Cruise Key West’s waterfront with local history narrated by a licensed captain
3 hrs
Up to 8 people
Water, snacks, narration
Explore Key West’s working harbor and historic waterfront from the water on a private cruise. Hear local stories while your captain shapes the route around conditions and your interests.
Cancel more than 7 calendar days before departure for a full refund. Reservations made within 7 calendar days of departure are non-refundable. Full refund if the operator cancels due to unsafe weather or other operator-initiated circumstances.
Product ID: G9VVBR
Complete the required forms before you arrive so you can depart on time. For trips up to 6 passengers, each passenger completes an insurance waiver (adults complete it for minors). For trips with a 7th and 8th passenger, the primary renter (21+) and the captain complete a Bareboat Agreement together at the dock (you may begin it before arrival).
Bring your own drinks and any additional snacks you want; meals and beverages are not included. Bring towels, and bring U.S. Coast Guard–approved infant/toddler life jackets if needed (they must be provided by the guest).
Captain and crew gratuity is not included; 20% minimum is customary if you are satisfied.
The Perry Hotel & Marina, Dock A, Slip #32, 7001 Shrimp Rd, Stock Island, FL 33040
Captains Dustin, Brian, Brian and Alexandra, Mike, Ash, Jack, Chris, and Nico collectively paint a picture of a crew that genuinely cares about showing people a good time on the water. Reviewers consistently praise how knowledgeable and personable the captains are, whether guiding guests to hidden sandbars, pointing out local history, or patiently teaching first-timers how to handle a jet ski. The boats are described as clean and well-equipped, and the team has a solid reputation for proactively working around weather to protect the experience. Beyond the boat trips, the jet ski tours get equally strong praise, with guides like Chris and Jack tailoring the pace to each group's skill level. One standout moment from a review: when weather pushed back a departure time, Chris personally called ahead to reschedule a guest's lunch reservation so nothing felt rushed. That kind of thoughtfulness comes up again and again across the reviews and seems to reflect how the whole operation runs. With a near-perfect rating across dozens of reviews, this charter is hard to argue with for anyone looking to get out on the water around Key West.
Light up the sea floor on a guided kayak paddle beneath the stars
Climb 88 steps for panoramic island views and explore the Keeper’s Quarters Museum
Cruise to a Key West sandbar for swimming, relaxing, and wildlife watching
Reef fishing for snapper and grouper, with bait and tackle included
Set your own pace at remote Key West sandbars and beaches