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“Beautiful place to snorkel and so many fish! Our captain was very knowledgeable and gave us a lot of good info, too. Highly recommend.”
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.
“My husband, 13 and 10 year old sons had a fabulous time out with Justin! They caught a huge variety of fish and came home with enough fish for dinner. They would highly recommend this charter to others!”
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.
“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…”
Private 4-hour backcountry fishing from Ramrod Key with shallow flats, clear-water sight fishing, and plenty of captain Q&A.
“Great fishing experience!! Captain Jim was very nice guide and explained everything well. My girlfriend not too experienced, also got the swing of it. A lot of activity, got 7 nice fat red snappers, also a couple of big bites that got away. Also 2 barracudas we let them out again.”
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.
“Great communication from Don as soon as we booked and a great morning on the water having to work around some weather early on. Boat is perfect for a small group and the stops he took us too were great to get a feel for the back country weaving through mangroves and stopping at 2…”
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.
“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.
“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.
“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.
“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…”
Every way to get out on the water, and every reason to stay for the sunset.
