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!
Private Island & Fishing Charters in Key West 37ft Knotty Cowgirl
Experience the best of both worlds with our Island Fishing Tour, exclusively offered by Cowboy Cowgirl Sportfishing Charters. Unlike typical fishing charters, this unique excursion combines thrilling fishing action with serene island exploration. Cast your line in prime fishing spots, then hop between picturesque islands where you can take a break and enjoy your own picnic. Perfect for those who love both adventure and relaxation, this tour offers an unparalleled opportunity to catch the big one and discover the hidden gems of our beautiful coastline. Whether you're an avid angler or simply looking to enjoy a day on the water, our Island Fishing Tour promises an unforgettable experience.
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.
Tropical Drift - A Key West Sunset Cruise
Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests
Leave the crowds behind and experience the magic of a Key West sunset from the water on your own private 2-hour cruise aboard a brand-new Manitou luxury pontoon. Departing from the tranquil Cow Key Channel, you'll enjoy a relaxed and intimate journey through hidden backchannels and open waters — all with a front-row seat to one of nature’s most unforgettable shows.
Cruise in comfort with up to 10 guests, guided by a licensed local captain, and take in stunning views of the sunset-drenched coastline, including iconic sights near Mallory Square — without ever getting caught in the crowd.
Whether you're planning a romantic evening, a family outing, or a fun get-together with friends, this cruise offers the perfect mix of laid-back luxury and scenic beauty.
Reserve your sunset escape now — and experience Key West the way locals love it: peaceful, personal, and absolutely stunning.
Private Sunset Sail in Key West Florida
Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life.
Take the helm, learn how to raise and trim the sails, or just sit back and relax.
Enjoy a private sunset cruise off the coast of Key West See the sites of Key West from the water Snacks and beverages included Fun for an entire group or family Private guides for a more personalized experience.
Enjoy a private sunset sail off the coast of Key West and see the sights of Key West. Bring your favorite alcoholic beverages to enjoy while watching the sunset. Knowledgeable Captains to explain the art of sailing.
Elope in Key West Intimate Wedding 10 Guests or Less
Looking for a simple easy way to elope in Key West - look no further - our professional photographers are also officiants and so they provide a combo - they marry you then photograph this lifetime moment. Our professional will meet you at the desired location - will perform the ceremony then will photograph the format of the ceremony and some couple photos after - total event will be 1 hour - NO decor is included.
Private Key West Fishing & Sandbar or Snorkel Charter
1 Traveler is equivalent to reserving the entire boat. (Up to 6 Guests)
Explore the vibrant waters of Key West on a fully custom private charter designed for up to 6 guests. Enjoy family-friendly bottom fishing, where all bait and equipment are provided, ensuring a fun-filled fishing experience. We will be targeting grouper, barracuda, yellowtail snapper, mangrove snapper, sharks & much more.
After reeling in your catch, choose between relaxing at a stunning sandbar or go on a reef snorkeling adventure in crystal-clear waters with our expert captain guiding you to the best spots. Dive into this unforgettable adventure that caters to families and ocean lovers alike, complete with all necessary gear for both activities.
Highlights
- Private 4-hour charter for up to 6 guests
- Family-friendly bottom fishing with included bait and equipment
- Choose between a beautiful sandbar experience with lily pad float or snorkeling
- All snorkeling gear provided for your convenience
Dolphin Watch, Snorkel, Open Bar & 1 Day Hop-On Hop-Off
This is the best 1 day combo where you will enjoy the water and land in Key West. Get to Hop On Hop off the conch train, one of Florida's most popular attractions, going to Truval Village: Steps away from the Ernest Hemingway Home and Museum, the Key West Lighthouse, the Southernmost Point and Key West Butterfly and Nature Conservatory. Start the day with a Catamaran adventure going Delphine watching and then snorkeling in 1 of the worlds largest reefs. We may even see sea turtle and other exotic fish.
On the return enjoy and open bar that includes well mixed drinks, draft beer, margaritas, rum runners and a great selection of wine & champagne.
As an added benefit join us at the Sails and rails museum to learn our history.
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!
Marathon Florida Keys Fishing Experience Big Game
We love what we do ! We cater to private groups and families. We have one of the best fisheries in the world and we pride ourselves on giving customers a unique experience here in the beautiful Florida Keys. Let us help you create some great memories.
Advanced Wreck Diving at USNS General Hoyt S. Vandenberg
The USNS General Hoyt S. Vandenberg, a retired Air Force missile tracking ship, lies 160 feet beneath the waves, offering advanced certified divers an unparalleled underwater adventure. Explore its expansive 520-foot structure, where vibrant coral and diverse marine life thrive. Navigate through radar dishes, intricate passageways, and expansive decks, all teeming with fish, turtles, and majestic Goliath groupers. This signature dive in Key West promises unforgettable photo opportunities and a chance to witness the beauty of an artificial reef, making it a must for any experienced diver's bucket list.
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.
Key West UFO Tour
Key West's most mind-blowing sky watch! Search for UFOs with your military-grade night vision scope as we blow your mind with tales of UFOs, UAPs, alien encounters, and the hidden history of UFOs in Key West. Small groups, local guides, little-known history, and oceanfront viewing sites make this a unique, unusual, unforgettable experience. Your $5000 night vision scope will change how you see the night sky forever. This experience is dependent on suitable viewing conditions. If we cancel you will have the option to reschedule or be refunded.
Marathon Inshore 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 Yellowtail, Snapper, Permit, Tarpon, Grouper, Barracuda, and Shark.
Your tour is guided by a licensed Captain in a modern open fishing style boat with a 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.
Booking with confidence on TripAdvisor, it makes this charter an easy, reliable and enjoyable decision. Reserve Today to get hooked up! 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.
Key West: Fun Full Day Beach Pass Watersports and Activities
Smathers Beach full day pass and activities. This is Key West’s best public. Jump on a paddle board, kayak or hobie cat & explore the Key West Atlantic coast. Sail on a Hobie cat in the crystal clear waters. Beach pass includes a choice of a parasailing ride or chair & umbrella. Enjoy a full day with this all inclusive activity package.
4 Hour Sunset Seasonal Tarpon Charter from Key West
On your 4-hour sunset tarpon charter, we’ll focus on targeting migrating tarpon during one of the most active feeding windows of the day. Sunset is prime time to hook into these powerful fish, and there’s often a chance to catch bonus dinner species along the way. This seasonal trip runs from April 20 to June 20 and offers a short but incredible window to connect with the fish of a lifetime.
We are especially passionate about tarpon fishing—chasing these giants is what we look forward to all year. With a limit of four anglers, you'll have the space, attention, and strategy you need to make every shot count. From dialing in your presentation to managing long, high-adrenaline fights, this trip is all about making the most of a brief and unforgettable season on the water.
Four Passenger Cart Rental
Our 4-passenger golf cart rentals are the perfect blend of convenience, fun, and flexibility for exploring Key West.
With a smaller footprint than larger carts, these vehicles are easy to maneuver through Old Town’s charming streets and tight parking areas, making them ideal for couples or small groups who want to move around the island quickly and effortlessly.
What truly sets Fun Rentals apart is our focus on quality equipment and local expertise. Our modern, street-legal carts are comfortable, reliable, and designed for smooth island cruising.
Our friendly team also provides insider tips on the best scenic routes, hidden local gems, and must-see attractions so you can make the most of your Key West adventure.
You’ll be able to cruise famous spots like Duval Street, visit the sunset celebration at Mallory Square, and stop for photos at the Southernmost Point Buoy — relaxed, all at your own pace!
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
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!
Exclusive Key Lime Pie Show and Tasting in Key West
A quick culinary adventure awaits at the Exclusive Key Lime Pie Show in the vibrant heart of Mallory Square. In just 30 minutes, discover the secrets to crafting the iconic Key lime pie, from mastering the graham cracker crust to achieving that perfect, creamy filling. After the lively demonstration, savor a slice of the world-famous pie, made without any green food coloring. Plus, take home the official recipe card to recreate this delicious treat at home, ensuring your taste of Key West lasts well beyond your visit.
Key West Craft Cocktail Experience
Explore the lively world of craft cocktails in a unique 1.5-hour session at Key West's oldest brick building. Get your hands on authentic bar tools to create two cocktails, while also sampling three others. Delight in tasty bites as you soak in tales of local legends like William Curry and the charming history that shaped this island paradise. With expert bartenders guiding you, this hands-on experience is perfect for anyone looking to mix it up while learning about Key West's vibrant past. Plus, take home some fun SWAG as a memento.
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!
Hire Photographer, Professional Photo Shoot - Key West
Professional photo shoot in unique Key West locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see undiscovered locations and get the best photo story from your Key West visit. We can tailor each photo shoot to meet your requirements; we can travel to your location or we can suggest a location for the photo shoot.
Our Photoshoots are ideal for any Tourists
- Solo Traveller
- Couples
- Groups
- Hen/Bachelorette & Stag/Bachelor Parties
- Families
- Secret proposal/Engagement
- Honeymoon
- Experienced Influencers and Models
- New Influencers and Models
What's Included:
A Private online viewing gallery
- 1 hour = 20 Final photos*
- 2 hours =30 Final photos*
- 3 hours =40 Final photos*
- 4 hours =50 Final photos*
* same set of images
- A unique location professional shoot experience
- DELIVERY - Up to 14 days after photoshoot.
What's Excluded:
- Transportation
- Entry fees
Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs
You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience its amazing architecture and historic sites as you learn the rich history, culture, and folklore of our beautiful island of Key West.
First-row, Historic, Cultural and Fun, the only VIP experience tour in Key West.