Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Key West…
    3. /Water Activities
    4. /Yacht Charters
    5. /4-Hour Private Cruise Charter 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
    Gallery image

    4-Hour Private Cruise Charter in Key West

    Charter Cowfish for a 4-hour private cruise with any two water activities

    4.9 stars• 414 reviews

    Duration

    4 hours

    Ideal For

    Up to 6 people

    Includes

    Snorkel gear, snacks, water

    Highlights

    Set out on a 4-hour private charter aboard Cowfish, a Glacier Bay power catamaran for up to 6 passengers. Choose any two activities—snorkeling, visiting a sandbar, or searching for dolphins—with an experienced captain.

    • Choose two activities for your 4-hour private trip
    • Snorkel at a chosen spot with provided instruction and gear
    • Cruise with only your group and an experienced captain
    • Bring your own drinks and extra snacks if you’d like
    • Meet directly at the boat for check-in with your captain

    What's Included

    • Snorkeling equipment
    • Flotation gear
    • Snorkeling instruction
    • Fuel
    • Fresh organic snacks
    • Bottled water
    • Wet suits during the winter months

    Things to know

    Customary gratuity is 10–20% and is not required. Groups of 6 or more have an automatic 20% gratuity added after the reservation is made.

    Split the cost with your group

    This booking is for the whole experience, which fits up to 6 guests.

    From$141per person
    Split with

    Cancellation Policy

    For private charters, you can get a refund until 30 days before scheduled boarding time. Within 30 days, no refunds or rescheduling. Runs in light rain and moderate conditions; the seller may cancel for severe or unsafe weather. If the seller cancels, reschedule (subject to availability) or get a full refund.

    Product ID: 47WDTT

    FAQs

    Bring reef-safe sunscreen, a swimsuit, a towel, and layered clothes from November–March. You may bring additional snacks and drinks, but do not bring spray sunscreen.

    Filtered water is provided. You can bring your own drinks and any extra snacks you’d like.

    Yes. Snorkeling instruction is included along with snorkeling equipment and flotation gear.

    Experience provided by Blu Q Catamaran

    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

    $846.94

    Fits up to 6 guests · 4 hours

    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

    4.9
    Excellent
    414 reviews•Google Maps
    370
    3
    6
    2
    6

    Smalls, Hadden, and the rest of the crew have built a serious reputation for making people feel welcome on the water. The vibe is relaxed and judgment-free, with most trips centered around snorkeling at the coral reef, walking a sandbar ten miles offshore, or simply soaking up the sun on the catamaran. Wildlife sightings, including sharks, dolphins, and turtles, come up often enough to feel like a genuine bonus rather than a lucky fluke. The all-male day sail draws a loyal crowd, with plenty of repeat visitors and couples celebrating special trips. Guests consistently praise the crew's energy and attentiveness, and the food and drink offerings get strong marks too. If you're on the fence, the reviews here make a pretty clear case to just go ahead and book it.

    What people are saying

    Review 1 of 5
    5/5

    First time sailing with Captain Smalls and First mate Haddon Labor day weekend. They work well as a team and enhance the experience! All around wonderful time from beginning to end. Fun on the water with nice group of men and shedding the clothes is icing on the cake!. Thanks guys!

    Photo of Michael Spatz

    Michael Spatz

    September 9, 2026

    Review 1 of 1
    5/5

    First time sailing with Captain Smalls and First mate Haddon Labor day weekend. They work well as a team and enhance the experience! All around wonderful time from beginning to end. Fun on the water with nice group of men and shedding the clothes is icing on the cake!. Thanks guys!

    Photo of Michael Spatz

    Michael Spatz

    September 9, 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