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
Check Availability →Read my full review →
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
Check Availability →Read my full review →
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“Great tour and history of Key West. AJ is delightful & accommodating & well-known. Enjoyable way to see all of Key West.”
★★★★★★★★★★
68 reviews2 hours 30 minutes (approx.)From $180.00by Florida Keys Ventures
Check Availability →Read my full review →
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“Trisha was funny and knowledgeable. We had nice tour of the area before settling in for our sunset. Well worth the money to have this cute little tiki boat all to yourselves.”
★★★★★★★★★★
67 reviews2 hours (approx.)From $456.88by Tiki Boat Adventures
Check Availability →Read my full review →
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
Check Availability →Read my full review →
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
Check Availability →Read my full review →
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
Check Availability →Read my full review →
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“We can’t say enough about Captain Jim. He is a great guide and went far beyond making our first saltwater fishing experience the best ever!! He definitely knows his fish and will put you exactly in a position to catch every time you cast. He…”
★★★★★★★★★★
45 reviews4 hours (approx.)From $500.00by Mile Marker 27 Fishing Charters
Check Availability →Read my full review →
Yearning for a secluded escape?
★ 5.0“Our trip was absolutely phenomenal! Don took us to some incredible spots, and my husband and I truly enjoyed the engaging conversation along the way. He was wonderfully attentive to our children, which we greatly appreciated. The weather was a mix of clouds, sunshine, and…”
★★★★★★★★★★
39 reviews3 hours (approx.)From $550.00by Stock Island Charters
Check Availability →Read my full review →
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!
“Our captain took us to a great spot we swam, paddle board and we’re able to spot some stingrays and sharks. It was awesome we had so much fun!”
★★★★★★★★★★
36 reviews3 hours 30 minutes (approx.)From $600.00by Lazy Dog Adventures
Check Availability →Read my full review →
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“Excellent tour. We visited various art related sites which were very interesting. The tour guides were extremely knowledgeable.”
★★★★★★★★★★
35 reviewsFrom $59.99by Key West Art History Tour
Check Availability →Read my full review →
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
Check Availability →Read my full review →
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“Sitting in the netting of the catamaran and watching the water go bye The snorkeling was awesome. We went out to the reefs. He was able to post up while we snorkels.”
★★★★★★★★★★
26 reviewsFrom $0.00by Bimini Charters
Check Availability →Read my full review →
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!
“Troy was our driver and was the best! He made sure that he gave us information so that we could make choices about where to go and what to see. His knowledge of the Keys and Key West was so entertaining and helpful. Hands down,…”
★★★★★★★★★★
26 reviews8 hours (approx.)From $137.00by Up The Keys Tours
Check Availability →Read my full review →
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
Check Availability →Read my full review →