Key West · PRIVATE
39 reviewed
Out of 39 private tours on this site, these 15 are the ones to book. Prices, durations and the standout details are all here — choose in five minutes, then get back to the beach.
Private snorkel to Looe Key from Big Pine Key for up to 4 people. Gear included, 3 hours, calm-water trip led by Captain Brian.
“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 :)”
Private 2-hour Key West sunset sail on a 65-ft schooner with global wines, craft beer, and hors d’oeuvres, plus group photo time.
“Love the wine tasting, delicious appetizers and engaging crew. With the limited number of passengers, the service is first class.”
Private Key West sunset cruise on an authentic thatched tiki bar boat. BYOB drinks, captain stories, and Green Flash photos.
“Captain Morgan was great! We had a blast despite the fact it was overcast. Would definitely recommend!”
Private 4-hour Key West charter from Stock Island using live bait to target tarpon, sharks, and snappers. All tackle included.
“Trolling motor not working correctly, so lost lots of fishing time. Would not hold position, and was very noisy.wasted dayJustin was great guy.”
Private Key West sunset cruise for up to 6. Quiet viewing spots, Sunset Key and Mallory Square, bottled water, Captain Don at the helm.
“Donnie was fantastic! Very personable. He knew a lot about the area. Knew exactly where to go for a beautiful view of the sunset. I’d highly recommend this sunset cruise! The water was calm, the route was very nice. Donnie pointed out numerous landmarks. An all around great time!”
Sail on a private Key West sunset charter on the High Tide, with drinks, snacks, and a BYOB cooler for up to six.
“It was Fantastic!!!! Our crew was just excellent and we did have an enjoyable, happy and relaxing evening. Erick and Harley are the best!!”
Nearly private Key West jet ski tour with free pickup, sandbar swimming, Southernmost Point views, submarine pens, and fresh-water showers.
“Family had so much fun, everybody enjoyed sailing , kayaking, snorkeling. Boat captain Luke with his crew: Sav and Frankie made the tour fun, safe and informative. First time in a sailboat, saw a lot of species of birds and fish, able to see a sea turtle while kayaking. Enjoyed the string rays, sharks and puffer fish while kayaking. The crew was very friendly and accommodating.”
Private 4-hour fishing charter from Ramrod Key with shallow backcountry flats, clear water visuals, and Captain Jim’s hands-on coaching.
“Capt Jim was great! Very patient and most of all made sure we had a great experience. We caught a ton of fish. Would definitely do it again.”
Private Key West sandbar cruise to Snipe Keys with a small private boat, clear-water swimming time, and a local captain for up to 6.
“We had a FANTASTIC time with Captain Don! This tour is on the newer side which explains the lack of reviews, but there’s a reason why they’re all 5 stars so don’t let that deter you from booking! Captain Don has a great personality and lots of knowledge and experience on the water. The boat is gorgeous, clean, and new and the paddle board was high quality as well. The sandbar you go to is a literal shallow oasis with that tropical blue, crystal clear water you’ve been dreaming of. And we were even lucky enough to see a bunch of baby lemon sharks!! This excursion was the loveliest highlight…”
Private 3.5-hour Key West sandbar and paddle on calm mangrove waters, with a late-model pontoon, dog welcome, and bottled water.
“10/10!! Awesome time! Kids had a great time❤️. Would do it again:) We had a great time and Bethany was super helpful.”
Key West Art History private walking tour with museum admission, a one-on-one guide, and local artist stops from the Custom House to The Studios.
“Excellent tour. We visited various art related sites which were very interesting. The tour guides were extremely knowledgeable.”
Private 3-hour snorkeling in Marathon with Captain Hiram, reef time near Sombrero Lighthouse or Coffins Patch, pickup options, flexible schedule.
“Great having the whole boat to ourselves with our kids. We were picked up right at our hotel marina and went to a great snorkeling spot.”
Private 3-hour Key West catamaran for up to six: sail the coastline, snorkel West Sambo Reef, spot dolphins and turtles, watch sunset.
“Nills and Jess were friendly and attentive which made for a very relaxing day of sailing and snorkeling.”
Private Marathon-to-Key West day trip with live narration, iconic bridge views, and about 3 hours free in Key West near Duval Street.
“Our tour guide was very polite, accommodating, knowledgeable, and friendly. He did an exceptional job.”
Private Key West boat tour to mangrove islands, sandbar snorkel, dolphin spotting, and a sunset cruise for up to 6, $600.
“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. We had a dolphin and shark encounter that was very cool! Would recommend this trip to anyone!”
