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.
“Love the wine tasting, delicious appetizers and engaging crew. With the limited number of passengers, the service is first class.”
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.
“If you are looking for an outstanding private fishing tour, pick this one. Our guide Justin was great. We caught some great fish and even a couple sharks.”
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.
“Do not hesitate to book with Capt. Jim. He is very professional, incredibly knowledgeable, and patient.”
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.
“Amazing private boat tour through mud flats. Found several hidden beaches. Our guide was fun and knowledgeable.”
Private Key West art history walk with museum entry included, a local guide, and stops at local galleries and shops over 90 minutes.
“Excellent tour. We visited various art related sites which were very interesting. The tour guides were extremely knowledgeable.”
A private 3-hour snorkeling trip in Marathon, Florida with hotel pickup, live coral reefs, and flexible time for sandbar breaks.
“We had rougher seas than anticipated, but our captain made sure he found us calm waters in which my family good relax and enjoy both snorkeling and beach combing for shells. Top notch equipment super personable captain and plenty of refreshments.”
Private 3-hour Key West catamaran for up to 6: sail the coast, snorkel West Sambo reef, spot dolphins and turtles, end with sunset.
“The captain and the first mate were amazing and helpful. Knowledgeable and kind. The boat was beautiful and well equipped and maintained. They helped with getting in the water and refreshments. The water was incredible, they pointeRead more”
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.
“We had an incredible private tour from Marathon to Key West, and it was truly one of the highlights of our time in the Keys. Troy is incredibly knowledgeable and brought the history of the islands to life with fascinating stories, fun facts, and great local insight.”
Private Key West boat trip to mangrove islands and sand bars for snorkeling, paddleboarding, dolphins, and a sunset vibe, for up to six.
“Amazing Tour with Captain Vaughn.”
Every way to get out on the water, and every reason to stay for the sunset.
