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. /Historic Harbor Cruise in Key West
    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
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Historic Harbor Cruise in Key West

    Cruise Key West’s waterfront with local history narrated by a licensed captain

    5.0 stars• 74 reviews

    Duration

    3 hrs

    Ideal For

    Up to 8 people

    Includes

    Water, snacks, narration

    Highlights

    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.

    • Discover maritime history, from shipwreckers and naval history to literary legends
    • Cruise near Mallory Square, Sunset Key, harbor anchorages, and waterfront estates
    • Shape your outing around history, sightseeing, wildlife spotting, or golden-hour views
    • Relax in comfortable seating aboard a 30-foot Jeanneau yacht
    • Enjoy Perry Hotel & Marina pool and fitness center access before and after your cruise

    What's Included

    • Licensed U.S. Coast Guard captain
    • Local historical narration
    • Cooler with ice
    • Bottled water and light snacks
    • U.S. Coast Guard-certified safety equipment

    Important details

    • Arrive 15 minutes before departure
    • Primary booking party must be age 21 or older
    • Children under 18 must be accompanied by a parent or legal guardian
    • Requires boarding the vessel independently or with minimal assistance
    • Complete the required insurance waiver before arrival
    • For parties of 7–8, a designated renter age 21+ must complete a Bareboat Agreement with the captain before departure
    • Bring U.S. Coast Guard-approved life jackets for infants and toddlers
    • Fuel is not included for parties over six and costs $35 per hour
    • Captain and crew gratuity is not included; a customary minimum is 20% if satisfied
    • Do not bring open flames, and do not smoke or vape inside the cabin
    • Routes may change for weather, safety, and captain discretion
    • Excessive intoxication or unsafe behavior may result in denied boarding or an early end to the cruise without refund

    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: G9VVBR

    FAQs

    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.

    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

    Custom Charter in Key West
    Yacht Charters

    Custom Charter in Key West

    Build a private Key West day around sandbars, snorkeling, dolphins, and more

    Build a private Key West day around sandbars, snorkeling, dolphins, and more
    5.0 • 74 reviews
    $1,479& up
    Key West Wildlife Refuge Eco Charter
    Ecotours

    Key West Wildlife Refuge Eco Charter

    Explore protected Lower Keys waters with a captain-led conservation focus

    Explore protected Lower Keys waters with a captain-led conservation focus
    5.0 • 74 reviews
    $1,055
    Key West Private Sunset Cruise
    Boat Tours

    Key West Private Sunset Cruise

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

    A private evening on the water for toasts, music and horizon views
    5.0 • 74 reviews
    $1,055
    Key West 4-Hour Private Sandbar Charter
    Yacht Charters

    Key West 4-Hour Private Sandbar Charter

    Trade crowded boat routes for secluded Lower Keys sandbars

    Trade crowded boat routes for secluded Lower Keys sandbars
    5.0 • 74 reviews
    $1,267
    4-Hour Key West Reef Snorkel Charter
    Snorkeling

    4-Hour Key West Reef Snorkel Charter

    Private reef time aboard a 30-foot Jeanneau yacht

    Private reef time aboard a 30-foot Jeanneau yacht
    5.0 • 74 reviews
    $1,267
    Key West Tiki Bar Crawl Charter
    Bar and Pub Crawl

    Key West Tiki Bar Crawl Charter

    Cruise between waterfront tiki bars and restaurants with a private captain

    Cruise between waterfront tiki bars and restaurants with a private captain
    5.0 • 74 reviews
    $1,373