hidden alley's of Key West. See where Robert the Doll lived, learn about Count Von Cosel, and keep your eyes peeled for the ghost at La Concha. Learn how to attract spirit activity with dowsing rods and how to capture it with your camera.

Key West Ghost and Mysteries Guided Tour

4.5

(1,102)

Key West - Museum Culture Pass

from $33

4.0

(20)

4 to 5 hoursFree Cancellation

from $45

Go sightseeing in the Florida Keys at your own pace with a private self-guided audio tour. Choose a northbound or southbound itinerary and learn about local landmarks, history, and more during the drive. Set out on a road trip through the Florida Keys and learn about highlights such as Seven Mile Bridge and John Pennekamp State Park along the way. Tour offline using GPS, with no cell service needed.

Self-Guided Audio Tour in Florida Keys

4.7

(91)

from $17

Key West Haunted Pub Crawl Walking Tour

Florida Key West Self-Guided Driving Tour (7 Mile Bridge)

from $35

4.5

(73)

2 to 3 hoursFree Cancellation

from $17

Per group

4.3

(135)

The Ghosts of Key West Walking Tour

Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk. This self-guided adventure immerses you in the rich tapestry of island life where writers like Ernest Hemingway and Tennessee Williams found their muse. Navigate through charming streets, lively bars, and historic neighborhoods that showcase the unique blend of Caribbean, Cuban, and Conch cultures. As you stroll at your own pace, engaging audio narratives reveal tales of resilience, creativity, and community that define this iconic island. Discover the essence of Key West, where every corner invites you to pause, reflect, and connect with its storied past.

from $30

Step into the free-spirited heart of the Florida Keys with the Key West Conch and Hemingway Walk, a self-guided journey through an island shaped by writers, wreckers, and working-class dreamers.

Key West Conch and Hemingway Self-Guided Walk

2 hours to 2 hours 30 minutesFree Cancellation

from $10

Naval history buffs and aspiring pirates alike are guaranteed to have a whale of a time at the Mel Fisher Maritime Museum. Your admission also includes an audio guide, which offers in depth commentary on the museum’s many artifacts. Highlights include the Spanish Treasure Galleons galleries, Slave Ship and Key West African Cemetery exhibits, and relics from the Henrietta Marie. You can even tour the museum's laboratory and see conservation firsthand.

Skip the Line: Mel Fisher Maritime Museum Admission Ticket and Audio Tour

4.2

(30)

1 to 4 hoursFree Cancellation

from $20

3.8

(104)

Key West Shipwreck Treasure Museum Admission

Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to? Stop in his favorite bars for a drink? You are in luck. Our tour will begin at the Florida Keys Historical Military Memorial in Mallory Square and wind our way along storied streets and the favorite haunts of Hemingway himself, until we reach the iconic Hemingway Home and Museum and the towering Key West Lighthouse. You’ll see his bust, his favorite bar, the spot he first lived, where he ate and lived. And you’ll also hear the story of Key West along the way. Go at your own pace, stop anytime for a drink, and continue when you want. The tour never expires.

from $19

Hemingway's Key West Self Guided outdoor Walking Audio Tour

4.0

(2)

1 hour to 1 hour 30 minutesFree Cancellation

from $8

Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.

Original Key West Pub Crawl: The Best Bars with Free T-Shirt

4.6

(362)

2 hours 30 minutesFree Cancellation

from $43

The USCGC INGHAM was the longest continually serving, most decorated ship in Coast Guard History. Serving in active duty from 1936 to 1988. Only remaining American ship afloat to have fought in the Battle of the Atlantic. Command ship for several Philippines landings including General Douglas MacArthur's return to Corrigedor, he was aboard during this action. First allied vessel into Chinese waters at wars end. Two Presidential Unit Citations for support missions in Viet Nam. Also part of the Mariel Boatlift, when tens of thousands of Cuban refugees left their island home seeking refuge in the U.S. Now a National Historic Landmark and Coast Guard National Memorial to Guardsmen that have lost their lives in World War Two and Viet Nam. The Ingham also offers one of the best sunset views in Key West.

Key West USCGC INGHAM Maritime Museum

4.9

(80)

20 minutes to 2 hoursFree Cancellation

from $23

Southernmost Point in the Continental USA!

4.9

(22)

PRIVATE Welcome to Key West Walking Tour

1 hour 30 minutes to 3 hoursFree Cancellation

from $138

This self-guided audio tour takes you through the Key West Cemetery, a unique graveyard filled with characters that shaped the island's bohemian past. Join Frank Everhart, a nearly 30-year Key West resident, on a walking tour where you'll uncover the secrets of legendary figures, millionaires, and families. As you stroll among crumbling graves, spot descendants of Cuban cockfighting roosters and sun-bleached iguanas. Hear stories of the 1846 hurricane, the Freemasons, and the USS Maine Memorial, whose victims' deaths sparked the Spanish-American War. The 75-minute tour starts at the main entrance, passing through the Jewish B'Nai Zion Cemetery, where you'll learn to decipher gravestone symbols.

A Self Guided Key West Cemetery Tour

4.0

(3)

1 hour 15 minutes to 1 hour 30 minutesFree Cancellation

from $30

Explore America's most haunted firehouse on an after-hours investigation inside one of Florida's oldest remaining firehouses.

America's Most Haunted Firehouse

(8)

Journey through Key West's history on this self-guided adventure featuring swashbuckling pirate legends and maritime mysteries. Your smartphone transforms a regular walk into an epic quest, with historical puzzles, fascinating stories, and clever challenges at every stop. Each location brings history to life — from ancient landmarks to hidden historical details you'd walk right past without the app. Solve challenges to unlock the next chapter of Key West's story. This 1–2 hour private adventure runs 24/7. No guide needed — just your smartphone and a sense of curiosity. Available in 5+ languages.

from $95

Key West Pirate Adventure: Self-Guided Walking Tour

from $5

Key West’s Old Town is a wonderfully walkable area that’s best enjoyed at a slow and steady pace. Take advantage of free time under the sun while learning about the history of the island during this self-guided audio tour of Old Town. A tour guide narrates this journey up and down the streets, having you stop at attractions like the Little White House and the Lighthouse. You’ll end your walk at Mile 0: the Southernmost Point of the Continental US.

Key West’s Old Town Treasures: A Self-Guided Audio Tour

4.3

(29)

1 hour 30 minutes to 2 hoursFree Cancellation

from $15

Tours will begin at the corridor of the Southernmost District near the Key West Lighthouse and the home of the infamous author Ernest Hemingway. We will proceed through the Southernmost District and continue onto the neighborhood where the historic "Bahama Village" remains. Your experience will be provided by a fifth generation native of Key West and will include the history, folklore and architecture of traditional Key West.

Bahama Village Walking Tour

1 to 2 hoursFree Cancellation

from $30

Old City Hall, Key West, Former Firehouse and Police Station

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and shocking history exposed where it happened. More thrilling than a ghost tour and more revealing than a history tour, Key West’s underworld comes alive, Key West-style. Be the next eyewitness. We're bringing crime to the streets!

iWitness Key West True Crime Walking Tour

(15)

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s Episcopal Church, where we will share stories of its haunted past and the intriguing legend of Robert the Doll. Next, visit The Artist House, where we will delve into the bizarre true story of Carl and Elena, followed by Dean-Lopez Funeral Home and Crowne Plaza Key West-La Concha, which have a dark and chilling past. At Marrero’s Guest Mansion, explore the eerie story of Enriquetta and other ghostly legends associated with this haunted yet historic mansion. Moving on to 322 Duval St, uncover the mysteries of Captain Watlington’s Haunted House and share bone-chilling stories of the haunted past and present of Key West. Our journey concludes at the Audubon House & Tropical Gardens and the infamous Capt Tony’s Saloon, discovering their dark histories and encounters with the paranormal.

from $45

Likely to Sell Out

Dark Corners of Key West Private Walking Tour

(1)

from $393

Key West is a wonderfully walkable island that deserves just as much exploration under the moonlight as it does under the sun. Avoid crowded group tours with this private self-guided ghost tour. Using your smartphone, you’ll explore Key West’s allegedly haunted sites and hear their grizzly histories. Go at your own pace, taking breaks or visiting other Key West attractions as you continue your adventure.

Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader

4.2

(9)

40 to 55 minutesFree Cancellation

from $10

See this beautiful haunted mansion & hear the history of it's creepy past residents

PRIVATE Key West Haunted History Walking Tour

(10)

1 hour 30 minutes to 2 hoursFree Cancellation

from $138

The Hemingway Experience in Key West

1 2 3

Top Attractions in Key West

1 / 2

Attractions

What are people saying about Key West

Dawn_T, Apr 2026

Hemingway Experience

This is a great way to see several things in a short period of time. My only recommendation would be to allow extra time to go back to the Hemmingway house and thoroughly enjoy reading all the history. Kyle did a great job showing us all the hotspots!

Jimmy Buffett Tour

Dennis_N, Apr 2026

It's well worth the...

It's well worth the money. Our guide JP was very knowledgeable and friendly. He paced the walk to our group...so e of us were a but older. The key Lime Pie was outstanding and the water was very refreshing. The margaritas at the end was the perfect ending to a fun and informative tour.

Harry S Truman Little White House Admission

Jennie_O, Apr 2026

Be prepared to be on your feet for 90 minutes.

You will stand for at least 20 minutes in the dining room while listening to the presentation. The entire tour and presentation is very informative and professional and takes maybe 70 minutes, all while standing. There are a few chairs offered in the last room. The stairs are narrow and some declined climbing up to the second floor. I enjoyed learning about The President who lived in the house. I would do it again.

Guided Bike Tour of Old Town Key West

Dana_G, Apr 2026

LOVED IT! Can’t recommend this enough!!

This was everything we hoped it would be and more! It was a great ride through old town key west, with running history tutorials. Our guide Ted was very knowledgeable, funny, engaging, and really brought the history to life. 10/10 would do this again and again. HIGHLY RECOMMEND! Also, the cold key lime hi at the end of the bike tour was the best ending!!

Key West Historic Seaport Food & Walking Tour

Joleen_B, Feb 2026

Interesting with great food!

Our guide had so many interesting stories to share, we had great food especially enjoying the seafood market shrimp and Garbo’s tacos! Rose answered all of our questions and was sure to include everyone in the group. The size of 12 people was perfect for our walking and eating event.

Key Lime Pie Walking Tour of Key West Historic Seaport

Pamela_S, Feb 2026

The Perfect Slice of Key West

This walking tour was the perfect slice of Key West—sweet, relaxed, and full of local flavor. From the very first stop, it was clear this wasn’t just about eating key lime pie (though wow, did we eat some excellent pie), but about understanding the history, rivalries, and passion behind it. Kim was knowledgeable, funny, and clearly loved Key West and its food scene. We visited several spots each with a distinct take on key lime pie—from classic and tart to creamy and frozen. Every stop felt thoughtfully chosen, and the pacing of the walk was easy and enjoyable. Between bites, we learned about the origins of key lime pie and how this humble dessert became such a defining symbol of the Keys. It felt like a delicious mix of food tour, history lesson, and friendly stroll. If you’re visiting Key West and want an experience that’s uniquely local, not overly touristy, and genuinely fun, this tour is an absolute must. Come hungry and be prepared to leave with a strong opinion about what makes the best key lime pie!

Key West Conch Tour Train

Melanie_B, Jan 2026

Fun way to learn about Key West!

Our guide, Kenny, really made this train ride special. He’s a Key West native and has the most interesting stories! This is a fun way to learn about Key West and take a break and enjoy the ride around the area. Would definitely recommend if you’re interested in the history of Key West or just wanted to get the lay of the land and rest your feet from all the walking! Fun activity!!

Key West’s Old Town Treasures: A Self-Guided Audio Tour

April_L, Sep 2025

Informative

It started raining right when we started the self guided tour. Thankfully we brought ponchos. We just kept going and the weather did not affect us learning about Key West. My husband was thankful for the experience that didn’t leave us stranded in a shop or restaurant waiting for the rain to stop. We added a few stops on the way. We didn’t tour inside any of the stops but still enjoyed it.

Florida Key West Self-Guided Driving Tour (7 Mile Bridge)

Patricia_C, Aug 2025

Best Way to Learn About the Keys While Traveling the Route 1

We enjoyed the historical information detailing how the Keys progressed from a shipping/wrecker industry to a military stronghold to a popular travel destination made possible first by the railroad and then by Route 1, Key West Airport and cruise ships. Interesting landmarks were highlighted along with great recommendations for places to stop for lunch, local arts & crafts, a beach break, or longer stops to see local marine life. Of course, no trip along the Keys would be complete without learning about the famous and/or quirky characters who made the Keys their home. Very entertaining storytelling!

Key West Historic Bahama Village & Hemingway Heritage

Frantzline_G, May 2025

thanks AJ!

great experience. We learned a lot from this tour, especially since it put a lot of things in context when exploring key west. We took a walk through bahama village before the tour and didn't even know about all the history it was hiding. There's a lot of reasons why Key west is the way it is (housing, street names, restaurants) and you learn all about it in the tour.