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
No similar experiences found
Viator
Day Sailing Adventure in the Florida Marine Sanctuary
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailboat rides feature the perfect blend of natural beauty, maritime history, and the thrill of the open sea. Don't forget your camera – this is a photo opportunity you won't want to miss! Book your spot now and get ready to create memories that will last a lifetime.
5.0(41)
3 Hours
Key West
- Free cancellation
From
$120
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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
No similar experiences found
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
1 Hour Key West Jet Ski Freestyle Adventure
Short on time and want to do your own thing? Our supervised Freestyle Adventure is perfect for you. Our guide will take you to a secluded area where you can let loose and get your jet ski on. This jet ski rental is a great way to let loose and get your adrenaline fixed, or you just relax and chill if you prefer. It’s completely up to you. Some people don’t care for structured, guided tours. That’s why we came up with this freestyle alternative. Book yours today!
5.0(22)
1 Hour
Key West
- Free cancellation
From
$165
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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
No similar experiences found
Viator
Florida Keys Sunset Cruise with Champagne Toast and Seafood
Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp (when in season), offering an authentic taste of the region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.
5.0(16)
2 Hours
Key West
- Free cancellation
- New
- Likely to sell out
From
$69
No similar experiences found
Viator
Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida
Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks such as Boot Key Harbor, the Atlantic Ocean, and the historic Seven Mile Bridge. Relax on deck and enjoy the changing colors of the sky while sipping a complimentary champagne toast. The catamaran offers plenty of seating, shaded areas, an onboard restroom, and a cooler stocked with ice, water, and soda. This tour provides a laid-back and memorable way to experience the Keys at golden hour—perfect for couples, families, and anyone who wants to unwind on the water.
5.0(12)
2 Hours
Key West
- Free cancellation
- New
- Likely to sell out
From
$102
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Viator
Key West Nighttime Full Moon Sail
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moon comes up over Key West, enjoy star gazing opportunities and a moonlit sky as the boat glides through the majestic waters at night.
5.0(10)
1h 30m
Key West
- Free cancellation
- Likely to sell out
From
$84
No similar experiences found
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
No similar experiences found
Viator
Cruisin Tikis Marathon - Sunset Tiki Cruise
Ready for the most beautiful 2 hours of your Florida Keys vacation? Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into the beautiful water of the Florida Keys. Our 2-Hour Sunset Tiki Cruise transforms the spectacular Keys sunset into a private, moving masterpiece just for you. The Magic of the Sunset Cruise: Front-Row Seat to Nature’s Show: Glide across the tranquil, crystal-blue waters as the sky ignites in a breathtaking palette of reds, oranges, and pinks. You'll have the best, unobstructed view of the legendary Keys sunset from the comfort of your floating tiki bar. A Toast to Paradise: Whether you're celebrating a special occasion or simply savoring a perfect day, the sunset hour is magical. Bring your favorite beverages to toast the end of a perfect day as the stars begin to appear over the horizon. Secure your spot now and create a memory that will glow long after the sun goes down!
5.0(7)
2 Hours
Key West
- Free cancellation
- Special offer
- New
From
$89
No similar experiences found
Viator
Hula Hank's Key West Tipsy Tiki Sunset Cruise
Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key West sunset - hues of orange, pink and purple. Sip on ice-cold beverages prepared by your friendly crew while the warm sea breeze carries the sounds of island music and laughter. The atmosphere is relaxed and festive, perfect for making new friends or sharing moments with loved ones. Expect a laid-back and enjoyable trip while unwinding with a refreshing beverage from the bar. As the last sliver of sun disappears below the water, watch for the green flash, an enchanting touch of magic. Sail back to Key West Harbor under the star-filled sky, creating a Key West memory to last a lifetime.
5.0(6)
1h 30m
Key West
- Free cancellation
From
$80
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Viator
Key West Christmas Cruise with Live Band and Drinks
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. Enjoy a festive hot cocoa and holiday treats as we glide along with water for a fun night in Key West. Our beautiful 105-foot Schooner America 2.0 in full holiday decor that's sure to get you into the Christmas spirit in Key West harbor.
5.0(5)
1h 30m
Key West
- Free cancellation
- Likely to sell out
From
$98
No similar experiences found
Viator
Key West Night Cruise aboard Schooner America 2.0
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy unobstructed views of the sweeping night sky and a fun adventure in Key West at night. Please note there are different options for this experience. Select departures will have live narration from a seasoned local astronomer, or a local guide sharing nautical superstitions with Key West's most famous ghost stores. Select options accordingly at check-out.
5.0(5)
1h 45m
Key West
- Free cancellation
- Likely to sell out
From
$84
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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
No similar experiences found
Viator
Marathon: Local Sandbar Escape
Our US Coast Guard licensed captains have decades of combined excursion experience in the Middle Keys and look forward to sharing our lovely paradise with you! Your captain will provide all the tips to have you exploring our local sea-life in no time. We hold ourselves to a high standard and run a quality operation. With your enjoyment in mind, our boats are clean and comfortable offering multiple seating options, and maintained regularly. After your 2 hour excursion, you’ll fall in love with the Keys! Florida Mom owned, voted Best in Marathon 2023, 2024
5.0(4)
2 Hours
Key West
- Free cancellation
From
$119
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Viator
Florida Keys Tiki Boat Tour Adventure
Embark on a lively 1.5-hour Tiki Fun Cruise through the stunning Florida Keys. Glide over crystal-clear waters on an authentic tiki bar boat, where you can savor your favorite drinks while soaking up the sun. Keep your eyes peeled for dolphins, sea turtles, and vibrant seabirds as your knowledgeable captain shares insider secrets and local history of the Keys. Choose between a picturesque scenic harbor cruise or a refreshing swim stop at a beautiful sandy beach. This tour promises to be a memorable highlight of your Florida adventure. - 1.5-hour cruise on a unique tiki bar boat - Spot dolphins, turtles, and seabirds in their natural habitat - Learn local history and fun facts from your captain - Choose between a scenic cruise or a swim stop at the beach
5.0(4)
2 Hours
Key West
- Free cancellation
- Special offer
- New
From
$76
No similar experiences found
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
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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
No similar experiences found
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
No similar experiences found
Viator
Morning Mimosa and Swim 2hr Luxury Cruise in Marathon FL
Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon. Enjoy a complimentary morning mimosa as the crew guides you along scenic coastlines with views of the Atlantic Ocean, Boot Key, and the iconic Seven Mile Bridge. Take a refreshing swim in calm, shallow waters and explore the sandy bottom for shells and sea life. With plenty of space on board, comfortable seating, and friendly local crew, this tour offers a peaceful and memorable way to experience the beauty of the Florida Keys.
5.0(3)
2 Hours
Key West
- Free cancellation
- New
From
$89
No similar experiences found
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
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
