Cowboy Charters - Cowboy

Captain Sean Williams of Cowboy Charters has been guiding people to fish in the Florida Keys. These waters are famous worldwide for their unusually diverse game fishery, and with two fully equipped Hatteras boats at his disposal, he has an offshore fishing trip to suit every type of angler.

Cowboy is the smaller of the company’s two boats. A well-appointed 36 ft Hatteras sportfishing yacht, this fully air-conditioned vessel makes for a comfortable ride for groups of up to six people plus the crew. The boat features a head, as well as outriggers, downriggers, and a fighting chair for a professional and comfortable fishing experience. With a large deck area, everyone will be able to get involved in the offshore action.

Captain Sean is well known for his ability to put his guests on fish, whatever their prior experience. He and his first mate will guide you across the offshore waters, providing all the know-how and equipment you need to catch species such as Mahi Mahi, Sailfish, Marlin, Wahoo, and many more. Cowboy and Cowgirl Charters’ trips usually involve a combination of trolling and bottom fishing, and you may be able to try kite fishing for Sailfish and other exciting pelagic fish when conditions allow. 

Want to make your trip extra special? Click on the charter operator’s bio below and check out Cowboy’s bigger - and even more luxurious - sister. You won’t regret it!



Select date to see available trips and rates:

  • Shared trip
    Half Day Trip – Shared Charter
    Just booked! Last booked: 9 hours ago
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    $400
    There is a $30 fuel surcharge due at the boat the morning of your trip! Trolling fairly close to shore for species such as Kingfish, Tuna, Mahi Mahi, and more. Shared charters are perfect for smaller groups who are happy to split the cost of hiring a boat with other people.
  • Shared trip
    3/4 Day Trip – Shared Charter
    In demand! Last booked: 19 hours ago
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 8:00 AM
    $500
    There is a $40 fuel surcharge due at the boat the morning of your trip! Trolling and/or bottom fishing for Tuna, Mahi Mahi, Sailfish, Snapper, and more. Shared charters are perfect for smaller groups who are happy to split the cost of hiring a boat with other people.
  • Shared trip
    Full Day Trip – Shared Charter
    In demand! Last booked: 6 days ago
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    $600
    There is a $50 fuel surcharge due at the boat the morning of your trip! Trolling and/or bottom fishing for Tuna, Mahi Mahi, Sailfish, Snapper, and more. Shared charters are perfect for smaller groups who are happy to split the cost of hiring a boat with other people.
  • Private trip
    Half Day Trip – Private Charter
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 7:00 AM
    $850
    There is a $125 fuel surcharge due at the boat the morning of your trip! This trip will usually involve trolling nearshore for species such as King Mackerel and Mahi Mahi. Special requests are welcomed, i.e. Tarpon, Shark, etc.
  • Private trip
    3/4 Day Trip – Private Charter
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 7:00 AM
    $1,150
    There is a $125 fuel surcharge due at the boat the morning of your trip! The choice is yours: troll, bottom fish, or combine the two as you fish for Mahi Mahi, Sailfish, Marlin, Tuna, Grouper, Snapper, and more.
  • Private trip
    Full Day Trip – Private Charter
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 7:00 AM
    $1,350
    There is a $125 fuel surcharge due at the boat the morning of your trip! The choice is yours: troll, bottom fish, or combine the two as you fish for Mahi Mahi, Sailfish, Marlin, Tuna, Grouper, Snapper, and more.
There are 13 people looking at this charter.

About the Charter Operator

Cowboy Cowgirl Sportfishing
Key West, Florida, United States
506 Customer Reviews
Response time 3 hours
Member since June 2014
Founded in 1965 by Hans Baumgarten, Cowboy Cowgirl Sportfishing charter is a successful family-owned and operated business. Hans' son and grandson continued the family tradition and in 1995 established the current form of the company. Cowboy Cowgirl Sportfishing boats and crew have won numerous fishing trophies in the Keys and beyond, and Captain Mark is keen on helping his guests catch prized fish.

About this listing

Targeted Species

Amberjack Amberjack
Dolphin (Mahi Mahi) Dolphin (Mahi Mahi)
Grouper (Black) Black Grouper
Grouper (Snowy) Snowy Grouper

King Mackerel (Kingfish) King Mackerel (Kingfish)
Marlin (Blue) Blue Marlin
Sailfish Sailfish
Snapper (Mutton) Mutton Snapper

Snapper (Red) Red Snapper
Tuna (Blackfin) Blackfin Tuna
Wahoo Wahoo

Boat Specs

Hatteras (Offshore sport fishing) originally built in 2000. Powered by 2 700HP Catepillar engines, with a maximum cruising speed of 18 knots.

Length
36 ft
Capacity
6 persons

Types of Fishing

Nearshore Fishing
Offshore Fishing
Reef Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Kite Fishing
Deep Sea Fishing

Amenities

Toilet
Fighting Chair
GPS
Fishfinder
Bed
Flybridge
Live Bait Well
Outriggers
Toilet
Fighting Chair
GPS
Fishfinder
Bed
Flybridge

Trip Includes

Rods, reels & tackle
Live Bait
When available!
Lures
Catch cleaning & filleting
First Mate
Fishing License

Cancellation Policy

Free cancellation up to 3 days prior to trip

Customers can cancel or modify their booking up to 3 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

Listing Policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed

Payment

Book with 10% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Visa
Mastercard
American Express
When paying the remaining balance with a credit card, an additional 3% charge will apply.

Key West Fishing Calendar

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Customer Reviews

Rating Summary
Photos & videos by reviewers (228)
Excellent
4.5 / 5
out of 5 stars from 281 reviews
Boat
Excellent
4.4 / 5
Crew
Excellent
4.7 / 5
Experience
Excellent
4.5 / 5
May fishing trip
May fishing trip
May fishing trip
+225
Angler Rating
192
60
15
8
4
Anglers Claimed
Good experience
89%
Friendly captain
98%
Recommend this charter
90%
Appropriate for children
82%
Satisfied with the boat
92%
Catch intended fish
73%
Sort By:
Featured  
Showing:
5 of 281 reviews
Kristen H.
Sugar Creek, MO
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

1/2 day with Jesse and Captain (retired) Tony!!

VERIFIED   Half Day Trip – Private Charter on January 1, 2022
These guys were so great! It was our girls first fishing trip, we booked on NYE, for New Years Day, one girl was sick, the...
Kristen H. recommends Cowboy Charters - Cowboy
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Jason J.
Howard City, MI
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Best I could imagine in 4 hours!

VERIFIED   Full Day Trip – Shared Charter on December 21, 2021
I booked a full day outing for a 4 day trip to Key West. The day I was scheduled, we got a storm, so no boats went out. I was...
Jason J. recommends Cowboy Charters - Cowboy
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1 person finds this review helpful
You and 1 other person found this review helpful
Jason J. recommends Cowboy Charters - Cowboy
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1 person finds this review helpful
You and 1 other person found this review helpful

Andrew B.
Woodfin, NC
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

A great day on the water

VERIFIED   Half Day Trip – Shared Charter on February 11, 2022
I booked a shared half day charter short notice with cowboy, just the night before we headed out. My 15-year-old son and I...
Andrew B. recommends Cowboy Charters - Cowboy
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Kristen G.
Marlboro, NJ
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip with Captain John

VERIFIED   Half Day Trip – Private Charter on October 4, 2021
We had a great time with Captain John on our half day private charter. There was an issue with Cowboy the night before we were...
Kristen G. recommends Cowboy Charters - Cowboy
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Matt A.
Greenleaf, WI
Excellent
4.3 / 5
Experience:
Very good
4.0 / 5
Boat
Excellent
5.0 / 5
Crew
Very good
4.0 / 5
Overall

3/4 shared trip

VERIFIED   3/4 Day Trip – Shared Charter on February 10, 2022
This was a shared trip so we didn’t have to pay so much. The weather was nice and sunny, but the wind was from the north,...
Matt A. recommends Cowboy Charters - Cowboy
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FAQs about Cowboy Charters - Cowboy

Cowboy Charters - Cowboy offers the following trips to customers:
  • $200 per person - Half Day Trip – Shared Charter (4 hours)
  • $250 per person - 3/4 Day Trip – Shared Charter (6 hours)
  • $300 per person - Full Day Trip – Shared Charter (8 hours)
  • $850 per group - Half Day Trip – Private Charter (4 hours)
  • $1,150 per group - 3/4 Day Trip – Private Charter (6 hours)
  • $1,350 per group - Full Day Trip – Private Charter (8 hours)

When you book a trip with Cowboy Charters - Cowboy, you can expect the following amenities onboard:
  • Toilet
  • Fighting Chair
  • GPS
  • Fishfinder
  • Bed
  • Flybridge
  • Live Bait Well
  • Outriggers

Trips booked with Cowboy Charters - Cowboy include:
  • Rods, reels & tackle
  • Live Bait (When available!)
  • Lures
  • Catch cleaning & filleting
  • First Mate
  • Fishing License

Cowboy Charters - Cowboy offers the following types of fishing:
  • Nearshore Fishing
  • Offshore Fishing
  • Reef Fishing

Cowboy Charters - Cowboy offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Kite Fishing
  • Deep Sea Fishing

Top targeted fish species with Cowboy Charters - Cowboy include:
  • Amberjack
  • Dolphin (Mahi Mahi)
  • Grouper (Black)
  • Grouper (Snowy)
  • King Mackerel (Kingfish)
  • Marlin (Blue)
  • Sailfish
  • Snapper (Mutton)
  • Snapper (Red)
  • Tuna (Blackfin)
  • Wahoo