KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular private tours in Key West. What each trip costs, how long it runs, and who takes you out.
Private snorkel at Looe Key with a captain, all gear included, and a calm, uncrowded 3-hour outing from Big Pine Key.
Most Popular“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 beers, and hors d’oeuvres for your group.
“This was our third sunset, wine tasting, cruise with Danger in the last two years. Comfortable boat, fun and accommodating staff, good wine, tasty food, beautiful sunset.”
A private 2-hour Key West sunset cruise on a thatched tiki bar boat. BYOB, captain narration, Bluetooth music, and front-row harbor views.
“Captain Robert Bob was entertaining & educational as we cruised around the Gulf for a sunset tour!!!”
Half-day Key West private inshore fishing charter for up to 4. Live bait, tackle, and license included; target snappers, tarpon, sharks.
“Justin was an awesome guide. We caught a tarpon and nurse shark! Would 100% recommend him. Hope to be back and do it again.”
A private 2-hour sunset cruise in Key West with Stock Island Charters. See Sunset Key, Mallory Square, and quiet wildlife spots.
“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!”
Private Key West sunset sail on High Tide with refreshments and BYOB cooler. Depart from 202 William St. About 2 hours.
“It was Fantastic!!!!”
Nearly private 1.5-hour Key West JetSki tour with free pickup, sandbar swim, submarine pens, and one machine for two riders.
“Great time with Dakota on the jet ski. Two of us on one jet ski but it didn’t matter, they’re up to date models & we went plenty fast. Dakota showed us the ritzy part of town, plus a sand bar and a mangrove forest. He knew the area well and was informative without being…”
Private 4-hour backcountry fishing from Ramrod Key with shallow flats, clear-water sight fishing, and plenty of captain Q&A.
“(HUSBAND/WIFE TRIP)”
Private Key West backcountry sandbar boat trip to Snipe Keys with a friendly captain, clear water time, and calm mangrove views for up to 6.
“Destination was very easy to find to board the boat the captain was waiting for us. Don was our captain and he was very informative about the experience. There were five of us girls. we were able to bring snacks drinks snorkel gear. It was a great ride out to the sandbar where hung out…”
Private Key West sandbar and paddle from Stock Island: calm mangrove creeks, your own kayak or paddleboard time, and relaxed sandbar cruising.
“Totally worth every penny. Heather catered to us completely even down to the music we listened to. This was a laid back great day and we even brought our dog ruby and she had a blast.”
Private Key West art history walk with museum entry included, a local guide, and stops at local galleries and shops over 90 minutes.
“Seeing the art displayed at the museum of art and history, of my friends uncle, Mario Sanchez. We only wanted to go to the museum, but Lindsey and Ryan are so knowledgeable we kept on going and so glad we did. I think we could have spent the whole day with them. Highly highly highly…”
A private 3-hour snorkeling trip in Marathon, Florida with hotel pickup, live coral reefs, and flexible time for sandbar breaks.
“Hiram was a fantastic guide. He was on time, courteous and knowledgeable. We were taken out to the area called the lighthouse”
Private 3-hour Key West catamaran for up to 6: sail the coast, snorkel West Sambo reef, spot dolphins and turtles, end with sunset.
“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 them for a great time!”
Private day trip from Marathon to Key West in an air-conditioned van with live guide narration, iconic stops, and about 3 hours to roam.
“Our tour guide was very polite, accommodating, knowledgeable, and friendly. He did an exceptional job.”
Private Key West boat trip to mangrove islands and sand bars for snorkeling, paddleboarding, dolphins, and a sunset vibe, for up to six.
“Vaughn was amazing. Highly recommend for an authentic keys experience out to the sandbars. If you’re really lucky the dolphins will put on a show on your way out!”
Every way to get out on the water, and every reason to stay for the sunset.
