Key West
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Viator
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.
5.0(46)
3 Hours
Key West
- Free cancellation
- Private tour
From
$550
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Viator
Florida Keys Backcountry Eco Tour from Big Pine Key
This 2 hour Eco Tour will take you by boat to explore the Backcountry of the Florida Keys. We will cruise through the mangrove islands that make up the Backcountry and Great White Heron National Wildlife Refuge. We will slow down and look for marine life and birdlife. Maybe see a turtle or dolphin. We will take you through "Skinny Water" and look for starfish, rays and sharks. It's a fun adventure not to be missed when visiting the Keys.
5.0(30)
2 Hours
Key West
- Free cancellation
- Private tour
From
$450
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Viator
Private Boat Tour to Sand Bar Snorkel Dolphins and Sunset
Join me, a true seventh-generation local captain for a personalized Key West adventure on my private boat. Spend the day exploring the stunning turquoise waters and hidden islands of the Florida Keys, with opportunities to snorkel, search for dolphins, visit a sandbar, enjoy light fishing, or simply relax and take in one of Key West’s world-famous sunsets. Every trip is fully private and tailored to what you want to experience — whether it’s adventure, leisure, or a bit of both. Departing conveniently from Garrison Bight Marina, your journey promises incredible views, local insight, and unforgettable memories on the water.
5.0(27)
3h 30m
Key West
- Free cancellation
- Private tour
From
$600
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Viator
Boat Excursion in Florida Keys with Snorkeling Equipment
Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the Lower Keys really well. So there are a few different areas to choose from on where to go and we can decide based on weather, wind, etc. There is the option to bring up to 2 kayaks ($25 rental fee per kayak). Snorkel equipment available (just let us know in advance sizes). The guide would be glad to hop in and point things out just let him know ahead of time. Possibility of seeing dolphins. We love the ocean and have a passion for being on or under the water! Also we are kid friendly!
5.0(22)
4 Hours
Key West
- Free cancellation
- Private tour
From
$700
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Viator
Private Boat Tour of Flagler's Famous Bridges from Big Pine Key
This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll cruise up the bay side and back down the ocean side (or vice versa). Learn the history of the bridges and the Flagler Railway, and see mangroves and beaches. A great way to see the keys!
5.0(18)
1 Hour
Key West
- Free cancellation
- Private tour
From
$400
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Viator
Key West Historic Private Food Tour with 5 Authentic Tastings
Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings that celebrate the island’s unique mix of Cuban, Caribbean, and Floridian influences. Start with a refreshing iced coffee before biting into golden, crispy conch fritters—a true island classic. Savor authentic Cuban cuisine that reflects Key West’s cultural heritage, then indulge in rich chocolate-covered Key lime pie, the city’s most famous dessert. Along the way, your guide will share stories of pirates, poets, and island life, bringing the history and charm of Key West to life. To end, you’ll taste our exclusive Secret Dish, a surprise that makes the experience truly unforgettable. This is Key West beyond the postcard—an authentic taste of its food, culture, and soul. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience.
5.0(15)
2h 30m
Key West
- Free cancellation
- Private tour
From
$370
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Viator
PRIVATE Key West Haunted History Walking Tour
Walk through Old Town Key West with a long-time local, hear the haunted history of Key West, her beautiful historic mansions, and visit a haunted bar or two. 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! We walk past at least 5 haunted mansions and visit two haunted bars. Total distance is around 1 mile. Libations for purchase are available along the way, if you so choose. The best part about your own private tour is you can ask questions and customize the kinds of stories you want to hear! Feel free to include notes in your booking about: - what you want to know about the spooky side of Key West - if you're celebrating an event - mobility challenges or other needs we can accommodate - if you have kids, their level of 'spooky'
5.0(10)
1h 30m - 2 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$138
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Viator
4 hours Private Fishing Charters in Key West 40 Ft Irish Cowboy
Get ready for an exhilarating adventure on the vibrant waters of Key West with our private deep sea fishing charters. Led by the skilled and experienced Captain, our team is dedicated to making your fishing trip unforgettable. Reel in the fight of a lifetime as you battle magnificent mahi, king mackerel, sailfish, and more. Our knowledgeable captain and mate will guide you to the sharky hotspots and employ various techniques, including trolling and bottom fishing, to maximize your chances of landing a trophy catch. We believe in providing personalized service. Whether you're a seasoned angler or a curious first-timer, we'll tailor the experience to your skill level and preferences. We offer well-equipped vessels, clean facilities, and essential safety gear for a smooth journey
5.0(10)
4 Hours
Key West
- Free cancellation
- Private tour
From
$950
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Viator
Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY
Experience an Unforgettable Fishing Adventure in Key West! Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater to both seasoned anglers and first-timers, ensuring an unforgettable experience. Reel in magnificent mahi, wahoo, sailfish, and more. Our knowledgeable crew will guide you to prime fishing spots, employing techniques like trolling, reef, or wreck fishing and many more to maximize your chances of landing a trophy catch. Choose from flexible charter options: 1/2-day, 3/4-day, full-day, or extended 10-12 hour trips tailored to your preferences. Our 36-foot Hatteras "Cowboy" offers comfort and safety with clean facilities, restrooms, , a flybridge, and state-of-the-art equipment. Book now and discover why our private charters are the ultimate choice for a thrilling day on the water in Key West.
5.0(5)
4 Hours - 12 Hours
Key West
- Free cancellation
- Private tour
From
$850
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Viator
Private Afternoon Snorkel with Sunset Sail in Key West
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's amazing natural wildlife with up to five others, before sailing back to shore at sunset.
5.0(4)
4 Hours
Key West
- Free cancellation
- Private tour
From
$995
No similar experiences found
Viator
Escape Rooms Outdoors on the Waters of Key West!
Choose your adventure! Castaway, Mermaid, or Conch Quest !! Each charter is four (4) hours, with the escape game being one hour of the adventure (Conch Quest adventure is several hours). You will board a large, comfortable deck boat with an experienced captain who will take you to a few beautiful locations for snorkeling, playing the escape adventure, and relaxing and eating/drinking for the remaining time. We provide all safety gear, snorkel gear, ice, bottled water. You provide your own food/drink/towels. Book today!
5.0(4)
4 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$500
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Viator
Half Day Luxury Boat Tour in Key West with Snorkeling
Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring with stops like Fort Zachary Taylor Historic State Park, U.S. Coast Guard Cutter Ingham Maritime Museum, Smathers Beach, Southernmost Point of your list.
5.0(3)
4 Hours
Key West
- Free cancellation
- Private tour
From
$700
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Viator
Florida Keys Tour and Private Transportation service
Your tour/shuttle can go anywhere between For Lauderdale Florida and Key West! As you check out you'll have the chance to let us know where you're hoping to travel to. We'll come and pick you up and drop you off wherever is convenient for you. Reach out to us if you want us to supply a cooler with any beverages on your tour. Must have at least one adult in your party. The van holds a Maximum of 14 passenger.( Price includes up to 14 Passengers)
5.0(2)
10 Hours - 12 Hours
Key West
- Free cancellation
- Private tour
From
$985
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Viator
Private Sandbar Charter & Island Escape in Key West
Explore the crystal-clear waters and pristine sandbar islands that surround the Florida Keys. This private sandbar charter is fully customizable—whether you’re looking to relax with a drink in hand, explore the local marine sanctuary, or simply enjoy a laid-back day on the water. Your captain will tailor the experience to your preferences, taking you to the best sandbar spots and providing everything you need for a carefree day in paradise. Enjoy sunshine, calm waters, and unforgettable views of Key West’s natural beauty. This is the ultimate way to experience the islands—your day, your way, in the heart of the Florida Keys.
5.0(2)
4 Hours
Key West
- Free cancellation
- Private tour
From
$800
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Viator
Private Guided Mangrove Eco-Tour Adventure
Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty of the Florida Keys. Paddle through tranquil mangroves where your expert guide highlights local wildlife and ecological wonders, from tropical bird habitats to vibrant sea turtles. This eco-friendly adventure is suitable for all skill levels, ensuring a relaxing time as you navigate the peaceful waterways. Discover hidden gems and soak in the lush surroundings, all while enjoying small group sizes for a personalized experience.
5.0(1)
2 Hours
Key West
- Free cancellation
- Private tour
From
$395
No similar experiences found
Viator
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.
5.0(1)
2 Hours
Key West
- Free cancellation
- Private tour
From
$750
No similar experiences found
Viator
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.
5.0(1)
4 Hours - 8 Hours
Key West
- Free cancellation
- Private tour
From
$725
No similar experiences found
Viator
Experience Florida Keys Boat Charter Private Tour
Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while soaking in the sun and taking in stunning views of luxurious homes and coastal landscapes. Keep your eyes peeled for dolphins, sea turtles, and tropical seabirds as you glide over the crystal-clear waters. You can choose between a scenic harbor cruise or an island swim stop at a sandy beach for a refreshing dip in the turquoise sea. This is the perfect way to create unforgettable memories in paradise. - Enjoy a leisurely 1.5-hour cruise on a tiki bar boat - Spot local wildlife, including dolphins and sea turtles - Customize your cruise with a scenic harbor tour or beach swim - Knowledgeable Captain shares local history and fun facts
5.0(1)
1h 30m
Key West
- Free cancellation
- Private tour
- New
From
$460
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Viator
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.
5.0(1)
2 Hours
Key West
- Free cancellation
- Private tour
From
$392
No similar experiences found
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 Looe Key Snorkel from Big Pine Key
Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef system after the Great Barrier Reef in Australia, and the Palancar Reef in Mexico and Belize. It is a special place for snorkeling.
5.0(442)
3 Hours
Key West
- Free cancellation
- Private tour
From
$599
No similar experiences found
Viator
Custom Charters with a Local Captain
These Tours are unique because they are offered by a seventh generation local who knows the waters and can take you to places other people can’t. This completely custom and private tour so start Band end times are charla e upon guests request. You will have a great day on the water looking at dolphins snorkeling going to sandbars swimming and taking in the beautiful scenery.
5.0(48)
3h 30m
Key West
- Free cancellation
- Private tour
From
$250
No similar experiences found
Viator
Marathon to Key West Private Tour of Florida Keys
Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.
5.0(27)
8 Hours
Key West
- Free cancellation
- Private tour
From
$137
No similar experiences found
Viator
Private Sunset Cruise around Key West
Visit Stockislandboatcharters.com for alternate availabilities and pricing. Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your guide will be talking you through many points of interest around the island. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, your captain will find a quiet and private spot to watch the sun drop into the water uninterrupted by other boats, people, or land!
5.0(66)
2 Hours
Key West
- Free cancellation
- Private tour
- Likely to sell out
From
$400
No similar experiences found
