A private charter in Key West means your own boat, your own guide, and nobody else’s schedule; these are the ones I’d book. Crews will bend the route toward sandbars, snorkel spots, or a sunset anchorage. Small groups get the most out of the island this way.
Discover the hidden underwater paradise with a private snorkeling adventure in Looe Key from Big Pine Key. Dive into crystal-clear waters and explore vibrant coral reefs today!
Most Popular★ 5.0“Loved spending time with Captain Brian and learning so much from him! He was patient with our girls wanting to dive out of the boat! Thank you :)”
★★★★★★★★★★
431 reviews3 hours (approx.)From $575.00by Keys Boat Tours
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Experience the magic of Key West with our private 2-hour Wind and Wine Sunset Sail. Sip fine wines while sailing into the breathtaking sunset. Book now!
★ 5.0“Love the wine tasting, delicious appetizers and engaging crew. With the limited number of passengers, the service is first class.”
★★★★★★★★★★
87 reviewsFrom $4,000.00by Danger Charters
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Experience the ultimate Conch Republic adventure on the Private Key West Tiki Bike! Discover Key West's hidden gems while cruising in style with Kokomo Cabs.
★ 5.0“Was a great intro to the history and some of the quirky facts about Key West. AJ was simply the best. He knew tons of facts about Key West and made the entire trip fun. Would not hesitate to recommend him.”
★★★★★★★★★★
68 reviews2 hours 30 minutes (approx.)From $180.00by Florida Keys Ventures
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Experience the ultimate Key West sunset on a private Tiki Bar boat. Sip tropical drinks, enjoy breathtaking views, and create unforgettable memories. Book your 2-hour cruise now!
★ 4.5“Great way to see Key West and gorgeous sunset. Trisia our captain was super nice and great for a relaxing cruise!”
★★★★★★★★★★
67 reviews2 hours (approx.)From $456.88by Tiki Boat Adventures
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Experience the thrill of inshore fishing in Key West with our private charter. Catch trophy fish and create memories that will last a lifetime. Book your adventure now!
★ 5.0“Jaager was a great guide. Knowledgeable, resourceful and making a wonderful memory for our family. Jaager cleaned the fish and made arrangements to have it for lunch near the dock. So fresh, delicious- great day!”
★★★★★★★★★★
64 reviews4 hours (approx.)From $750.00by Live Action Sportfishing 2
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Fulfill your dreams of a luxurious sunset cruise around Key West, where exclusivity meets breathtaking views - find out what makes this experience unforgettable.
★ 5.0“Highly recommend! The whole experience was super smooth and tailored to what we were hoping for. We went all over, explored a variety of sights, walked across a sandbar, cruised thru the mangroves, saw some of Key West’s nicest houses, and learned a ton. Captain…”
★★★★★★★★★★
59 reviews2 hours (approx.)From $400.00by Stock Island Charters
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Experience the breathtaking beauty of a Private Key West Sunset Sail. Set sail on a romantic adventure and create unforgettable memories. Book your exclusive voyage now!
★ 4.5“It was Fantastic!!!! Our crew was just excellent and we did have an enjoyable, happy and relaxing evening. Erick and Harley are the best!!”
★★★★★★★★★★
49 reviews2 hours (approx.)From $695.00by Sunset Sail Key West
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Experience the ultimate fishing adventure with our private fishing charter from Ramrod Key. Catch trophy fish and make memories that will last a lifetime. Book your trip now!
★ 5.0“Captain Jim was very personable and knowledgeable. The equipment was great, boat was clean. He worked very hard to make sure we caught fish! Thank you Captain Jim for a great time. We took the fish to Dante’s in Key West. Best fish dinner ever!”
★★★★★★★★★★
45 reviews4 hours (approx.)From $500.00by Mile Marker 27 Fishing Charters
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Yearning for a secluded escape?
★ 5.0“Captain Don was outstanding. He was extremely knowledgeable of the area and was willing to answer any question. I would recommend him as your guide. We look forward to utilizing his services again”
★★★★★★★★★★
39 reviews3 hours (approx.)From $550.00by Stock Island Charters
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Experience the ultimate adventure in Key West! Explore hidden sandbars, snorkel vibrant coral reefs, and relax on a private boat. Book your unforgettable getaway now!
“Nicole was excellent. Very informative and new all the cool spots. Parking was easy and the boat was right there. She took us around the mangroves and gave us a nice cayak to explore on our own. Very nice pontoon boat with a leisurely drive…”
★★★★★★★★★★
36 reviews3 hours 30 minutes (approx.)From $600.00by Lazy Dog Adventures
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Discover the vibrant art scene of Key West on a private tour. Uncover the hidden stories behind iconic artworks and immerse yourself in the rich art history of this captivating destination.
★ 5.0“Our Key West Art tour with Lindsey was everything we hoped for - and more. Lindsey was energetic, a great listener, and very knowledgeable. The tour was impressive and we would definitely recommend! We felt like "insiders!"”
★★★★★★★★★★
35 reviewsFrom $59.99by Key West Art History Tour
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Wonders await as you embark on a private snorkeling tour in Marathon, Florida, but there's a hidden surprise that will leave you wanting more.
★ 5.0“Highly recommend Captain Hiram for a private trip. Professional, courteous and knowledgeable. We will book with him next time we are in the area!”
★★★★★★★★★★
31 reviewsFrom $720.00by Hiram Machado
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Experience the ultimate luxury sailing adventure on our owner-operated catamaran. Enjoy private charters with unparalleled service and breathtaking views. Book your dream getaway today!
★ 5.0“What a great day on the water! The captain, Nils, was super nice and took us where ever we wanted to go! The first mate, Simon…aka Chester, was a good sport, friendly, and super helpful! Ashley was very responsive to our questions! I HIGHLY recommend…”
★★★★★★★★★★
26 reviewsFrom $0.00by Bimini Charters
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Explore the stunning Florida Keys with our exclusive private tour. From Marathon to Key West, uncover hidden gems and create unforgettable memories. Don't miss out!
“Scott was very knowledgeable about the area. He was very personable and made the trip enjoyable. Would highly recommend.”
★★★★★★★★★★
26 reviews8 hours (approx.)From $137.00by Up The Keys Tours
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Uncover the magic of a Private Boat Tour to Sand Bar Snorkel Dolphins and Sunset, where unforgettable surprises await at every turn.
★ 5.0“Great experience! There was a mistake from the booking site on the time of our tour. Vaughn handled it very well, but I would suggest verifying your time the night before. Vaughn took us to several islands to enjoy snorkeling, paddle boarding, site seeing, etc.…”
★★★★★★★★★★
25 reviews3 hours 30 minutes (approx.)From $600.00by Vaughn Willis
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