Top Key West Historical Tours

Key West Hop-On Hop-Off Trolley Tour

from $45

4.4

(1,658)

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at (6) locations, helping tell Hemingway’s story in Key West & Cuba. Each ticket includes guided entrance into his famed Key West home. Then eat, drink, and explore the island on foot through “Papa’s eyes”, feasting on Cuban cuisine (& 3 boozy beverages) while your knowledgeable local guide impresses with interesting stories & amazing fun facts. The adventure takes you behind the scenes of a 3rd generation family run cigar rolling factory, and into the newly remodeled Social Club at Hemingway Rum Co. for his favorite drink made with his family company’s premium rum. Then finish with a slice of our famous key lime pie! After the tour, you’ll receive a collection of exclusive recipes, recommendations on restaurants, attractions, entertainment, and cultural offerings.

from $56

Likely to Sell Out

The Hemingway Experience in Key West

4.8

(49)

4 hoursFree Cancellation

from $185

Pedal through the charming streets of Old Town Key West on a guided bike tour, perfect for first-timers exploring the island. Along the way, you’ll uncover its rich history and stop at iconic spots like Mallory Square, Mile Marker Zero, and the Southernmost Point Buoy. With morning and afternoon tour options, it’s easy to soak in panoramic ocean views and experience Key West at your own pace.

Guided Bike Tour of Old Town Key West

4.9

(2,697)

Discover an important part of Florida’s history with admission to the Harry S. Truman Little White House. This former naval base compound is now a treasured museum, open to educating the public about its past and present. See where President Truman retreated for rest and relaxation during his term in office. Learn about the notable people who visited, including Thomas Edison and Dwight D. Eisenhower. And listen to the stories told by those historians who not only know what happened here, but when and why.

from $59

Harry S Truman Little White House Admission

(471)

1 to 2 hoursFree Cancellation

from $26

Explore the vibrant sights of Key West with the Old Town Trolley, Aquarium, and Shipwreck Museum package. This tour offers unlimited hop-on, hop-off access to 13 convenient trolley stops, allowing you to explore highlights like the renowned Key West Aquarium and the fascinating Shipwreck Treasure Museum at your own pace. Experience engaging guided tours, marvel at daily turtle feedings, and discover the rich history of shipwrecking that shaped this unique island. Perfect for families and history enthusiasts alike, this package includes free admission to the Sails to Rails Museum and exciting discounts. - Unlimited access to the trolley service for a day - Visit the Key West Aquarium with daily interactive experiences - Explore the Shipwreck Treasure Museum and learn about maritime history - Enjoy free admission to the Sails to Rails Museum and special discounts

Key West Attractions Pass with Trolley Tour

3340

Discover some of Key West’s deepest, darkest secrets on a ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of what is said to be one of the most haunted cities in the US. Travel down the narrow, dark streets of the Old Town at night. The wooden houses still bear the secrets of their former inhabitants. This tour is narrated by an actor playing a gravedigger.

from $93

Key West Ghosts and Gravestones Trolley Tour

4.3

(1,299)

1 hourFree Cancellation

from $40

Key Lime Pie tasting at a local favorite restaurant!

4.9

(48)

Key Lime Pie Walking Tour of Key West Historic Seaport

from $70

History And Culture Walking Tour in Key West

Key West Historic Bahama Village & Hemingway Heritage

(254)

Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and delicious key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.

from $47

Southernmost Food & Cultural Walking Tour by Key West Food Tours

4.9

(1,846)

3 hoursFree Cancellation

from $90

Capt. Tony's Saloon- The Original Sloppy Joe's

Hemingway Food and Walking Tour

(110)

from $99

4.6

(304)

Jimmy Buffett Tour

Key West Historic Schooner When And If Sunset Cruise

from $79

4.8

(134)

from $109

Southernmost Key West History and Culture Small-Group Walking Tour

(132)

1 hour 45 minutesFree Cancellation

from $40

Likely to Sell Out

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Shark and Wildlife Viewing Adventure in Key West

(3,183)

Key West Shipwreck Treasure Museum Admission

from $99

3.8

(103)

Don't let the trolley take you for a ride. We're the only ghost tour in Key West where you'll walk the dark halls of historic Fort East Martello with authentic ghost-hunting equipment and meet Key West's infamous haunted doll, Robert. USA Today named us one of America's 10 Most Haunted Destinations, and Thrillist calls us "The Creepiest Place in Florida." See for yourself, but be warned: we actively engage spirits, so our hunts are not for everyone. We're family-owned by real Key West locals, and our Google satisfaction rating is 4.9. Our owners opened the first ghost tours on the island and wrote Ghosts of Key West, Haunted Key West, and the biography of Robert the Doll. Book VIP here for the two-hour ghost-hunting adventure, which includes an additional hour hunting ghosts on your own after the guided tour. (Book General Admission tickets on our site for the one-hour guided tour only). There are dozens of ghost tours in Key West. See why people are dying to get into ours.

from $19

VIP Robert the Doll After Dark

(164)

Key West's most mind-blowing sky watch! Search for UFOs with your military-grade night vision scope as we blow your mind with tales of UFOs, UAPs, alien encounters, and the hidden history of UFOs in Key West. Small groups, local guides, little-known history, and oceanfront viewing sites make this a unique, unusual, unforgettable experience. Your $5000 night vision scope will change how you see the night sky forever. This experience is dependent on suitable viewing conditions. If we cancel you will have the option to reschedule or be refunded.

from $99

Enjoy our star-filled skies and histories from a colorful local guide

1 hour 15 minutesFree Cancellation

134

Key West UFO Tour

from $74

4.5

(73)

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

2 to 3 hoursFree Cancellation

from $17

Per group

Visit the only Breadfruit Grove in Continental United States! While here, discover the rich history of Grimal Grove and its legendary founder, Adolf Grimal, on a 75–90-minute tropical fruit hunting tour. This engaging experience takes you through the grove where you'll learn about its 70+ year journey of restoration and resilience. Depending on the season, guests may even have the chance to pick ripe fruits directly from the trees. The tour includes a scenic walking exploration, followed by a delightful tasting session in an outdoor tasting room featuring prepared exotic fruits. - 75–90-minute tour revealing the history of Grimal Grove - Guided walking tour with opportunities to pick fruit (seasonal) - Outdoor tasting experience with a variety of exotic fruits - Learn about the 70+ years of restoration and resilience at the grove

Tropical Fruit Hunting Tour at Grimal Grove

(10)

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.

from $38

Self-Guided Audio Tour in Florida Keys

(91)

1 day

from $17

Per group

Explore beautiful coastlines, wild history, and fascinating wildlife with this self-guided walking tour of Key West. Get to know famed author Ernest Hemingway and the island’s influence on his work. Hear stories of pirates, shipwrecks, and disasters and marvel at lush tropical gardens and coastline. Then stroll along Duval Street, the bustling heart of Key West, and savor the rich culture of this one-of-a-kind island. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Florida Key West Self-Guided Walking Audio Tour

(25)

2 to 3 hoursFree Cancellation

from $10

Relive the life of one of history’s most famous treasure hunters along with a wealth of exhibits on shipwreck archaeology with this admission to the Mel Fisher Maritime Museum. This Key West institution showcases a variety of treasures, both cultural and monetary, recovered from the treasure and slave ships that once plied the waters near the Florida coast. Check out the thought-provoking Slave Ship and Key West African Cemetery exhibits, then gaze in wonder at the magnificent gold, silver and jewels of the Spanish Treasure Galleons galleries.

Mel Fisher Maritime Museum Admission Ticket

4.2

(131)

1 to 2 hoursFree Cancellation

from $18

4.3

(135)

The Ghosts of Key West Walking Tour

The Hemingway Experience in Key West

from $30

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Top Attractions in Key West

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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

Catherine_B, Apr 2026

Do this tour!

This tour is a fantastic way to see Key West, and hear its story, get recommendations, and indulge in a free slice of key lime pie! James was our guide, and he was amazing! Such an interesting, knowledgeable, and likable person… we really, really enjoyed it!

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 Historic Bahama Village & Hemingway Heritage

Barbara_S, Jan 2026

AJ was knowledgeable...

AJ was knowledgeable about the early Cuban and Bahaman cultures that contributed to the historic neighborhoods. He provided historic photos on a laptop computer as we walked. His knowledge of architecture helped understand the community growth. We do recommend this as a cultural experience.

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!