A private evening on the water for toasts, music and horizon views
3 hrs
Up to 8 people
Captain, fuel, safety gear
Settle into a private evening cruise designed for celebrations, proposals, and quiet time together. Bring your favorite drinks, play your music, and take in changing views from the water.
Departure – Perry Hotel & Marina Meet your captain at Dock A, Slip #32. After a brief safety overview, we cruise into calm evening waters as the golden hour begins.
Scenic Harbor & Coastal Cruise Enjoy a relaxing ride past historic waterfront homes, harbor landmarks, and open Gulf or Atlantic waters. Keep an eye out for dolphins and seabirds as the sky begins its transformation.
Prime Sunset Positioning Your captain selects the optimal viewing location based on wind and cloud patterns to ensure a spectacular sunset backdrop. Anchor or drift in a peaceful setting as the sky ignites with brilliant hues of orange, rose, and violet.
Toast the moment, take photos, enjoy music, and soak in uninterrupted panoramic views.
Twilight Return Cruise As daylight fades, cruise back under soft evening skies with the lights of Key West beginning to glow along the horizon.
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: UN24SD
Yes. For trips up to 6 passengers, each passenger must complete an insurance waiver (adults complete it for minors). For trips with a 7th and 8th passenger, the primary renter (age 21+) and the captain complete a Bareboat Agreement together at the dock before departure.
Bring any meals and beverages you want (bring your own drinks is welcome). If you have an infant or toddler, bring a U.S. Coast Guard-approved life jacket for them. Towels are not provided.
No. Captain and crew gratuity is not included; a 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.
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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