Key West
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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.
5.0(1)
4 Hours
Key West
- Free cancellation
- Private tour
From
$1,100
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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.
5.0(1)
8 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$1,595
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Viator
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.
5.0(1)
1 Day
Key West
- Free cancellation
From
$150
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Viator
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.
5.0(1)
2 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$350
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Viator
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.
5.0(1)
8 Hours
Key West
- Free cancellation
From
$100
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Viator
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
5.0(1)
4 Hours
Key West
- Free cancellation
- Private tour
From
$875
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Viator
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.
5.0(1)
4 Hours
Key West
- Free cancellation
- New
From
$162
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Viator
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!
5.0(1)
1 Day - 7 Days
Key West
- Free cancellation
- New
From
$165
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Viator
2 HR Key West Clear Kayak Rental – Discover Mangroves & Wildlife!
Enjoy the freedom and flexibility we offer—whether you want to paddle for just an hour or spend a full four hours exploring, you can do it all at your own pace. Our launch site gives you direct access to some of Key West’s most stunning and secluded mangrove tunnels, so you're in the heart of the adventure within minutes. No guided schedule, no rushing—just you, the water, and the wildlife. With high-quality gear, easy-to-follow route maps, and a laid-back local vibe, we make it simple to experience the best of Key West’s natural beauty, on your own terms.
5.0(1)
2 Hours
Key West
- Free cancellation
From
$50
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Viator
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!
5.0(1)
1 Day - 7 Days
Key West
- Free cancellation
- New
From
$185
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Viator
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.
5.0(1)
4 Hours
Key West
- Free cancellation
- Private tour
From
$800
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Viator
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.
5.0(70)
2h 30m
Key West
- Free cancellation
- Private tour
From
$229
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Viator
Private Fishing Charter from Ramrod Key
you'll be able to fish the Atlantic side of the Florida Keys and the Gulf side in the same outing if you so desire.
5.0(45)
4 Hours
Key West
- Free cancellation
- Private tour
From
$500
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Viator
Key West: Sunset Sail + Reef Snorkel & Sandbar
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows you the best spots, ensuring you and your loved ones get the best experience on your tour. • Small Groups With a max group size of 24 guests and the warm calm weather of summer, you will see what makes an Honest Eco tour great for your group. Who is this trip for? We are a small family owned business, started by a biologist to offer authentic experiences that we would want to book. • We cater to Couples and Families who want a nature experience and would prefer to avoid the packed party boats. What is the Boat? The boat is a wide open 42' sailing catamaran that immerses you in the nature experience. It has a head on board, and we offer Fresh Organic Fruit and Filtered Water, Safety equipment and really good snorkeling gear.
5.0(35)
4h 30m
Key West
- Free cancellation
- Likely to sell out
From
$143
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Viator
Private boat Charter key west, Dolphin tour, Snorkeling & Sandbar
Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches only accessible by boat, with a flexible itinerary customized just for you. • Watch wild dolphins in their natural habitat • Private eco-friendly tour, just for your group • Cruise Key West’s beautiful backcountry waters • Flexible departure times to fit your schedule • Learn about marine life from a local guide
5.0(26)
3 Hours
Key West
- Free cancellation
- Private tour
From
$792
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Viator
Marathon FL Sandbar Cruise & Sightseeing Adventure
Discover the charm of Marathon, FL, with a delightful Sandbar Experience and Sightseeing Cruise. Enjoy a 4-hour adventure exploring the local scenery on a comfortable boat, complete with unique views of the island. Spend a relaxing day at the sandbar, where you can swim in the crystal-clear waters, or opt for kayaking and paddleboarding to enhance your aquatic adventure. Light snacks, drinks, and friendly crew members ensure a fun-filled day for all ages. - 4-hour tour ideal for families and all ages - Scenic boat ride to the sandbar with opportunities for swimming and water sports - Light snacks and drinks provided; guests can bring their own food (no glass or hard alcohol) - Relaxed atmosphere with ample time to enjoy the beautiful waters and surroundings
4.9(95)
4 Hours
Key West
- Free cancellation
From
$114
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Viator
Guided Bike Tour of Old Town Key West
Ride with Key Lime Bike Tours for a truly unique and unforgettable Key West experience! See the islands top attractions with your own friendly knowledgable guide! Cruise Old Town, visit iconic landmarks, and hear stories about some of the colorful characters that have called Key West home. You will get the best Key West photos and see more in two hours then most visitors see their entire trip to Key West. Ride a bike from the Gulf to the Atlantic and see the Southernmost from Coast to Coast! Voted Key Wests #1 Land Excursion 10 years in a row! ALL OF OUR AMAZING RIDERS ALSO RECEIVE DISCOUNTS ON BIKE RENTALS AND OUR AWESOME MERCH! Cold bottled water and Key Lime pie included!
4.9(2705)
2 Hours
Key West
- Free cancellation
From
$59
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Viator
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!
4.9(37)
3h 30m
Key West
- Free cancellation
- Private tour
From
$600
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Viator
KeyWest Half-Day Inshore Fishing Private Charter
These trips are very customizable trips from all skill levels of charter fishing to just kicking it at the sandbar we are here to make this the best part of your vacation.
4.9(68)
4 Hours
Key West
- Free cancellation
- Private tour
From
$750
No similar experiences found
Viator
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling
Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and Principal Engineer known for his high-efficiency catamaran designs, to build the perfect boat for our trips from scratch. Our amazing crew are closely trained by our Honest Eco Biologists. Crew training starts on land with research and mission alignment before moving onto the water where we hone our seamanship skills and work to become as effective as possible at delivering on our Purpose. We Work to Spread the Value of Wildlife Conservation “People Protect What They Love.” Jacques Costeau said it, and it inspires us at Honest Eco as we work to help people discover and fall in love with the environment we are all part of. We are continuously learning and pushing ourselves to be as environmentally responsible as possible.
4.9(555)
4 Hours
Key West
- Free cancellation
From
$143
No similar experiences found
Viator
Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail
Danger Charters is the only tour operator in Key West offering sailing excursions on a historic schooner into the remote backcountry of the National Wildlife Refuge. Our trips are truly small-group, with a max of around 20 guests, so you'll never feel crowded—whether you're snorkeling, kayaking, or relaxing on deck. On the Premium Day Trip, we often stop at a shallow sandbar, a guest favorite for swimming, wading, or just enjoying the view! What really sets us apart is our crew. They're passionate about what they do, and it shows in the way they lead each activity, share local history, and give fun, informative eco talks. Whether you're brand new to snorkeling or a seasoned paddler, the crew offers guidance, support, and an easygoing atmosphere that makes everyone feel welcome. This trip combines adventure, education, and laid-back sailing in one of the most beautiful and untouched parts of the Florida Keys.
4.9(813)
6h 30m
Key West
- Free cancellation
- Likely to sell out
From
$159
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Viator
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Included in the tour price is bottomless house champagne Chandon Brut, 8 premium red and white still wines, ice-cold beers & White Claws, and a champagne-inspired Gourmet Cheese Buffet (naturally gluten free) that includes 4 incredible international cheeses, paired plump berry tray, local smoked fish dip, crunchy crisps and fresh-baked crusty bread. Two other Moët & Chandon champagnes are available for additional purchase - both at wholesale price - only for onboard guests. Key West is famous for its tropical sunset, and there’s no better way to watch it than on this famous Sunset & Moët Cruise. This public trip is always limited to 14 adult passengers on a 28 person sailing catamaran, for guests comfort and quality control. And NO kids!
4.9(987)
2 Hours
Key West
- Likely to sell out
From
$109
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Viator
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.
4.9(18)
2 Hours
Key West
- Free cancellation
From
$75
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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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