Key West
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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
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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
Champagne Dolphin Sail and Reef Snorkel
Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the wild dolphins that live, feed and breed right along the south side of Key West. Get that yacht feeling with Champagne Service from your professional crew. Tickets are fully refundable if canceled outside of two weeks in advance!
5.0(9)
3 Hours
Key West
- Likely to sell out
From
$109
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Viator
Florida Keys Kayak And Paddleboard Rentals
Explore the stunning waterways of the Florida Keys with our kayak and stand-up paddleboard rentals. Perfect for all ages and skill levels, this self-guided adventure allows you to navigate through beautiful mangrove tunnels and trails at your own pace. Enjoy a 2-hour rental with the option to extend and receive all necessary safety equipment, paddle instruction, and a satellite view map of the area. - Choose from single kayaks, tandem kayaks, or paddleboards - Discover the unique ecosystem of the Florida Keys - Perfect for both beginners and experienced paddlers - All rentals include safety equipment and instructional guidance
5.0(8)
2 Hours
Key West
- Free cancellation
From
$30
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Viator
Private Fishing Charter Florida Keys
Great for families. Customizable. Not a crusty old fishing charter by any means! Lots of sea life in the Florida keys! We can pull stone crab traps (Oct15-May 1st). Or get in and go for a swim or stop in at a sandbar! Captain has almost 20 years fishing experience. Take your catch to a restaurant to be cooked! Snorkel gear is available. Lobster diving charters are available in season (Aug 6-march 31). Pets are welcome
5.0(8)
4 Hours
Key West
- Free cancellation
- Private tour
From
$800
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Viator
America's Most Haunted Firehouse
This is your chance to go beyond the ghost stories and become the investigator in a place where the past refuses to rest. Exclusive inside access after hours. More than a ghost tour - its an experience. Tickets benefit local non-profits. Locally owned and operated by the Sloan Family.
5.0(8)
2 Hours
Key West
- Free cancellation
- Skip the line
From
$95
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
Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)
THE ONLY 2 DESTINATION TRIP IN MARATHON. Snorkel at the iconic Sombrero Reef and relax at the secluded Molasses Key Sandbar, perfect for a day of marine exploration. This 3.5-hour tour invites you to discover the vibrant underwater world of the 3rd largest barrier reef, where you can swim among tropical fish and coral. Enjoy the convenience of snorkeling gear, a floating mat, and a power catamaran led by a licensed captain. Cooler and ice are provided for your refreshments, ensuring a comfortable outing on the water. - Explore the renowned Sombrero Reef, teeming with marine life - Unwind at the exclusive Molasses Key Sandbar, away from crowds - Includes snorkeling gear and a power catamaran with a licensed captain - Convenient cooler and ice provided for your snacks and drinks
5.0(5)
3h 30m
Key West
- Free cancellation
- New
From
$154
No similar experiences found
Viator
Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour
Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll through the narrow, historic streets, you'll hear chilling tales of ghostly encounters, from restless spirits who never left to eerie legends passed down through generations. We’ll pass by the famous haunted landmarks, including the Key West Cemetery, where some say the dead still walk at night, and the eerie corners of Old Town, known for their strange, unexplainable occurrences. With the breeze in your hair and the moonlight casting long shadows, prepare for a spine-tingling ride into the heart of Key West’s most mysterious and supernatural stories. Buckle up, it's going to be a night you won't forget!
5.0(5)
1h 30m
Key West
- Free cancellation
From
$180
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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
Cudjoe Key, Florida Boat Rental Services
Enjoy the waters of the Florida Keys, don't have experience on the waters around Cudjoe Key? We have separate colored tracks to spots on the water on the 9" GPS.
5.0(5)
1 Day - 30 Days
Key West
- Free cancellation
From
$525
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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
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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
Backcountry Half Day Fishing Key West
Get out on the water and experience what Key West has to offer away from the bars. Beautiful waters in the backcountry, many types of fish, wildlife, and lasting memories. Shallow water fishing won't get you seasick!
5.0(4)
4 Hours
Key West
- Free cancellation
- Private tour
From
$750
No similar experiences found
Viator
Private Vacation Photoshoot with Photographer in Key West
⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Key West, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results
5.0(4)
1 Hour
Key West
- Free cancellation
- Private tour
From
$164
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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
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
Six Fins Key West Sandbar Charter – Swim, Snorkel & Island Escape
Discover the “backyard” of Key West locals with our Secret Sandbars Charter—hidden gems few visitors ever see. Unlike crowded party boats, this is your private slice of paradise. Imagine stepping off your boat into ankle-deep water, surrounded by endless blue sky and shimmering ocean, with no other boats in sight. Explore uninhabited islands, search for starfish and conch in the tide pools, or relax on a floating mat as the captain takes care of everything. This isn’t just a boat ride—it’s the ultimate Key West daydream, brought to life.
5.0(3)
4 Hours
Key West
- Free cancellation
- Private tour
From
$1,195
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Viator
Sandbar Excursions with Snorkeling and Sunset Cruises in Key West
Explore the beautiful waters of Key West with us, where the adventure includes snorkeling in crystal blue waters, lounging on secluded beaches, and witnessing stunning sunsets. This intimate charter accommodates up to 6 guests, ensuring a personalized experience. Choose from hourly, half-day, or full-day trips to tailor your Florida Keys getaway. Unwind and create unforgettable memories in paradise with a guided tour that showcases the essence of the Keys. - Snorkel in the clear waters of Key West with small group settings - Relax on secluded beaches away from the crowds - Enjoy breathtaking sunsets on the water - Flexible trip duration options: hourly, half-day, or full-day
5.0(3)
4 Hours
Key West
- Free cancellation
- Private tour
- New
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
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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
No similar experiences found
Viator
Key West Center Console Boat Rental With Sound and Seat Upgrade
We are Key West's largest boat rental service and have been helping travelers explore our local waterways for over 39 years. Our boats are located at a full service marina with ice, gas, snacks, drinks, beer, fishing equipment, bait and so much more. We are your one stop shop for everything you need to enjoy your time on the water. Our expert staff will guide you through the boat and give directions to local hotspots. Book with Sunset Watersports and see the difference.
5.0(3)
4 Hours
Key West
- Free cancellation
From
$475
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