History Nature and Culture of Key West Walking Tour
This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local guide, you'll discover how nature, history & community shaped Key West into the unique place it is today. With a small-group setting, you'll enjoy a personal experience filled with stories, insights & local knowledge that most visitors never hear.
Duration: 1 hr 30 min
- Free cancellation
Kooky Key West Scavenger Hunt
Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment!
Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!
Duration: 2 hours
- Free cancellation
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.
Duration: 2 hours
- Free cancellation
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*
Duration: 7–8 hours
- Free cancellation
- Private tour
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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.
Duration: 2–3 hours
- Free cancellation
- Private tour
Petals and Vines Boutique Craft Café
Unlike traditional art classes, here you choose your own creative adventure.
Located inside a charming boutique at The Shops at Mallory Square, this one-of-a-kind experience combines crafting, shopping, and the relaxed atmosphere of Key West. Guests can select from a rotating menu of hands-on projects, including pressed floral bookmarks, decoupage teacups and saucers, decorative birdhouses, seasonal crafts, and more.
No two visits are the same. With new projects introduced regularly, there's always something fresh to create.
Duration: 1 hour
- Private tour
Key West Airport Private Hotel Transfer up to 5 passengers
If Your Flying Into or Out Of The City, Allow The Chiefton Group To Meet You There or Get You
There… Get Curbside Pick Up / Drop Off Service. Enjoy The Scenic Ride From and/or The Scenic
Ride Back to The Airport.
Duration: 1 hour
- Free cancellation
- Private tour
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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.
Duration: 1 hr 30 min
- Free cancellation
- Private tour
Key West Private 6-Person Sandbar & Snorkeling Charter
Your Day, Your Way!
Step aboard our 24’ center console and discover the best of Key West’s stunning waters! Perfect for groups of up to six people, this private, captain-guided adventure takes you through crystal-clear waters to beautiful sandbars and unspoiled beaches that can only be reached by boat. With comfortable seating and a T-top for shade, you’ll have everything you need for a fun and relaxing day exploring the breathtaking beauty of the Florida Keys!
Duration: 4 hours
- Free cancellation
- Private tour
Key West 2-Hour Guided Jet Ski Island Tour – 28-Mile Full Lap
This is the only full two-hour guided jet ski tour in Key West. The 28-mile island lap provides approximately 30 minutes more riding time than a typical 90-minute tour, allowing for a more complete route and several scenic stops when conditions permit. Ride a stable Yamaha WaveRunner VX while an experienced local guide manages the route according to tides, weather, marine traffic, and safety conditions. Shared and private options may be available, with groups limited to a maximum of six jet skis.
Duration: 2 hours
- Free cancellation
Key West's Morning Jet Ski Tour Special
Earlybird Jet Ski Tour – Key West’s Best Deal on the Water
Start your day with adrenaline and savings on our Earlybird Jet Ski Tour, the first trip out on the water and the best value of the day. This exclusive morning tour offers all the thrills of our award-winning 28-mile island ride — at a discounted rate.
Voted Key West’s Best Jet Ski Tour and backed by over 15,000 5-star reviews, this guided adventure takes you around the entire island with scenic stops at the Southernmost Point, a hidden local sandbar, and inside the protected Florida Keys Nature Sanctuary. It’s the perfect mix of speed, sightseeing, and serenity — all before most visitors have finished breakfast.
No hidden fees. No surprise charges. Your tour includes a free second rider, complimentary shuttle pickup (based on availability), and all gear and fuel. Our expert guides ensure a safe, exciting ride while giving you space to explore. Drivers and riders can switch during stops, making it even more fun for both.
Duration: 1 hr 30 min
- Free cancellation
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.
Duration: 2 hours – 2 hr 30 min
- Free cancellation
- Private tour
Private Marathon Reef Fishing Charters
Explore the productive reefs of the Florida Keys on a private Marathon reef fishing charter into the Atlantic. Marathon provides convenient access to an incredible reef system where your captain can target a variety of species while surrounded by the clear tropical waters that make the Keys famous.
Depending on the season and conditions, target snapper, grouper, sharks, jacks, and other reef species using techniques such as drift fishing, bottom fishing, and deep dropping. Your local captain will select fishing areas and techniques based on current conditions and what's active.
One of the highlights comes after the fishing. Your legal catch can be cleaned at the dock, giving you the option to take your fish with you or explore local opportunities to have your fresh catch prepared. Combining diverse reef fishing, beautiful Florida Keys scenery, and a memorable catch-to-table experience, this private charter offers a unique way to experience Marathon from the water.
Duration: 4 hours
- Free cancellation
- Private tour
Key West Attractions Pass with Trolley Tour
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
Duration: 1 hr 30 min
- Free cancellation
4 Hours Pontoon Rental in Key West
Create your own adventure: fish, snorkel, paddleboard, or just cruise in style! The newest fleet in town! Our spacious pontoons provide plenty of space and shade while you make your way through our beautiful local waterways!
What’s Included:
12 Passenger Pontoon Boat Rental (Children and babies count as passengers)
Safe, reliable, and well-maintained equipment
Includes a 70qt cooler (purchase ice at check-in)
Life vests for all passengers
Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+
Optional Add Ons:
Paddleboards- A fun and suitable activity for people of all ages and abilities.
Lily Pad- This floating foam island allows you to rest, kick-back, tan, run, and play on.
Duration: 4 hours
- Free cancellation
Private Sandbar Adventure in Key West Backcountry
*Visit Stockislandboatcharters.com for alternate availabilities and pricing.*
Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch for wildlife throughout the trip such as dolphins, sea turtles, fish, birds, and much more! A cooler filled with ice and bottled water will be provided. Feel free to bring any food or alcoholic beverages.
Duration: 3 hours
- Free cancellation
- Private tour
Key West Custom Perfume Making Class with Champagne Toast
Step into our light, island-chic fragrance lab on Duval Street to craft your own custom luxury perfume or cologne. Guided by an expert perfumer, you'll sample from a curated "organ" of over 300 premium oils, blend your signature scent drop-by-drop, and take home a full-sized 55ml bottle. Celebrate your creation with a complimentary Champagne toast in a beautifully air-conditioned sanctuary away from the Key West heat!
Duration: 1 hr 30 min
- Free cancellation
Sunset Cruise
Come see for yourself why Marathon Mermaid is voted the #1 thing to do in Marathon! Watching the sunset by water is a must-do when visiting the Keys!
Duration: 2 hours
- Free cancellation
Florida Keys Nature & History Tour from Key West
With your friendly and knowledgeable tour guide, this 4 Hour VIP Tour of the South Keys promises to amaze you. En route, you’ll learn the history, culture, and ecology of the Keys, listen to island music, and enjoy the breathtaking scenery! Feel free to ask questions, share your experiences, and point out wildlife.
* We drive you from island-to-island on the iconic Overseas Highway, about 45 miles from Key West & over 20 bridges
* Revel in the scenery as we drive over the iconic 7-Mile Bridge - twice!
* Experience world-famous Bahia Honda State Park: dip your toes in the Gulf of Mexico AND the Atlantic Ocean, walk on a historic railroad bridge for spectacular views, and more!
* Photograph endangered Key Deer on Big Pine Key on our world-famous Key Deer Safari
* Visit the Blue Hole to check for alligators and other native wildlife
You'll love this tour so much, you'll book it again next year!
We sanitize our tour vehicles before each tour in accordance with CDC recommendations.
Duration: 4 hours
- Free cancellation
Ghosts of Key West: Haunted History Walking Tour
Discover a darker side of Key West on a 90-minute walking ghost tour through the historic streets of Old Town. Led by an engaging Ghost City Tours Ambassador, you'll uncover the island's haunted history at landmarks including St. Paul's Episcopal Church, The Artist House, Audubon House, La Concha, and Marrero's Guest Mansion.
Along the way, hear stories of the people, tragedies, legends, and reported hauntings that have become part of Key West's history—including the story surrounding Robert the Doll. Designed for families, history lovers, and curious travelers, this after-dark walk blends documented history with the ghost stories that have followed Key West for generations.
Duration: 1 hr 30 min
- Free cancellation
Marathon Key: 3-hour Snorkeling adventure on a Pontoon at Sombrero Reef
Enjoy a 3-hour snorkeling adventure in Marathon Key at one of the world's most incredible reefs. Sombrero Reef is alive. It is a place where parrotfish feed on the living coral while trumpetfish try to blend in among its branches. The reef is protected, so you can expect to see large schools of grunts and snappers swimming among large groupers hiding in the crags and looking for a meal. The great barrier reefs on our planet are precious. Like underwater rainforests, they teem with wildlife and colorful corals.
You are welcome to bring food and drinks with you.
Duration: 3 hours
- Free cancellation
Private Key West Sandbar and Paddle by Boat
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Paddle on your own via kayak or paddleboard through natural, winding, mangrove lined tidal creeks and then relax on a sandbar or island on one of our floats. Bring your own snacks and drinks and your dog!
Duration: 3 hr 30 min
- Free cancellation
- Private tour
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.
Duration: 1 hr 30 min – 3 hours
- 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).
Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer.
Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination.
We track your flight. Our driver greets you with a name plate. We provide door-to-door service. There are no hidden charges. We use clean cars and professional drivers.
Duration: 25 min
- Free cancellation
- Private tour