Key West
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Viator
Dark Corners of Key West Private Walking Tour
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.
5.0(1)
2 Hours
Key West
- Free cancellation
- Private tour
From
$392
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Viator
Robert the Doll After Dark
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.
5.0(1)
1 Hour
Key West
- Free cancellation
- New
From
$45
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Viator
Private Looe Key Snorkel from Big Pine Key
Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef system after the Great Barrier Reef in Australia, and the Palancar Reef in Mexico and Belize. It is a special place for snorkeling.
5.0(442)
3 Hours
Key West
- Free cancellation
- Private tour
From
$599
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Viator
Custom Charters with a Local Captain
These Tours are unique because they are offered by a seventh generation local who knows the waters and can take you to places other people can’t. This completely custom and private tour so start Band end times are charla e upon guests request. You will have a great day on the water looking at dolphins snorkeling going to sandbars swimming and taking in the beautiful scenery.
5.0(48)
3h 30m
Key West
- Free cancellation
- Private tour
From
$250
No similar experiences found
Viator
Southernmost Key West History and Culture Small-Group Walking Tour
Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience and discovery, not just monuments and museums. You want to understand what’s behind the touristic façade that most people never penetrate. That’s why the Southernmost Walking Tour is the best way to immerse you into the history and culture of Key West! When you’re on foot, the world can’t slide past you faster than you can absorb it. You’ll have time – and proximity – to get up close to the region’s culture and natural history. Start your tour at the famous Cuban sandal factory - Kino Sandals before heading off toward the Southernmost Point of the continental United States. Along the way, our incredibly knowledgeable and well-connected local guides will show you the most popular landmarks and introduce you to local culture. By the time you’re finished, you’ll have a uniquely fun perspective of our tiny island!
5.0(136)
1h 45m
Key West
- Free cancellation
From
$50
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Viator
Key West Historic Bahama Village & Hemingway Heritage
Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key West was discovered and became so rich? Explore Key West’s history, lore, and legends from the ground up with an intimate walking tour. Whether you want to learn more about the island’s first industries such as shipwrecking and cigarmaking, are curious about local history, or are looking for a fun-filled walk, Key West’s Historic Districts are waiting for you! This small-group walking tour offers both an educational experience and unparalleled delight for the lovers of history and culture. Our experienced local tour guides will lead you on an impressive stroll through the scenic streets of the Old Town where you can connect with the culture of a historic city. This unique experience is enjoyed by visitors from across the world and is a must-do while in Key West! What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
5.0(256)
1h 30m
Key West
- Free cancellation
From
$57
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Viator
Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and being on the water in Key West. I now own a small business with my wife and 2 young kids. We are trying to make a big impact by educating and leading by example. I'm very passionate about being respectful to the wildlife and the environment
5.0(192)
4h 30m
Key West
- Free cancellation
From
$156
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Viator
Key Lime Pie Walking Tour of Key West Historic Seaport
Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, and fully obsessed with the island’s iconic slice, this small-group tour is a feast for all your senses. Wander the Historic Seaport while savoring three decadent Key Lime Pie tastings, each with its own tropical twist, and sip a refreshing Key Lime cocktail. Along the way, your guide shares insider tales, quirky legends, and secret local spots you won’t find in any guidebook. Fun, flavorful, and unforgettable—this is the Key West experience you’ll be raving about long after the crumbs are gone.
4.9(50)
1h 30m
Key West
- Free cancellation
From
$70
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Viator
Key West Wreckers Race Aboard Schooner America 2.0
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern coast of Key West. When all the sailors in Key West heard there was booty to be had, they'd get in their boats and race each other out to the reef. The first one there could claim the ship's cargo. Today, we celebrate it with the firing of the canon to start the race, and all of the schooners of Key West are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, "wins"!
4.9(14)
3 Hours
Key West
- Likely to sell out
From
$116
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Viator
Personalized Key West JetSki Tour for Small Groups Nearly Private
Almost Private Jet Ski Tour – Voted Key West’s Best Get ready for the most exclusive jet ski experience in Key West. With only 2 to 3 jet skis per outing, this tour offers the closest thing to a private adventure on the water. It's the perfect way to explore the island without the crowds — just you, your guide, and the open ocean. Voted Key West’s Best Jet Ski Tour and backed by over 15,000 five-star reviews, this small-group tour circles the entire island on a 28-mile guided ride. You'll stop at iconic landmarks like the Southernmost Point, a hidden local sandbar, and scenic spots throughout the Florida Keys Nature Sanctuary. Drivers and riders can switch at the stops, so everyone gets a turn behind the handlebars. There are no hidden fees — everything is included. You’ll enjoy a free second rider, complimentary shuttle pickup (based on availability), and all fuel and safety equipment provided at no extra charge.
4.9(51)
1h 30m
Key West
- Free cancellation
From
$169
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Viator
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to Marathon and stop along the way to explore the natural splendor and man-made wonders of the Florida Keys. Such stops will include the Florida Keys Aquarium Encounters, Bahia Honda State Park, and the Blue Hole on the National Key Deer Refuge. Your driver will provide fun and interesting commentary along the way. This tour will have a maximum group size of 12, with filtered water, lunch, and entry fees included. Customizable for private tours, call to make your tour private!
4.9(36)
7 Hours
Key West
- Free cancellation
From
$169
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Viator
Dinghy Drinking Tour through Key West Waters
On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to 5. An experienced licensed boat captain who knows the waters will lead your tour. Dinghies can go through narrow tunnels in the mangrove trees that bigger boats cannot get through. Be ready to duck under branches. We will stop at waterfront bars. 2 or 3 stops depending on your preferences. If your group is larger, we will arrange additional boats. You can get in the water to swim or wade at any time. You will see lots of fish and sea creatures. Most of our guests bring beer, water or other beverages along for the tour. We have coolers to keep them chilled.
4.9(107)
3 Hours
Key West
- Free cancellation
From
$85
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Viator
Key West Craft Cocktail Crawl
Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era, each of it’s 5 stops revealing a new secret. Travel off Duval Street and into neighborhood bars that locals frequent! Sample delectable bites and nibbles between drinks to get a taste of what the island life is all about. Curated with fun-lovers in mind, this upscale bar crawl is ideal for those who are more inclined to mingling and exploring Key West’s vibrant bar scene. Tastings include asian cauliflower bites, taco of your choice, 4 delicious hand crafted cocktails, locally-made beer, and much more. Our group size is limited to 12 people to ensure personal service from the guide.
4.9(569)
3 Hours
Key West
- Free cancellation
- Likely to sell out
From
$94
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Viator
PRIVATE Welcome to Key West Walking Tour
Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. This is private tour is customizable, meaning you can request to adjust the meeting point to better suit your day, and even request what kind of stories you'd like to hear. Perfect for wedding party, couples, family & friends, bachelor/bachelorette, birthdays, reunion, corporate groups, and more! If it's too far or too hot to walk, you can hop on the Duval Loop bus with your guide It's air-conditioned with several convenient stops throughout Old Town. The best part about your own private tour is you can ask questions and customize the tour to your interests! Feel free to include notes in your booking about: - what you want to know about Key West - points of interest you'd like to include - if you're celebrating an event - mobility challenges or other needs we can accommodate Total distance about 1 1/2 miles.
4.9(22)
1h 30m - 3 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$138
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Viator
Key West Mangrove Kayak Eco Tour
Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key West. You will glide through the winding mangrove creeks and paddle through inches of water, where you can easily view and learn about the geological structure of the Keys along with its inhabitants, all from the comfort of your kayak. Your adventure will give you a chance to view the mangrove environment up close, along with its marine life including tropical fish, crabs, sea stars, jellyfish, sea cucumbers, sponges and various aquatic birds. Every trip leads us on a different adventure! all guests must know how to swim. Rest rooms to change on site. No lockers but things can be left behind at paddle shack. Beginners welcome!
4.9(2341)
2 Hours
Key West
- Free cancellation
From
$80
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Viator
Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset
This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters of the Key West National Wildlife Refuge—a remote area only accessible by boat. With group sizes limited to 20 guests, the experience feels personal, spacious, and relaxed! Our crew truly sets us apart. They’re knowledgeable, passionate, and always ready to share the history, wildlife, and ecology of the Keys in a fun, engaging way. Whether you're in the water or relaxing on deck, they’re there to guide, support, and make everyone feel welcome—regardless of experience level. Snacks, beer, wine, soda, and water are included onboard, adding to the comfort of your time at sea. If you join the afternoon trip, you'll also enjoy a beautiful sail back to Key West timed with the sunset, making the day even more memorable.
4.9(1759)
4h 30m
Key West
- Free cancellation
- Likely to sell out
From
$125
No similar experiences found
Viator
Southernmost Food & Cultural Walking Tour by Key West Food Tours
Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in historic old town, dining on typical Cuban dishes, local seafood, and of course -- Key Lime Pie. Food samples are enough for a hearty lunch. Between tastings walk like a local, away from the touristy streets, as your guide shares insights about city history, food and architecture. This is a small-group tour, with a maximum of 12 people, ensuring a personalized experience.
4.9(1874)
3 Hours
Key West
- Free cancellation
- Likely to sell out
From
$90
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Viator
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Included in the tour price is bottomless house champagne Chandon Brut, 8 premium red and white still wines, ice-cold beers & White Claws, and a champagne-inspired Gourmet Cheese Buffet (naturally gluten free) that includes 4 incredible international cheeses, paired plump berry tray, local smoked fish dip, crunchy crisps and fresh-baked crusty bread. Two other Moët & Chandon champagnes are available for additional purchase - both at wholesale price - only for onboard guests. Key West is famous for its tropical sunset, and there’s no better way to watch it than on this famous Sunset & Moët Cruise. This public trip is always limited to 14 adult passengers on a 28 person sailing catamaran, for guests comfort and quality control. And NO kids!
4.9(987)
2 Hours
Key West
- Likely to sell out
From
$109
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Viator
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands in the Key West National Wildlife Refuge. Keep an eye out for dolphins, sea turtles, manta rays and many other wildlife that call the Refuge home. Your captain knows where dolphins are frequently seen and will let you know if he spots any. Upon reaching the mangrove islands, the schooner anchors and your exploration begins. Your day is divided between guided kayaking tours and guided snorkeling tours. The warm, shallow water is calm, sheltered by the uninhabited mangroves, making kayaking a breeze. After your tours, come back aboard and wash off with our fresh water rinse, and relax on deck. Choose from plenty of complimentary cold drinks – frosty cold beer, wine, homemade sangria, chilled sodas and filtered water. This is the best of laid-back island living.
4.9(102)
5 Hours
Key West
- Free cancellation
From
$119
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Viator
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure
Explore the serene mangrove waterways of Geiger Key on this guided eco-tour. Perfect for all ages and levels of experience. Choose between a single kayak, double kayak, or stand-up paddleboard as you glide through the lush scenery. Your knowledgeable guide will point out the hidden gems of this unique Florida Keys ecosystem, ensuring a memorable and educational experience. With safety gear, paddle instruction, bottled water, and dry bags provided, all you need to bring is your sense of adventure. Enjoy complimentary shuttle pick-up from Key West and immerse yourself in nature for two hours of tranquility.
4.9(18)
2 Hours
Key West
- Free cancellation
From
$75
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Viator
Key West Historic Seaport Food & Walking Tour
Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood options) cuban sandwich & key lime pie tastings. Sample classic ingredients like Key West pink shrimp, Caribbean warm-water lobster, and fresh fish. Sip white wine after walking through the tropical neighborhood streets. This small-group tour is limited to 12 people, and you'll leave with a greater understanding of the industries that shaped our island and culture. Joining a fish lover, but not one yourself? No problem, we’ve got you covered with equally delicious substitutions.
4.9(671)
3 Hours
Key West
- Free cancellation
- Likely to sell out
From
$93
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Viator
Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters
Experience the Florida Keys like a true Conch! Our 4-hour Backcountry Sandbar Excursion takes you to a stunning location chosen by your captain based on the day's weather and tides. Immerse yourself in the intoxicating beauty of turquoise waters and deep blue skies. Keep an eye out for the incredible local wildlife – you might spot rays, turtles, fish, and even playful dolphins! Once we arrive at the sandbar, you'll have ample time to swim, soak up the sun, and simply unwind in this island paradise. Just bring your swimsuit, towel, sunscreen, and any snacks and drinks (including alcohol) you'd like to enjoy. This private trip is perfect for up to 6 passengers and runs daily from noon to 4 pm.
4.9(136)
4 Hours
Key West
- Free cancellation
- Private tour
From
$565
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Viator
Sandbar Adventure Cruise in the Florida Keys
Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your spacious 52’ catamaran, complete with complimentary snacks and drinks while soaking up the sun or exploring the crystal-clear waters. Your experienced crew will ensure a smooth sailing experience, showcasing the best spots in the area. Perfect for groups seeking relaxation, celebration, or exploration, this tour promises unforgettable memories in paradise. - Enjoy a leisurely sandbar trip with paddleboarding and floats - Experience breathtaking sunset views while sipping drinks - Spacious and comfortable 52’ catamaran with Wi-Fi - Friendly and knowledgeable crew dedicated to your safety and enjoyment
4.9(8)
4 Hours
Key West
- Free cancellation
- New
- Likely to sell out
From
$85
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Viator
Guided Clear Kayak Eco-Tour Near Key West
100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the blueish-green waters. Eco-Tours with Marine Viewing: Our eco-tours immerse you in the rich ecosystem of the Florida Keys. Watch for starfish, nurse sharks, jellyfish, stingrays, and many other marine creatures as they go about their daily lives just inches beneath your kayak. Journey through Mangroves: The tour takes you through the pristine mangroves of Sugarloaf Key, offering a scenic and serene experience that's both refreshing and educational. You'll get to witness the delicate balance of life in these important coastal habitats. If the tide is too low or too high, your guide may adjust the route to ensure the best experience. Expert Guides: They're trained to prioritize safety while sharing interesting facts about the area's marine life and ecosystem.
4.9(700)
2 Hours
Key West
- Free cancellation
- Likely to sell out
From
$79
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