Cruise between waterfront tiki bars and restaurants with a private captain
4 Hours
Up to 8 people
Private captain, ice & water
Cruise Key West’s harbor between waterfront tiki bars and dockside restaurants on a private charter. Food and beverages are purchased separately at each venue, while your captain handles cruising and docking.
Cancellations made more than 7 calendar days before departure receive 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: RSKWYD
Complete the required waiver in advance so you can depart on time. If you bring a 7th or 8th passenger, the primary renter (21+ years old) and the captain must complete a bareboat agreement together at the dock before departure. Bring a government-issued photo ID for check-in.
Buy food and beverages directly at each venue. Captain gratuity is not included (customary 20% minimum if satisfied). Towels and infant/toddler life jackets are not included; bring your own life jackets for infants/toddlers.
Bring towels if you want them, and bring infant/toddler life jackets if needed. Do not bring illegal drugs or open flames. Do not use glass containers while the boat is underway.
The Perry Hotel & Marina, Dock A, Slip #32, 7001 Shrimp Rd, Stock Island, FL 33040
Perched along the working waterfront of Key West, The Perry Hotel & Marina Key West puts you steps from the salt air and bobbing masts of a genuine working marina. The open-air spaces, sun-bleached wood, and breezy common areas capture the easy rhythm of island life. At The Perry Hotel & Marina Key West, the Gulf light shifts from gold to rose at dusk, and the sound of water lapping against hulls sets the tone for every evening. It is a place where the boundary between land and sea feels pleasantly thin.
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.
We went out with captain Patrick and had the best time! He knew exactly where to take us and was so accommodating. He even helped us catch bait fish with a net when we realized we forgot bait! He taught my family how to do it too! Core memories were made on this boat trip. Best part of our Key West stay.
Tawny Greenbaum
July 20, 2026
We went out with captain Patrick and had the best time! He knew exactly where to take us and was so accommodating. He even helped us catch bait fish with a net when we realized we forgot bait! He taught my family how to do it too! Core memories were made on this boat trip. Best part of our Key West stay.
Tawny Greenbaum
July 20, 2026
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