Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour
Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll through the narrow, historic streets, you'll hear chilling tales of ghostly encounters, from restless spirits who never left to eerie legends passed down through generations. We’ll pass by the famous haunted landmarks, including the Key West Cemetery, where some say the dead still walk at night, and the eerie corners of Old Town, known for their strange, unexplainable occurrences. With the breeze in your hair and the moonlight casting long shadows, prepare for a spine-tingling ride into the heart of Key West’s most mysterious and supernatural stories. Buckle up, it's going to be a night you won't forget!
Duration: 1 hr 30 min
- Free cancellation
24' Hurricane Sundeck Boat Rental
The 24' Hurricane Sundeck stands out as the ultimate choice for families and groups looking for comfort and versatility on the water. Its spacious design and thoughtful features make every outing enjoyable and stress-free.
Why You’ll Love It:
Perfect Balance: Combines generous space with easy maneuverability for smooth cruising.
Room for Everything: Plenty of space for coolers, gear, and unforgettable memories.
Premium Features: Wraparound seating, built-in cooler space, Bimini shade top, stereo system, swim ladder, and a wide deck area for lounging.
Ideal for Any Occasion: Great for family outings, sandbar trips, sightseeing, or celebrating with friends.
Capacity: Comfortably accommodates up to 12 passengers.
Duration: 1 day
- Free cancellation
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.
Duration: 1 hr 15 min – 1 hr 30 min
- Free cancellation
- Private tour
Key West Nighttime Full Moon Sail
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moon comes up over Key West, enjoy star gazing opportunities and a moonlit sky as the boat glides through the majestic waters at night.
Duration: 1 hr 30 min
- Free cancellation
Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours
Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering hidden gems and local lore along the way .
Explore the vast wetlands of Everglades National Park, encountering unique wildlife and ecosystems . Delve into the rich history and biodiversity of Big Cypress National Preserve . Finally, discover the underwater wonders of Biscayne National Park, from coral reefs to mangrove forests .
With GPS-triggered narration, offline maps, and expert storytelling, enjoy the freedom to explore at your own pace without the constraints of group tours. Join thousands of travelers who have transformed their Florida road trips into enriching experiences—download now and let the Sunshine State's natural beauty and history captivate you!
Duration: 4 days
- Free cancellation
- Private tour
Key West to Key West Airport (EYW) - Departure Private Transfer
Book your private departure transfer from Key West hotels to Key West Int Airport (EYW).
Don't go through all the hassle of waiting in a long taxi or shared shuttle queue and use our private, door-to-door airport transfer.
Your driver will be waiting for you at a scheduled time, and you will travel comfortably to your destination. Meeting with a Nameplate and we will track your flight. We offer Door-to-door service. There is no hidden charges and we have clean cars and professional drivers
Duration: 15 min
- Free cancellation
- Private tour
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.
Duration: 2 hours
- Free cancellation
- Private tour
Florida Keys Sunset Cruise with Champagne Toast and Seafood
Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp when in season, offering an authentic taste of the Keys.
Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups looking to unwind while taking in panoramic views of the surrounding waters. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise.
Departure times adjust seasonally to align with the actual sunset, helping ensure the best possible experience on the water. Your confirmed departure time will be reflected in your booking confirmation.
Duration: 2 hours
- Free cancellation
Snorkeling in the Florida Keys
Unlike standard snorkeling trips, this activity offers expert guidance and access to prime reef spots known for their rich marine biodiversity. With a focus on safety and comfort, you’ll enjoy a hassle-free experience while exploring the underwater world.
Duration: 3 hours
- Free cancellation
Key West UFO Skywatch Tour with Night Vision
Search the skies over Key West for UFOs using powerful third-generation night-vision technology.
Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else in Key West. On clear nights, guests often spot multiple unusual objects moving through the sky, including lights and objects difficult or impossible to see with the naked eye.
You’ll use a professional night-vision scope valued at approximately $5,000 while Captain Heather helps distinguish satellites, aircraft and familiar objects from sightings that are harder to explain.
Groups are limited to just six guests, giving everyone plenty of time with the equipment and a clear view of the sky.
Come see what’s really moving above Key West after dark.
Viewing depends on weather and sky conditions. If conditions are unsuitable, you may reschedule or receive a refund.
Duration: 1 hr 15 min
- Free cancellation
Key West Odyssey: Uncover Island Secrets, Walk by Locals
Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic buildings with unique histories, uncovering tales of colorful figures who shaped the island, from renowned writers to influential locals.
As we stroll through beautifully preserved architecture, you’ll gain insights into the significance of each site, connecting with the spirit of Key West. This tour offers a chance to experience the essence of the island through its rich stories, creating an unforgettable adventure filled with intrigue and nostalgia. Don’t miss out on this magical journey!
Duration: 1 hr 30 min
- Free cancellation
Six Passenger Cart Rental
Our 6-passenger golf cart rental offers a fun, private, and convenient way for families and groups to explore Key West together. Instead of splitting up or relying on crowded tours, everyone can ride comfortably in one street-legal cart while discovering the island at their own pace.
With easy navigation through Old Town and quick access to popular spots like Duval Street, Mallory Square, and the Southernmost Point Buoy, it’s one of the most enjoyable and flexible ways to see the island.
Spacious seating, reliable performance, and the freedom to stop wherever you like make this a truly memorable Key West adventure!
Duration: 1–7 days
- Free cancellation
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.
Duration: 1 hr 30 min – 3 hours
- Private tour
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.
Duration: 1 hour – 1 hr 30 min
- Free cancellation
- Private tour
Key West Street Food Private Local Guided Tour
Embark on a personalized gourmet journey through the lively streets of Key West, where you'll savor a diverse range of street foods from succulent shrimp to iconic Key lime pie. This tour not only satisfies your taste buds but also immerses you in the rich cultural and historical backdrop of each dish. Led by expert guides, you'll uncover the fascinating stories behind the flavors and traditions that define Key West. Perfect for food enthusiasts and history buffs, this unique experience promises an unforgettable blend of culinary delights and cultural exploration.
Duration: 3 hours
- Free cancellation
- Private tour
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.
Duration: 3 hours
- Free cancellation
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.
Duration: 1 hr 10 min – 1 hr 30 min
- Free cancellation
- Private tour
Bahama Village Walking Tour
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.
Duration: 1–2 hours
- Free cancellation
Discover US East Coast Self Guided Audio Tour
Download GuideAlong’s self-guided audio tour bundle to make the most of your Eastern USA road trips. As you drive, hear stories play automatically as you explore scenic drives, national parks, lakeshores, and historic parks. This is the ultimate collection of 14 iconic destinations, including Acadia, Blue Ridge Parkway, Catskills, Florida Keys, Great Smoky Mountains, Lake Superior, Outer Banks, Shenandoah, and Vermont’s Route 100. A memorable adventure awaits on America's iconic roads.
Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t.
Stories, tips, and directions play automatically based on your location
Travel at your own pace
Tour offline using GPS. No cell service or WiFi is needed
Suggested itineraries for half, full, or multi-day use
Buy once, use forever! No expiry, includes free updates
Like having a tour guide along for the drive
Purchase one bundle per vehicle.
Duration: 7 days
- Free cancellation
- Private tour
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.
Duration: 2 hours – 2 hr 30 min
- Free cancellation
- Private tour
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.
Duration: 1 hour – 1 hr 15 min
- Private tour
Polaris Slingshot
Turn your trip into something unforgettable with a Polaris Slingshot rental from Keys Vacation Supply Rentals. This open-air ride lets you feel the ocean breeze, soak in panoramic views, and enjoy the road like never before—all while being easy to drive with a standard license. With built-in navigation, premium sound, and flexible rental options, you can explore at your own pace and make every mile part of the adventure. It’s more than just transportation—it’s the highlight of your vacation waiting to be booked.
Duration: 1 day
- Free cancellation
Key West: Morning Snorkeling Breakfast & Drinks, Conch Train
Early Bird Snorkel gets you to the Worlds 3rd largest living coral reef as we sail towards our destination enjoy breakfast, draft beer & unlimited mimosas. As you return you can jump on the Hop off Hop On bus and doing this tour.
Conch Train
Duration: 5–8 hours
- Free cancellation
Private Marathon Backcountry Fishing Charter
Experience a side of the Florida Keys that can only truly be appreciated from the water. Marathon provides access to an incredible network of shallow flats, mangrove-lined backcountry, and clear tropical waters where anglers can pursue some of the Keys' most celebrated game fish.
Depending on the season and conditions, target tarpon, bonefish, permit, snook, and other species while exploring the surrounding backcountry with an experienced local captain. The shallow-water setting creates a more intimate fishing experience where spotting fish, making the right cast, and watching the action unfold can be as exciting as the catch itself.
Fish from a modern skiff or flats boat with rods, reels, tackle, and necessary safety equipment provided. Combining personalized fishing, iconic Florida Keys species, and beautiful backcountry scenery, this private Marathon charter delivers an unforgettable shallow-water adventure.
Duration: 4 hours
- Free cancellation
- Private tour