Key West
The private bookings: charters, snorkel runs and island days with the boat to yourselves. On a four-mile island, the water is where private pays off.
Discover the Florida Keys' vibrant coral reefs on a private snorkel trip from Big Pine Key, led by knowledgeable guides in calm, pristine waters.
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 :)”
Experience a private Key West sunset aboard a charming tiki bar boat, enjoying stunning views, personalized service, and BYOB in a relaxed setting.
“What an amazing experience. Stunning sunset, dolphins swam with us, Robbert had alot of knowledge about the islands & was very fun to be around. Great family time. Highly recommend it. Many thanks kate”
Experience Key West's vibrant waters on a private half-day inshore fishing charter. Perfect for all skill levels, with expert guides and plentiful marine life.
“We had such an amazing time. Captain Jagger was awesome! Went to a few spots and caught a number of fish and two sharks (released). The kids had an awesome time and reeled in a few!”
Experience a private sunset cruise around Key West with expert guides, stunning views, and marine wildlife, perfect for romantic or relaxed evenings.
“Don was amazing and so accommodating given the weather that we had. He shared his experiences and knowledge while taking us all around the island then stopping for a beautiful sunset.”
Experience nearly private, guided jet ski tours around Key West’s iconic sights, with stops at sandbars and expert guides ensuring fun and safety.
“Dakota did a great job taking us on our jet ski tour. We started a little late due to getting fueled up but this is the best way to see key west! We had so much fun!”
Experience a private sunset sail off Key West, enjoy stunning views, soft drinks, and the peaceful ocean breeze—all for a great value at $695 per group.
“It was Fantastic!!!! Our crew was just excellent and we did have an enjoyable, happy and relaxing evening. Erick and Harley are the best!!”
Discover the backcountry of the Florida Keys on a private fishing trip from Ramrod Key. Enjoy expert guides, abundant fish, and personalized service.
“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.”
Discover the beauty of the Florida Keys with a private sandbar adventure, paddleboarding, snorkeling, and wildlife spotting in tranquil backcountry.
“Donnie, thank you for the great time that you helped make happen with my family and I. I would recommend anyone looking to have a great time on the water to contact Stock Island Charters, you will definitely not be disappointed!”
Discover the serene beauty of Key West with a private boat tour exploring mangroves, paddling, and relaxing on sandbars—perfect for eco-adventurers.
“10/10!! Awesome time! Kids had a great time❤️. Would do it again:) We had a great time and Bethany was super helpful.”
Discover Key West's vibrant art scene with this private, 1.5-hour tour exploring museums, galleries, and local artists—perfect for culture lovers.
“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…”
Discover a private 3-hour snorkeling adventure in Marathon, Florida, with flexible activities, expert guides, and stunning marine wildlife.
“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.”
Enjoy a personalized 3-hour private catamaran sail along Key West's coast, snorkeling at prime reefs, and relaxing with your own food and drinks.
“What an outstanding experience…from reservations through the day out with Nils and Patrick! Our family had a great time!!!”
Discover the best of Key West on a private day trip from Marathon, with sightseeing, free time, and optional add-ons like sunset sails—perfect for a quick getaway.
“Scott did a wonderful job keeping us entertained and educated during the entire trip. He was always available at a moments notice to take us to the next location. I would highly recommend and will use them again if we get the chance!”
Experience stunning sunset views, dolphin sightings, and vibrant snorkel adventures on a private boat tour through Key West’s beautiful waters for up to 6 guests.
“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.…”
Experience a private 4-hour sandbar cruise in Key West on a tiki bar boat. Enjoy sunshine, water activities, and stunning views with friends or family.
“we had six ladies on a Saturday afternoon tiki cruise with Captain Madison. Madison was amazing! she took us to a beautiful spot and we enjoyed our day so much. Everyone in the group talked about it the whole weekend. it was everyone's favorite thing…”
Schooners at sunset, reef by morning and Duval Street in between.