Captain 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’ 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.

The captain 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
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    US $400
    There is a $30 per person 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
    Half Day Trip – Shared Charter
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    US $400
    There is a $30 per person 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
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 8:00 AM
    US $500
    There is a $40 per person 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
    Just booked! Last booked: 8 hours ago
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    US $600
    There is a $50 per person 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
    Sunset Tuna Trip 4 hrs
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 2:00 PM
    US $850
    There is a $150 fuel surcharge due on the morning of your trip! The trip will usually involve trolling nearshore for species such as King Mackerel and Mahi Mahi, but you can also get in touch with your captain if there's a specific species you'd like to go after. The inshore waters can come alive with Tarpon and Shark, so make the most of whatever's biting during the season.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
  • Private trip
    3/4 Day Trip – Private Charter
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 7:00 AM
    US $1,150
    There is a $150 fuel surcharge due on the morning of your trip! The trip will usually involve trolling nearshore for species such as King Mackerel and Mahi Mahi, but you can also get in touch with your captain if there's a specific species you'd like to go after. The inshore waters can come alive with Tarpon and Shark, so make the most of whatever's biting during the season.
  • Private trip
    Full Day Trip – Private Charter
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 7:00 AM
    US $1,350
    There is a $150 fuel surcharge due on the morning of your trip! The trip will usually involve trolling nearshore for species such as King Mackerel and Mahi Mahi, but you can also get in touch with your captain if there's a specific species you'd like to go after. The inshore waters can come alive with Tarpon and Shark, so make the most of whatever's biting during the season.
  • Private trip
    10 HR Day Trip – Private Charter
    FREE Cancellation 3 days notice
    10 Hour Trip, starts at 7:00 AM
    US $1,550
    There is a $150 fuel surcharge due on the morning of your trip! The trip will usually involve trolling nearshore for species such as King Mackerel and Mahi Mahi, but you can also get in touch with your captain if there's a specific species you'd like to go after. The inshore waters can come alive with Tarpon and Shark, so make the most of whatever's biting during the season.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Amberjack
    Amberjack
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Marlin (Blue)
    Blue Marlin
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Shark (Hammerhead)
    Hammerhead Shark
    Snapper (Mutton)
    Mutton Snapper
    Tuna (Blackfin)
    Blackfin Tuna
    Shark (Bull)
    Bull Shark
    Grouper (Snowy)
    Snowy Grouper
  • Private trip
    12 HR Day Trip – Private Charter
    FREE Cancellation 3 days notice
    12 Hour Trip, starts at 7:00 AM
    US $1,750
    There is a $150 fuel surcharge due on the morning of your trip! The trip will usually involve trolling nearshore for species such as King Mackerel and Mahi Mahi, but you can also get in touch with your captain if there's a specific species you'd like to go after. The inshore waters can come alive with Tarpon and Shark, so make the most of whatever's biting during the season.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Amberjack
    Amberjack
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Marlin (Blue)
    Blue Marlin
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Shark (Hammerhead)
    Hammerhead Shark
    Snapper (Mutton)
    Mutton Snapper
    Tuna (Blackfin)
    Blackfin Tuna
    Shark (Bull)
    Bull Shark
    Grouper (Snowy)
    Snowy Grouper
There are 12 people looking at this charter.

Customer reviews

Rating summary
Excellent
4.5 / 5
out of 5 stars from 342 reviews
Boat
Excellent
4.4 / 5
Crew
Excellent
4.7 / 5
Experience
Excellent
4.4 / 5
Photos & videos by reviewers (281)
A crew that knows everything about fishing in the Keys!
Great Day Mahi
Great Day Mahi
+278
Angler rating
233
74
20
8
5
Anglers claimed
Good experience
87%
Friendly captain
97%
Recommend this charter
89%
Appropriate for children
81%
Satisfied with the boat
92%
Caught fish
75%
Sort by:
Featured  
Showing:
5 of 342 reviews
Nicholas P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

A crew that knows everything about fishing in the Keys!

VERIFIED   NEW  3/4 Day Trip – Shared Charter on July 4, 2024
I had a fantastic time on the group trip(6 hours) left with enough Mahi to feed 10. Fantastic people that are very helpful...
Nicholas P. recommends Cowboy Charters – Cowboy Since 1965
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Nicholas P. recommends Cowboy Charters – Cowboy Since 1965
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Michael S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Key West fishing trip

VERIFIED   Sunset Tuna Trip 4 hrs on May 31, 2024
The crew of Cole and Steve were EXCEPTIONAL!!  It was quite windy and one of our guests could not handle the rough seas. ...
Michael S. recommends Cowboy Charters – Cowboy Since 1965
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  Cowboy Cowgirl Sportfishing Charters Charter Operator replied

Lisa C.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Never Give Up!

VERIFIED   Full Day Trip – Shared Charter on April 14, 2024
After several hours of deep trolling with no bites and uncooperative seas, Cap’n Cole changed to shallower trolling for mutton...
Lisa C. recommends Cowboy Charters – Cowboy Since 1965
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Lisa C. recommends Cowboy Charters – Cowboy Since 1965
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Robert W.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Irish Cowboy was Excellent

VERIFIED   3/4 Day Trip – Shared Charter on March 12, 2024
The captain put us on fish and the first mate was very helpful, both were courteous and professional.  We had 2 sailfish on...
Robert W. recommends Cowboy Charters – Cowboy Since 1965
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  Cowboy Cowgirl Sportfishing Charters Charter Operator replied

Jeremy G.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Day Mahi

VERIFIED   NEW  3/4 Day Trip – Shared Charter on July 2, 2024
Mahi were caught this day!!! Great Captain and Crew… many boats came back empty handed the is day we rolled in heavy!!!
Jeremy G. recommends Cowboy Charters – Cowboy Since 1965
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Jeremy G. recommends Cowboy Charters – Cowboy Since 1965
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FAQs about Cowboy Charters – Cowboy Since 1965

Cowboy Charters – Cowboy Since 1965 offers the following trips to customers:
  • US $200 per person - Half Day Trip – Shared Charter (4 hours)
  • US $200 per person - Half Day Trip – Shared Charter (4 hours)
  • US $250 per person - 3/4 Day Trip – Shared Charter (6 hours)
  • US $300 per person - Full Day Trip – Shared Charter (8 hours)
  • US $850 per group - Sunset Tuna Trip 4 hrs (4 hours)
  • US $1,150 per group - 3/4 Day Trip – Private Charter (6 hours)
  • US $1,350 per group - Full Day Trip – Private Charter (8 hours)
  • US $1,550 per group - 10 HR Day Trip – Private Charter (10 hours)
  • US $1,750 per group - 12 HR Day Trip – Private Charter (12 hours)

When you book a trip with Cowboy Charters – Cowboy Since 1965, you can expect the following amenities onboard:
  • Toilet
  • Fighting Chair
  • GPS
  • Fishfinder
  • Bed
  • Flybridge
  • Live Bait Well
  • Outriggers
  • Spearfishing Equipment
  • Ice Box coolers with ice

Trips booked with Cowboy Charters – Cowboy Since 1965 include:
  • Rods, reels & tackle
  • Live Bait (When available!)
  • Lures
  • Catch cleaning & filleting
  • First Mate
  • Fishing License

Cowboy Charters – Cowboy Since 1965 offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Offshore Fishing
  • Reef Fishing
  • Wreck Fishing

Cowboy Charters – Cowboy Since 1965 offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Spinning
  • Jigging
  • Kite Fishing
  • Deep Sea Fishing

Top targeted fish species with Cowboy Charters – Cowboy Since 1965 include:
  • Amberjack
  • Barracuda (Great)
  • Grouper (Black)
  • Grouper (Snowy)
  • Marlin (Blue)
  • Shark (Blacktip)
  • Shark (Bull)
  • Shark (Hammerhead)
  • Snapper (Mutton)

Meet the Charter Operator

Cowboy Cowgirl Sportfishing Charters
Key West, Florida, United States
ID & license verified
614 Customer reviews
Response time within an hour
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
Barracuda (Great) Great Barracuda
Grouper (Black) Black Grouper
Grouper (Snowy) Snowy Grouper

Boat specs

Hatteras (Sportfishing) 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

Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing

Fishing techniques

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

Amenities

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

You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

Listing policies

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

Payment

Pay online in full

Pay online in full through FishingBooker and save on credit card fees at the dock.

No additional fees.
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
PayPal
When paying the remaining balance with a credit card, an additional 3.5% charge will apply.

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