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. /Fishing Charters
    5. /Fish a Private Deep Sea 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
    • 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
    Gallery image
    Gallery image 2
    Gallery image 3
    Gallery image 4

    Fish a Private Deep Sea Charter in Key West

    Private 40’ sportfishing charter with air-conditioned cabin in Key West

    4.8 stars• 954 reviews
    From$1,294incl. taxes and fees

    Duration

    4-12 Hours

    Includes

    Bait, tackle, fishing license

    Highlights

    Ride offshore on the 40’ Irish Cowboy for a private Key West sportfishing trip with a professional captain and mate. Relax in the air-conditioned cabin between bites as you target species based on season and conditions.

    • Board a private 40’ sportfishing boat built for offshore conditions
    • Fish reefs, wrecks, and deep water depending on conditions
    • Target mahi, wahoo, blackfin tuna, sailfish, and marlin by season
    • Cool off in the air-conditioned cabin between bites
    • Request start times and ask about special targets like tarpon or shark

    What's Included

    • Bait
    • Tackle
    • Fishing license

    Things to know

    Fishing is weather- and conditions-dependent, and routes and target species may change. You must be able to step from dock to boat and move around a rocking deck; final participation is at the captain’s discretion.

    Cancellation Policy

    Private charters require 7 days notice. Bookings made within 24 hours of departure are non-refundable. If the operator cancels (such as adverse weather or mechanical issues), you receive a full refund. No-shows forfeit the fare.

    FAQs

    Arrive 15 minutes before your scheduled departure time. The boat departs promptly at the departure time.

    Bring a hat, sunglasses, and non-aerosol sunscreen. Bring your lunch, snacks, and drinks.

    Your charter includes bait, tackle, and a fishing license.

    Meeting details

    1801 N Roosevelt Blvd

    Experience provided by Cowboy Cowgirl Sportfishing - Knotty Cowgirl
    Experience provided by Cowboy Cowgirl Sportfishing - Knotty Cowgirl

    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

    Reference #8P54BW

    Half Day Private Charter

    $1,294.75

    4 Hours

    0

    3/4 Day Private Charter

    $1,653.40

    6 Hours

    0

    Full Day Private Charter

    $1,892.50

    8 Hours

    0

    10 Hour Private Charter

    $2,131.61

    0

    12 Hour Private Charter

    $2,370.71

    0

    Adult 4 Hr

    $159

    API

    0

    Adult 1-1

    $159

    0

    Adult 5-5

    $159

    0

    Adult 4-4

    $159

    0

    Adult 6-6

    $159

    0

    Adult 2-2

    $159

    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

    What people are saying

    Review 1 of 5
    5/5

    Had a great trip out with capt. Sam he worked hard keeping us on fish. I highly recommend them.

    Photo of Lee Brooks

    Lee Brooks

    July 9, 2026

    Review 1 of 1
    5/5

    Had a great trip out with capt. Sam he worked hard keeping us on fish. I highly recommend them.

    Photo of Lee Brooks

    Lee Brooks

    July 9, 2026

    Nearby activities

    Deep Sea Fishing Charter In Key West
    Fishing Charters

    Deep Sea Fishing Charter In Key West

    Fish offshore for mahi, tuna, sailfish, and marlin on a private charter

    Fish offshore for mahi, tuna, sailfish, and marlin on a private charter
    4.8 • 954 reviews
    $1,355& up
    Fish the Marquesas Islands on a Key West Charter
    Fishing Charters

    Fish the Marquesas Islands on a Key West Charter

    Run 20+ miles west of Key West for a full-day Marquesas fishing charter

    Run 20+ miles west of Key West for a full-day Marquesas fishing charter
    4.8 • 954 reviews
    $1,952
    Key West Deep Sea Fishing Charter
    Fishing Charters

    Key West Deep Sea Fishing Charter

    Fish Key West’s offshore waters from a stable 45-foot sportfishing boat

    Fish Key West’s offshore waters from a stable 45-foot sportfishing boat
    4.8 • 991 reviews
    $1,414& up
    Key West Light Tackle Fishing Charter
    Fishing Charters

    Key West Light Tackle Fishing Charter

    Fish reefs, shallows, and offshore edges aboard a fast 34-foot center console

    Fish reefs, shallows, and offshore edges aboard a fast 34-foot center console
    4.8 • 991 reviews
    $1,436& up
    Fish the Marquesas Islands on a Private Charter
    Private Fishing Charters

    Fish the Marquesas Islands on a Private Charter

    Run 20+ miles west of Key West to fish the remote Marquesas Keys

    Run 20+ miles west of Key West to fish the remote Marquesas Keys
    4.8 • 991 reviews
    $2,016
    Dry Tortugas Full-Day Charter
    Boat Tours

    Dry Tortugas Full-Day Charter

    Cruise to Fort Jefferson and swim in Dry Tortugas waters

    Cruise to Fort Jefferson and swim in Dry Tortugas waters
    5.0 • 375 reviews
    $2,120