Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Stock Island…
    3. /Water Activities
    4. /Boat Tours
    5. /Key West Private Sunset Cruise
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Product image 8
    Product image 9
    Product image 10
    Product image 11
    Product image 12
    Product image 13
    Product image 14
    Product image 15
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Key West Private Sunset Cruise

    A private evening on the water for toasts, music and horizon views

    5.0 stars• 74 reviews

    Duration

    3 hrs

    Ideal For

    Up to 8 people

    Includes

    Captain, fuel, safety gear

    Highlights

    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.

    • Celebrate an engagement, anniversary, honeymoon, or special night together
    • Bring your own champagne and other drinks
    • Play your favorite music aboard
    • Plan a proposal in advance for discreet captain assistance
    • Enjoy complimentary pool and fitness center access before and after your cruise

    Itinerary

    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.

    What's Included

    • Cooler with ice
    • Bottled water
    • Light snacks
    • Comfortable seating
    • U.S. Coast Guard-certified safety equipment

    Important details

    • Arrive 15 minutes before departure
    • Complete an insurance waiver for every passenger before arrival
    • A parent or legal guardian must accompany anyone under 18
    • The primary booking party must be age 21 or older
    • Groups of 7–8 require a designated renter age 21+ to complete a Bareboat Agreement with the captain before departure
    • Requires boarding independently or with minimal assistance
    • Bring a U.S. Coast Guard-approved life jacket for infants and toddlers
    • Fuel for groups over 6 is not included in the listed price and costs $35 per hour
    • Captain and crew gratuity is not included in the listed price; the customary minimum is 20% if satisfied
    • Smoking or vaping is not permitted inside the cabin, and open flames are not permitted onboard
    • Avoid excessive intoxication or unsafe behavior, which may result in denied boarding or early termination

    Cancellation Policy

    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

    FAQs

    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.

    Meeting details

    The Perry Hotel & Marina, Dock A, Slip #32, 7001 Shrimp Rd, Stock Island, FL 33040

    Experience provided by Six Fins Boat Charter - Perry Marina

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Private Charter

    $1,054.70

    Up to 8 People.

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    74 reviews•Google Maps
    67
    0
    0
    0
    0

    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.

    What people are saying

    Review 1 of 3
    5/5

    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.

    Photo of Tawny Greenbaum

    Tawny Greenbaum

    July 20, 2026

    Review 1 of 1
    5/5

    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.

    Photo of Tawny Greenbaum

    Tawny Greenbaum

    July 20, 2026

    Nearby activities

    Key West Guided Night Kayak Tour
    Kayaking Tours

    Key West Guided Night Kayak Tour

    Light up the sea floor on a guided kayak paddle beneath the stars

    4.8 • 996 reviews
    $93/ kayak
    Climb Key West Lighthouse & Visit Keeper's Quarters
    Historical Sites and Monuments

    Climb Key West Lighthouse & Visit Keeper's Quarters

    Climb 88 steps for panoramic island views and explore the Keeper’s Quarters Museum

    4.6 • 508 reviews
    $17/ person
    4-Hour Sandbar Cruise in Key West
    Boat Tours

    4-Hour Sandbar Cruise in Key West

    Cruise to a Key West sandbar for swimming, relaxing, and wildlife watching

    $596
    5-Hour Reef Fishing Trip in Key West
    Fishing Charters

    5-Hour Reef Fishing Trip in Key West

    Reef fishing for snapper and grouper, with bait and tackle included

    5.0 • 841 reviews
    $89/ person
    Key West Parasailing with Dry Take-Offs & Landings
    Parasailing

    Key West Parasailing with Dry Take-Offs & Landings

    Parasail above Key West on a 12-passenger boat with tandem flight options

    4.9 • 12.7K reviews
    $74/ person
    Dive 2-Tank Private Charter in Key West
    Scuba Diving

    Dive 2-Tank Private Charter in Key West

    Charter a private 2-tank dive with an in-water dive master

    4.9 • 330 reviews
    $1,192& up