Key West
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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
Private 90-Minute Harbor Sailing Charter in Key West
Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some friendly dolphins off the bow!
4.9(19)
1h 30m
Key West
- Free cancellation
- Private tour
From
$395
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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
Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat
Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an hour and fifteen minutes prior to sunset so we can get to the perfect place to watch the sunset. Our boats feature a large thatch roof for shade, bluetooth tv and stereo, a walk in bathroom, adjustable padded bar stools and a gorgeous live edge tiki bar. You'll cruise the Key West harbor in style and view the famous sunset on your private 2 hour adventure. Keep your eyes on the horizon for a chance to see the famous Green Flash as the sun goes down.
4.8(68)
2 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$457
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Viator
Florida Key West Self-Guided Walking Audio Tour
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.
4.7(25)
2 Hours - 3 Hours
Key West
- Free cancellation
- Private tour
From
$10
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Viator
Private Key West Sunset Sail
2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for the perfect Key West sunset sail Peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks, bottled water and coolers stocked with ice provided for any adult beverages you choose to bring. Reserve ahead, there is after all, only one High Tide sunset sail per day! Price is for up to 6 guests, 12 guests max!.
4.7(52)
2 Hours
Key West
- Private tour
- Likely to sell out
From
$695
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Viator
Maritime Village to Micro State: A Self Guided Tour of Key West
Key West is famous as mainland America's Caribbean resort town. Here, time slows down as the island vibes take over. But there is more to this island than umbrella drinks and warm breezes. Key West has an incredible history, from its origins as a maritime village that profited heavily from salvaging wrecked ships and crews along the Great Florida Reef a few miles offshore, to the creation of the micro-state known as the Conch Republic. While in Key West, you will want to visit many of the sites that make the island distinct such as the Key West Lighthouse, the Hemingway House, the Little White House, and Southernmost Point. On this tour, you will visit all of these and more, stopping for refreshments along the way at many of the island's signature restaurants and bars. You will hear stories of some of the island's more famous residents along with some lesser-known tales that have given Key West its unique place in American culture and history.
4.7(3)
1h 30m - 3 Hours
Key West
- Private tour
From
$12
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Viator
Key West Boat Experience — Swim, Sip & Soak Up the Sun!
Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a half-day adventure aboard our luxurious Manitou Cruise—a spacious, smooth-riding tri-toon with a deluxe swim deck, perfect for soaking up the Key West sun in comfort and style. Guided by one of our licensed, experienced captains, your private charter explores the untouched beauty of Key West’s backcountry—customized to your pace and preferences. Cruise to local sandbars, glide through scenic mangroves, or venture farther to spots like Mud Key, Snipes Point, and the Dolphin Playground, where wild dolphins often play in their natural habitat. Swim, snorkel, relax on remote beaches, or simply enjoy the ride with a drink in hand—it’s your trip, your way. Perfect for families, couples, or small groups seeking a flexible and private escape into the real Key West.
4.5(10)
4 Hours
Key West
- Free cancellation
- Private tour
From
$600
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Viator
Key West’s Old Town Treasures: A Self-Guided Audio Tour
See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour. • Find out how the town nearly went bankrupt before reinventing itself as ‘The Conch Republic’ in the 1900s • Hear from producer Ed Owen, a seasoned Key West traveller and tour guide • Do it all in 90 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home • This tour does not enter or include entry to any of the attractions mentioned en route Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.
4.3(29)
1h 30m - 2 Hours
Key West
- Free cancellation
- Private tour
From
$15
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Viator
Private 2-Hour Tiki Boat Party in Key West & Mini Sandbar
Set Sail for Tiki Revelry in Key West's Historic Seaplane Basin! Cruise to Key West's unique Seaplane Basin. In the early 1900s, this spot buzzed with activity as seaplanes took off and landed. Today, it's a vibrant harbor where colorful houseboats bob gently, creating a charming island atmosphere. Gear up for an afternoon of tropical fun on our 2-hour Tiki Boat Party & Mini Sandbar Escape! Let your captain navigate the turquoise waters as we head to a secluded swimming hole, the perfect setting for a tiki celebration.
4.3(7)
2 Hours
Key West
- Free cancellation
- Private tour
From
$403
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Viator
Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader
Go at your own pace and schedule. You'll see Key West's most haunted spots and hear their ghostly stories on spooky solo walking tour on the WalknTours App. 1 purchase works on 2 smartphones. BOGO! Avoid large tour groups. Hear every word. Optionally read the dialogue. Once you unlock the tour it does not expire and can be taken anytime. This offers spooky narration, theatrically crafted and music infused tour you can take anytime. Contactless and social distance friendly. It's recommended to listen on headphones or earbuds. Also you can Listen on a bluetooth speakers or your phone speaker. What makes this tour special? -The spooky narrator is one of a kind. -This is not a fact dumping tour. It's a spooky adventure. -Go anytime. Go at your own pace -Great bang for your buck. Get the adventure for a fraction of the price of other tours.
4.2(9)
40 Minutes - 55 Minutes
Key West
- Free cancellation
- Private tour
From
$10
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Viator
Key West History Audio Guided Walking Tour
You may have heard the island of Key West called many different things – America’s Caribbean Island, Margaritaville or The Conch Republic. But you know what we locals call it? Paradise!! And I bet by the end of our tour you will agree with me. Go at your own pace. This is a smartphone guided tour that uses GPS to direct you step by step on a hands free adventure.
4.0(4)
1 Hour - 1h 30m
Key West
- Free cancellation
- Private tour
From
$10
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Viator
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
Dry Tortugas National Park Day Trip by Luxury Private Boat
Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury boat, ensuring a swift and comfortable journey through the stunning turquoise waters to Dry Tortugas National Park. Revel in top-class amenities perfect for sunbathing, sightseeing, and relaxing with your private group. Discover secluded islands and pristine tropical beaches on this guided full-day adventure. History buffs will be captivated by Fort Jefferson, while outdoor enthusiasts will relish the world-class snorkeling and breathtaking natural beauty. This unique voyage combines exhilarating open-sea travel with an intimate and personalized experience, creating memories that will last a lifetime.
3.9(11)
8 Hours
Key West
- Free cancellation
- Private tour
From
$1,500
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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
The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise
Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the sky transforms into a vibrant canvas of colors, providing an unforgettable backdrop for your evening. Bring your favorite beverages to toast the day's end in a romantic and relaxing atmosphere. Capture unique photo opportunities with breathtaking reflections in the water, making this experience perfect for couples or anyone looking to unwind after a day of exploration. - Enjoy a serene 2-hour cruise on the tranquil waters of the Florida Keys - Front-row seat to a spectacular sunset with unobstructed views - Bring your own beverages for a personal touch during the cruise - Perfect for couples or those seeking a relaxing escape after sightseeing
2 Hours
Key West
- Free cancellation
- Private tour
- New
From
$599
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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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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
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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
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
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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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