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.
Sandbar Snorkel Combo Adventure
This combo tour offers two experiences in one: a peaceful sandbar visit and an exciting snorkeling session. Unlike standard trips, you’ll enjoy a well-planned itinerary that maximizes your time on the water, with expert guidance and access to prime locations.
Snorkeling and Catamaran Adventure in Key West
Sail from Key West Bight aboard Papa’s Cat, a 48-ft catamaran inspired by Hemingway’s island spirit. Dive vibrant reefs, drift over sugar-white sandbars, and sip fresh coconuts as you soak up
the sun. With snorkel gear, towels, sunscreen, Cuban sliders, and Key West pink shrimp included, this private four-hour charter for up to 10 guests captures the easygoing magic of Key West—equal parts exploration and relaxation.
Key West Spirits and Haunted Pub Crawl
Experience Key West’s top-rated haunted pub crawl, where chilling ghost stories, historic bars, and island cocktails come together for a night of spooky fun in the heart of Old Town. Led by passionate local guides who know the city by heart, you’ll uncover the dark history, haunted legends, and hidden secrets behind some of Key West’s most iconic locations. Along the way, visit legendary stops like Sunset Pier, First Flight Island Restaurant & Brewery, Curry Mansion Inn, Hard Rock Cafe Key West, The Oldest House Museum & Garden, and more haunted hotspots filled with tales of shipwrecks, restless spirits, and mysterious encounters. With eerie streets, unforgettable storytelling, and plenty of chances to grab a drink along the way, this ghostly adventure is the perfect mix of history, mystery, and nightlife!
PADI Refresher Course
We make your first dive unforgettable with small groups, expert PADI instructors, and the best gear on the market - SCUBAPRO. We start you off in the pool to help build confidence and to shake the rust off. Then you will head to our air conditioned facility in downtown Key West. After a quick check-in process you’ll board our custom built dive boat, The Phoenix, conveniently docked across the street behind the Hyatt Centric Hotel. Safe, fun, eco-friendly, and outfitted with premium equipment, we can’t wait to get you back in the water!
Key West Private Wildlife Refuge Eco Boat Tour
This private eco boat tour focuses on the Key West National Wildlife Refuge and its mangroves, islands, flats, and coastal habitats. Your group can prioritize wildlife viewing, photography, snorkeling, swimming, or relaxed exploration. The flexible itinerary responds to current conditions and refuge protections, giving guests a private and respectful way to experience Key West’s backcountry environment.
Dolphin Watch and Snorkel Tour in Key West
Explore the vibrant waters of Key West on this exciting Dolphin Watch & Snorkel Tour. Enjoy a family-friendly adventure as you snorkel in the beautiful backcountry waters, home to an array of marine life including tropical fish, sea turtles, and more. Spot dolphins in their natural habitat and soak in the stunning surroundings aboard a spacious catamaran. With expert guidance and all snorkeling gear provided, it's perfect for both beginners and experienced snorkelers. Relax afterwards with snacks and refreshing drinks as you share stories of the day’s adventures.
- Duration of the tour is 3.5 hours, offering plenty of time for exploration.
- All snorkeling equipment is included, with expert instruction available.
- Enjoy complimentary snacks and drinks, including beer and soft drinks.
- Limited to 36 guests for a comfortable and spacious experience.
Stock Island Booze Cruise
Climb aboard and let the tropical breeze set the tone as we cruise past working marinas, colorful houseboats, and mangrove-lined shores where dolphins often play in our wake. With island tunes flowing and an ice-cold drink in hand, you’ll drift effortlessly into vacation mode.
Our first stop: Hogfish Bar & Grill, a local legend tucked into the heart of the docks. Here, fishermen unload their daily catch and the vibe is pure Old Key West. Sink your teeth into their famous fresh hogfish sandwich or sip a cocktail right on the waterfront.
Next, we glide over to Bad Boy Taqueria, a fun and funky stop known for bold flavors, creative tacos, and the kind of energy that makes you want to stay all afternoon. Grab a bite, grab a drink, and soak in the local charm.
Then it’s off to Hurricane Hole Marina, a favorite for both locals and salty sea captains. With strong drinks, great music, and unbeatable views of the harbor, it’s the perfect place to relax before we head back out on the water.
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.
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
Key West Private Patch Reef Fishing Charter for Families
This private patch reef charter offers accessible Key West fishing without requiring a long offshore run. The trip can accommodate up to six passengers, with a maximum of three people fishing simultaneously. Captain Dustin’s charter license covers fishing guests; if another captain operates the trip, guests who will fish must obtain the required temporary Florida saltwater licenses.
Private Morning Tiki Boat Eco Cruise in Key West
You will be cruising the near shore waters of Key West and the Florida Keys on a custom Tiki Bar Boat. Your US Coast Guard Certified Captain is extremely knowledgeable and will point out all the amazing sights. Be sure to bring a camera and a polarized lens for the best photos.
Private Customizable Charter in Marathon Florida
This snorkeling adventure goes beyond the ordinary by offering crystal-clear waters, vibrant coral reefs, and an incredible variety of marine life—all in a serene, picturesque setting. Unlike standard tours, we prioritize your safety and comfort with a dedicated crew, allowing you to fully relax and enjoy the experience. It’s not just a snorkeling trip—it’s an immersive journey into the beauty of the ocean, designed for both beginners and seasoned explorers.
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.
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.
Intimate Key West Elopement Experience
Escape to paradise and say “I do” with a romantic one-hour Key West elopement. Enjoy a personalized ceremony led by a local officiant at a picturesque beach or waterfront setting, followed by professional photography to capture your vows and relaxed portraits. You’ll receive high-resolution digital images in an online gallery for easy sharing. Book your stress-free Key West elopement and celebrate your love in paradise!
Key West: Smathers Beach & activities with a Sunset Catamaran & Open Bar
Fun in the sun when you make it over to Smathers Beachand have the best day with unlimited use of water activities. Go kayaking, paddle boarding, sailing or just seat in your beach chair and umbrella and enjoy the sun. Make sure to be at the check in for you sunset cruise with live music and open bar no later than 4:15 check in for a 5pm departure. On the 2 hour Sunset cruise you will have an open well bar which includes rum-runners, margaritas, mixed drinks, draft beer, wine, champagne & soft drinks. We will service finger food appetizers like Jamaican jerk chicken sliders on Hawaiian rolls, BBQ meatballs, veggie trays, cheese & cracker trays, Pita & hummus.
Marathon Backcountry Fishing Charter
Experience the true beauty of the Florida Keys backcountry, gorgeous shallow flats, and abundance of fish. Marathon the hub for fishing in the Keys, great beaches, shopping, and fantastic food. Knowing like the beautiful scenery, while experiencing the thrill of a chance to catch species such as Bonefish, Tarpon, Snook and the hard fighting Permit.
Your tour is guided by a licensed Captain in a modern skiff or also called a flats boat. 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.
Full Day Backcountry Fishing Charter in Key West
Our full-day backcountry charter gives you the time and range to dive deeper into the fishing opportunities surrounding Key West. With 8 hours on the water, we can go beyond the usual grounds—working the flats, channels, and mangrove edges at your pace, with the flexibility to follow the bite wherever it’s best. Depending on conditions, we may even venture west toward the remote Marquesas Keys, known for their rich marine life and pristine beauty.
Our captain is a lifelong angler and Army veteran who brings both local knowledge and a steady, thoughtful approach. There’s no set route or rigid schedule—just a focus on giving you the best possible day on the water. With a max of four guests, you’ll fish comfortably and get personalized insight into the backcountry’s changing tides and seasonal patterns. It’s a full day built for anglers who want to go further and get more from their time on the water.
Key West Sportfishing Experience 4 Hours 47 Hatteras-Sanctuary
Private Offshore Fishing on Sanctuary – 47 ft Hatteras
Experience the thrill of offshore fishing in Key West aboard Sanctuary, our 47 ft Hatteras. Led by an expert Captain and mate, we’ll take you to the best deep-sea fishing spots for an unforgettable adventure.
Target Top Game Fish: Reel in mahi-mahi, king mackerel, sailfish, tuna, and more using trolling and bottom fishing techniques.
Tailored to You: Whether you're a seasoned angler or a beginner, we customize each trip to match your skill level. Choose from half-day (4 hours), full-day, or multi-day charters.
Comfort & Safety: Enjoy spacious decks, premium gear, a clean restroom, and all essential safety equipment for a smooth trip.
Book your private offshore fishing adventure today!
Key West Private Bachelorette Yacht Party Cruise
This private Key West bachelorette boat charter is reserved for your group rather than shared with strangers. Celebrate aboard a Jeanneau NC 895 Weekender and tailor the outing around sandbar time, snorkeling, wildlife viewing, waterfront cruising, or sunset views when conditions permit. It combines a private yacht-party atmosphere with a flexible itinerary and a captain responsible for safe navigation.
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.
Private Proposal and Engagement Shoot in Key West
We take the time to review YOUR vision for this special moment in life via a conference call - we offer suggestions and then send a full confirmation with map or diagram and all aspects to make this a perfect surprise to the love of your life and your lifetime partner.
Key West Airport (EYW) to Key West - Arrival Private Transfer
Book your Private Arrival Transfer from Key West Int Airport (EYW) to Key West hotels.
Don't go through all the hassle of waiting in a long taxi or shared shuttles queues 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
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers