Key West
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A Self Guided Key West Cemetery Tour
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.
4.0(3)
1h 15m - 1h 30m
Key West
- Free cancellation
- Private tour
From
$30
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Viator
Hemingway's Key West Self Guided outdoor Walking Audio Tour
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.
4.0(2)
1 Hour - 1h 30m
Key West
- Free cancellation
- Private tour
From
$8
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Viator
An Audio Guide of Key West’s Journey From Village to Micro State
Key West is famous as mainland America’s Caribbean resort town. Here, time slows down as the island vibes take over. But, as you’ll soon find out on this walking tour, there’s more to this island than umbrella drinks and warm breezes. On this tour, travel writer and tour guide Gregg Squeglia will share stories of some of the island’s more famous residents and some lesser-known tales that have given Key West its unique place in American culture and history. He'll tell you about Key West’s incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships along the Great Florida Reef to the hilarious creation of the ‘Conch Republic’. You’ll also find out how, soon after its creation, this micro-state declared war on the United States for a full minute. On this self-paced tour, you’ll also visit the island’s major landmarks and lesser-known treasures.
4.0(1)
2 Hours - 2h 30m
Key West
- Free cancellation
- Private tour
From
$12
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Viator
Key West Scavenger Hunt Adventure Mobile Experience
Turn Key West into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour city walking tour. Guided from any smart phone, teams make their way among well known and overlooked gems of the city, solving clues and completing challenges while learning local history.
3.9(8)
3 Hours
Key West
- Free cancellation
From
$49
No similar experiences found
Viator
Key West Ghost Tours: Southernmost Shadows and Ghosts
Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate storytellers, you’ll wander through historic Old Town, where every corner hides a ghostly tale. As you walk under the moonlight, prepare to be captivated by chilling stories of spirits from Key West’s history. This tour visits nine to thirteen of the most haunted spots in Key West, where you’ll stand on the very ground where ghostly encounters have happened. While the tour doesn’t enter private buildings, just being near these haunted places is thrilling. Picture yourself standing by the historic Curry Mansion or the mysterious Casa Antigua, hearing the true, spine-tingling tales that have been told for generations. Covering a mile of haunted history, this tour is perfect for history lovers, thrill-seekers, and anyone curious about the supernatural. Southernmost Ghosts promises a night of unforgettable stories and lasting chills.
3.8(21)
1 Hour
Key West
- Free cancellation
From
$26
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Viator
Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!
We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West! Our seasoned local guide will dive into the history of Old Fisherman’s Wharf & how it has transformed into Yacht Harbor! Learn about the historic wrecking and rum running days of old Key West! Sit at the bar Mel Fisher did while his treasure sat out front, on display, in the trunk of his car! Transition into the sunset where you’ll visit the area where locals have their annual celebration for the succession of our Conch Republic from the United States! Open your ears to live music and island vibes as you cocktail into World Famous Mallory Square’s Sunset Celebration!
3.7(18)
2 Hours - 3 Hours
Key West
- Free cancellation
From
$139
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Viator
Marathon Offshore Fishing Charter
Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and fantastic food. View the beautiful scenery, while experiencing the thrill of a chance to catch species such as Sailfish, Wahoo, Mahi Mahi, Tuna, Snapper, Grouper, King Mackerel, and Shark. Your tour is guided by a licensed Captain in a 30” open fishing style boat with t-top for shade. All the fishing rods and reels, right and left-handed and all the tackle you need, as well as all other necessities including safety equipment. Travelers that have enjoyed our fishing charters also have enjoyed The Turtle Hospital, a tour down Seven Mile Bridge or a beautiful sunset at Sombrero Beach.
3.7(3)
4 Hours
Key West
- Free cancellation
- Private tour
From
$1,500
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Viator
Key West Island Jetski Tour: Double Passenger Jetski
27 Miles and 90 Minutes of pure exhilarating watersports bliss. Your Key West Island Jet-ski Tour starts in the shallow cove, The Ibis Bay Resort dock area. From the Gulf of Mexico to the Atlantic Ocean.....and back to the Gulf of Mexico. From sea to Ocean and back again. After your exhilarating 90-minute adventure, many guests celebrate their experience with a drink and the freshest seafood at the Stoned Crab Restaurant.
3.1(11)
1h 30m
Key West
- Free cancellation
From
$180
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Viator
Southernmost Key West Historical Tour in Small Group
Travel The Keys is a guided tour and concierge company based in Key West, Florida. We offer unique historical tours in Key West, presented by a 5th generation local. Our tours present a collection of lesser known historical events and explore the cultural legacies of the Southernmost District and surrounding areas of Key West.
3.0(2)
1 Minutes - 1h 30m
Key West
- Free cancellation
From
$30
No similar experiences found
Viator
Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Return at 12:00pm and have 4 hours of free time before you come join us for an incredible Key West 2 hour Catamaran Sunset happy hour tropical dinner cruise with margaritas, rum runners, wine, beer and live music.
3.0(1)
5 Hours
Key West
- Free cancellation
From
$160
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Viator
Key West Culinary and Catamaran Reef Tour Experience
Explore the vibrant waters of Key West on this 4-hour dolphin watch and snorkeling tour aboard a luxurious catamaran. Encounter playful dolphins in their natural habitat and dive into the colorful coral reefs, guided by experienced crew. After snorkeling, indulge in a delicious Taste of Key West menu featuring local specialties like conch fritters and shrimp ceviche, complemented by an open bar of refreshing cocktails. With professional instruction and a maximum group size for personalized service, this tour promises a unique blend of marine exploration and culinary excellence. - 4-hour tour featuring dolphin watching and guided snorkeling - Chef-prepared menu with local favorites and an open bar - Professional crew with extensive knowledge of local ecosystems - Maximum group size ensures personalized attention and comfort
1.0(1)
4 Hours
Key West
- Free cancellation
- New
- Likely to sell out
From
$79
No similar experiences found
Viator
Key West Pirate Adventure: Self-Guided Walking Tour
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.
1h 30m
Key West
- Free cancellation
- Private tour
From
$5
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Viator
Rum Cocktail Masterclass
Step into the world of rum and discover the art of crafting exquisite cocktails at a hands-on masterclass. Whether you're a novice or a seasoned mixologist, this class offers something for everyone. Guided by expert bartenders, you'll uncover the secrets behind both classic and contemporary rum cocktails. Dive into a variety of rum styles, including two local treasures: First Legal Rum, celebrated for its smooth and rich flavor, and Pilar Dark Rum, known for its deep, complex taste with hints of caramel and spices . Master essential techniques while enjoying a fun time with friends or a unique date experience. Imagine the joy of shaking, stirring, and sipping your own creations as you toast to new skills and delicious drinks!
1 Hour
Key West
- Free cancellation
From
$81
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Viator
Dry Tortugas National Park Self-Guided Audio Tour
Explore an island paradise 70 miles west of Key West. Visit Fort Jefferson, a massive 19th-century coastal fort, and walk its brick walls while hearing stories about soldiers, prisoners, and shipwrecks. The tour even works on the ferry to this remote national park. Snorkel in clear blue water filled with coral, tropical fish, and sea turtles. Relax on sandy beaches and look for seabirds that nest only here. Stroll through the fort’s archways, climb to the top for ocean views, and learn how the fort defended the Gulf of Mexico. You choose what to do first—swim, explore the fort, or enjoy the beach. The tour works without internet, gives GPS directions for walking the site, and offers local tips you can keep forever. Download the tour, take the ferry or seaplane, and explore this unique national park at your own pace—where history, nature, and crystal-clear waters meet. Download the Shaka Guide app to access the purchased tours
7 Hours - 8 Hours
Key West
- Free cancellation
- Private tour
- New
From
$13
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Viator
Key West Conch and Hemingway Self-Guided Walk
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.
2 Hours - 2h 30m
Key West
- Free cancellation
- Private tour
- New
From
$10
No similar experiences found
Viator
A Snorkel Tour with a Twist of History, Marathon, Florida Keys
Experience premier snorkeling in the Florida Keys aboard the Island Pearl, a 50-foot classic vessel with modern comforts and a colorful past as the liberty boat for the USS Roosevelt. Set off on a scenic excursion past Marathon’s iconic landmarks while we share fascinating stories of the Keys’ historic past. Then, explore vibrant reefs teeming with marine life, or simply relax on the water and take in the views. Even if you’re less adventurous or prefer to stay dry, there’s plenty to enjoy—this is a tour that truly lets everyone in your group experience the magic of the Keys. This unique adventure is quickly becoming a Florida Keys tradition for visitors who want history, scenery, and unforgettable snorkeling.
3 Hours
Key West
- Free cancellation
From
$70
No similar experiences found
Viator
Dry Tortugas Boat Charter from Key West
Explore the stunning Dry Tortugas National Park with a private boat charter tailored just for you. Departing from Key West, enjoy a full-day offshore adventure that includes visiting historic Fort Jefferson and snorkeling in crystal-clear waters. This exclusive experience allows you to set your own itinerary, ensuring a flexible and customized journey without the crowds. Your adventure is aboard a premium charter vessel, captained by experienced locals familiar with the area, making your visit both enjoyable and memorable. - Private charters provide a customized experience for your group - Full-day exploration of the Dry Tortugas National Park - Snorkeling opportunities at beautiful locations - Flexible itinerary means you choose the pace and activities
8 Hours
Key West
- Free cancellation
- Private tour
- New
From
$1,800
No similar experiences found
Viator
Dolphin Watch and Snorkel Tour in Key West
Explore the vibrant waters of Key West on this exciting Dolphin Watch & Snorkel Tour. Enjoy a family-friendly adventure as you snorkel in the beautiful backcountry waters, home to an array of marine life including tropical fish, sea turtles, and more. Spot dolphins in their natural habitat and soak in the stunning surroundings aboard a spacious catamaran. With expert guidance and all snorkeling gear provided, it's perfect for both beginners and experienced snorkelers. Relax afterwards with snacks and refreshing drinks as you share stories of the day’s adventures. - Duration of the tour is 3.5 hours, offering plenty of time for exploration. - All snorkeling equipment is included, with expert instruction available. - Enjoy complimentary snacks and drinks, including beer and soft drinks. - Limited to 36 guests for a comfortable and spacious experience.
4 Hours
Key West
- Free cancellation
- New
From
$90
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Viator
Private Southernmost Key West History and Culture Walking Tour
Join us for the best walking tour in Key West! You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA! Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States. The private tour is the best way to explore Key West and have fun with your own group of friends or family! Book Now and call us to schedule the time that is convenient for you! This tour includes a slice of Kermit's Key Lime Pie for each traveler & a bottle of water. What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
2 Hours
Key West
- Free cancellation
- Private tour
From
$549
No similar experiences found
Viator
Key West Spirits and Haunted Pub Crawl
Experience Key West’s top-rated haunted pub crawl, where chilling ghost stories, historic bars, and island cocktails come together for a night of spooky fun in the heart of Old Town. Led by passionate local guides who know the city by heart, you’ll uncover the dark history, haunted legends, and hidden secrets behind some of Key West’s most iconic locations. Along the way, visit legendary stops like Sunset Pier, First Flight Island Restaurant & Brewery, Curry Mansion Inn, Hard Rock Cafe Key West, The Oldest House Museum & Garden, and more haunted hotspots filled with tales of shipwrecks, restless spirits, and mysterious encounters. With eerie streets, unforgettable storytelling, and plenty of chances to grab a drink along the way, this ghostly adventure is the perfect mix of history, mystery, and nightlife!
2 Hours
Key West
- New
From
$36
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Viator
Pirates and Treasure: Self Guided Tour of Key West's Old Town
Embark on a self-guided audio adventure through Key West's storied Old Town, where the sun-soaked streets echo with the daring tales of pirates, treasure hunters, and fearless 'wreckers'. Led by the eccentric Captain William Shade, the ghost of an 1800s pirate, you'll navigate from Mallory Square to the Key West Shipwreck Museum. Duck into El Meson de Pepe's for rum-fueled revelry (drinks are not included in the price of the tour), explore Capt Tony's Saloon's ghostly history, visit the Oldest House Museum, and dive into Mel Fisher's Maritime Museum for tales of daring underwater heists. Encounter the wild past at Audubon House, and stand before the Custom House where customs agents once tamed the Key West tides. This is no ordinary stroll; it's a spirited awakening of history, where every step reveals the legends that shaped this island city. Best times for the tour are either early mornings or just before sunset, where the temperature can be a bit more pleasant.
1 Hour - 1h 15m
Key West
- Private tour
From
$30
No similar experiences found
Viator
Sandbar Snorkel Combo Adventure
This combo tour offers two experiences in one: a peaceful sandbar visit and an exciting snorkeling session. Unlike standard trips, you’ll enjoy a well-planned itinerary that maximizes your time on the water, with expert guidance and access to prime locations.
5 Hours
Key West
- Free cancellation
- New
From
$130
No similar experiences found
Viator
A Self-Guided Tour of Key West's Legends and Sights
Slip into Jimmy Buffett and Hemingway’s sandals and see iconic island sights on this self-guided audio tour. Key West’s quirky island lifestyle has attracted larger-than-life characters, including author Ernest Hemingway, singer Jimmy Buffet, and treasure hunter Mel Fisher. On this walking tour, you’ll hear about the legendary people the island has attracted over the years and see where they made history. Your guide is none other than Frank Everhart, the Schooner Wharf Bar’s very own comedic magician, whose tales are as captivating as the history they’re woven from. Frank, with his intimate knowledge and personal anecdotes, will show you the museums, bars and often-overlooked corners where treasure hunters, eccentrics, and unforgettable locals left their mark. You’ll even see Jimmy Buffet’s first home and his Key West recording studio, Shrimpboat Sound Studio.
1h 10m - 1h 30m
Key West
- Free cancellation
- Private tour
From
$20
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