Cowboy Cowgirl 36 Ft Hatteras--Since 1965 

4.5/5 (384 reviews)
 
Federally permitted
 1801 N Roosevelt Blvd, Key West, FL 33040, United States
 
Federally permitted
4.5/5 (384 reviews)
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1801 N Roosevelt Blvd
Key West, FL, United States

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 6 boats. A well-appointed 36' Hatteras sportfishing yacht, 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!

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Customer reviews

Rating summary

4.5/5
out of 5 stars from 384 reviews
Boat
4.4/5
Crew
4.7/5
Experience
4.5/5

Photos & videos by reviewers (312)

Great Service & Fish Caught!
Great Service & Fish Caught!
Great Service & Fish Caught!
+309

Angler rating

263
79
21
10
6

Anglers claimed

Good experience

87%

Appropriate for children

82%

Friendly captain

97%

Satisfied with the boat

92%

Recommend this charter

88%

Caught fish

77%

Showing 1 - 5 of 384 reviews
Showing: 5 of 384 reviews
Tim H.
Tim H.
5.0/5

Aug 7, 2025

3/4 Day Trip – Shared Charter (AM)

Captain and mate getting to know each other

VERIFIED
NEW

The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right from the start and both were vey friendly and knowledgeable. Caught some nice Mahis and Bonitas, along with few small jacks. Great time with a crew that worked hard to ensure everyone was catching fish.

The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right...  

 Tim H. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
 Tim H. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965

Roberta T.
Roberta T.
5.0/5

May 31, 2025

3/4 Day Trip – Shared Charter (AM)

Irish Cowboy 3/4 day trip

VERIFIED

Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching fish would be slim but we did catch Cero, Bonita and Mahi. Paul then took us to a spot for more action on yellow fin. We took our catch over to Mac's for them to cook, be sure to ask for Jasmine she's wonderful. Our fresh fish was so delicious. If you haven't experienced having your fish cooked for you right after your trip, you definitely need to do this!

Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching...  

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Captain replied
 Roberta T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
 Roberta T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
undefined (The Captain)
Replied on June 9, 2025
Thank you, Roberta! We’re so glad you had a wonderful day aboard the Irish Cowboy with Paul and Kris. Catching cero, bonita, and mahi sounds like a fantastic trip, and getting your fresh catch cooked up afterward is the perfect way to end the day. We’d love to have you back out with us again soon!

Dillon T.
Dillon T.
5.0/5

Jul 5, 2025

3/4 Day Trip – Shared (PM)

Great Service & Fish Caught!

VERIFIED

Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck Hand Daniel did an amazing job and definitely brought great vibes and everyone had a really fun time and captain Hans was a real joy to speak with. He had lots of experience and played some really great music I enjoyed. Just book it with these guys don’t think twice.

Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck...  

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 Dillon T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
 Dillon T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965

Robert B.
Robert B.
5.0/5

May 25, 2025

3/4 Day Trip – Shared Charter (AM)

Awesome trip for a solo angler or a couple not looking to rent the whole boat

VERIFIED

The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great choice if you were looking for something more affordable without renting the whole boat, but still with the private charter experience. The boat definitely feels like a private experience while you were on it which really benefits when fishing for anything offshore.

The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great...  

Captain replied
 Robert B. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
 Robert B. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
undefined (The Captain)
Replied on June 9, 2025
Thank you, Robert! We’re so glad you had a great experience on your shared charter. It’s wonderful to hear you enjoyed the balance of affordability and the private feel we aim to provide. We appreciate your recommendation and hope to have you back out fishing with us again soon!

Robert V.
Robert V.
5.0/5

Aug 12, 2025

3/4 Day Trip – Shared Charter (AM)

Great Day

VERIFIED
NEW

Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure everyone on board was good during the fishing expedition. Highly Recommend. A+++++++

Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure...  

Review media 0
 Robert V. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
 Robert V. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
August 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Trip – Shared Charter (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
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US $400 
Shared tour: for 2 people
Half Day Trip – Shared Charter (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
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US $400 
Shared tour: for 2 people
3/4 Day Trip – Shared Charter (AM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 8:00 AM
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US $500 
Shared tour: for 2 people
3/4 Day Trip – Shared (PM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 1:00 PM
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US $500 
Shared tour: for 2 people
Full Day Trip – Shared Charter
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
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US $600 
Shared tour: for 2 people
Inshore Shark Trip (3 hrs) (PM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 12:00 PM
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US $600 
Entire boat: up to 6 people
Inshore Shark Trip (3 hrs) (AM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 2:00 PM
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US $600 
Entire boat: up to 6 people
Inshore Shark Trip (3 hrs) (PM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 4:00 PM
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US $600 
Entire boat: up to 6 people
Reef Shark Trip (4 hrs) (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 7:00 AM
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US $800 
Entire boat: up to 6 people
Reef Shark Trip (4 hrs) (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 12:00 PM
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US $800 
Entire boat: up to 6 people
1/2 Day Trip – Private Charter (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 7:00 AM
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US $850 
Entire boat: up to 6 people
1/2 Day Trip – Private Charter (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
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US $850 
Entire boat: up to 6 people
Sunset Tuna Trip 4 hrs
FREE Cancellation 3 days notice
4 Hour Trip, starts at 2:00 PM
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US $850 
Entire boat: up to 6 people
Full Day Trip – Private Charter
FREE Cancellation 3 days notice
8 Hour Trip, starts at 7:00 AM
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US $1,350 
Entire boat: up to 6 people
10 HR Day Trip – Private Charter
FREE Cancellation 3 days notice
10 Hour Trip, starts at 7:00 AM
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US $1,550 
Entire boat: up to 6 people
12 HR Day Trip – Private Charter
FREE Cancellation 3 days notice
12 Hour Trip, starts at 7:00 AM
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US $1,750 
Entire boat: up to 6 people
12 HR Trip – Private Swordfishing
FREE Cancellation 3 days notice
12 Hour Trip, starts at 7:00 AM
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US $2,200 
Entire boat: up to 6 people
There are 23 people looking at this charter.

Customer reviews

Rating summary

4.5/5
out of 5 stars from 384 reviews
Boat
4.4/5
Crew
4.7/5
Experience
4.5/5

Photos & videos by reviewers (312)

Great Service & Fish Caught!
Great Service & Fish Caught!
Great Service & Fish Caught!
+309

Angler rating

263
79
21
10
6

Anglers claimed

Good experience

87%

Appropriate for children

82%

Friendly captain

97%

Satisfied with the boat

92%

Recommend this charter

88%

Caught fish

77%

Showing 1 - 5 of 384 reviews
Showing: 5 of 384 reviews
Tim H.
Tim H.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Captain and mate getting to know each other

VERIFIED
NEW

3/4 Day Trip – Shared Charter (AM) on August 7, 2025

The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right from the start and both were vey friendly and knowledgeable. Caught some nice Mahis and Bonitas, along with few small jacks. Great time with a crew that worked hard to ensure everyone was catching fish.

The captain was breaking in a new mate which can often be problematic, however Chris and Paul worked very well together right from the start and both were vey friendly and knowledgeable. Caught some nice Mahis and Bonitas, along with few small jacks. Great time with a crew that worked hard to ensure everyone was catching fish.  

 Tim H. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965

Roberta T.
Roberta T.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Irish Cowboy 3/4 day trip

VERIFIED

3/4 Day Trip – Shared Charter (AM) on May 31, 2025

Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching fish would be slim but we did catch Cero, Bonita and Mahi. Paul then took us to a spot for more action on yellow fin. We took our catch over to Mac's for them to cook, be sure to ask for Jasmine she's wonderful. Our fresh fish was so delicious. If you haven't experienced having your fish cooked for you right after your trip, you definitely need to do this!

Had a wonderful day with Paul and Kris! Would book this trip again. There were many other boats out there so we knew catching fish would be slim but we did catch Cero, Bonita and Mahi. Paul then took us to a spot for more action on yellow fin. We took our catch over to Mac's for them to cook, be sure to ask for Jasmine she's wonderful. Our fresh fish was so delicious. If you haven't experienced having your fish cooked for you right after your trip, you definitely need to do this!  

Review media 0
Review media 1
 Roberta T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
undefined (The Captain)
Replied on June 9, 2025
Thank you, Roberta! We’re so glad you had a wonderful day aboard the Irish Cowboy with Paul and Kris. Catching cero, bonita, and mahi sounds like a fantastic trip, and getting your fresh catch cooked up afterward is the perfect way to end the day. We’d love to have you back out with us again soon!

Dillon T.
Dillon T.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great Service & Fish Caught!

VERIFIED

3/4 Day Trip – Shared (PM) on July 5, 2025

Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck Hand Daniel did an amazing job and definitely brought great vibes and everyone had a really fun time and captain Hans was a real joy to speak with. He had lots of experience and played some really great music I enjoyed. Just book it with these guys don’t think twice.

Had a really great experience here guys. I was a single slot on the trip with another group of 🐠Fishing on the boat. The deck Hand Daniel did an amazing job and definitely brought great vibes and everyone had a really fun time and captain Hans was a real joy to speak with. He had lots of experience and played some really great music I enjoyed. Just book it with these guys don’t think twice.  

Review media 0
Review media 1
Review media 2
Review media 3
 Dillon T. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965

Robert B.
Robert B.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Awesome trip for a solo angler or a couple not looking to rent the whole boat

VERIFIED

3/4 Day Trip – Shared Charter (AM) on May 25, 2025

The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great choice if you were looking for something more affordable without renting the whole boat, but still with the private charter experience. The boat definitely feels like a private experience while you were on it which really benefits when fishing for anything offshore.

The captain and crew are awesome, the boat is clean and relatively comfortable. If you don’t mind leaning on the rail a bit. Great choice if you were looking for something more affordable without renting the whole boat, but still with the private charter experience. The boat definitely feels like a private experience while you were on it which really benefits when fishing for anything offshore.  

 Robert B. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965
undefined (The Captain)
Replied on June 9, 2025
Thank you, Robert! We’re so glad you had a great experience on your shared charter. It’s wonderful to hear you enjoyed the balance of affordability and the private feel we aim to provide. We appreciate your recommendation and hope to have you back out fishing with us again soon!

Robert V.
Robert V.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great Day

VERIFIED
NEW

3/4 Day Trip – Shared Charter (AM) on August 12, 2025

Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure everyone on board was good during the fishing expedition. Highly Recommend. A+++++++

Capt John and his First Mate Austin were great. Very friendly and Professional and knew the spots to catch. They both made sure everyone on board was good during the fishing expedition. Highly Recommend. A+++++++  

Review media 0
 Robert V. recommends Cowboy Cowgirl 36 Ft Hatteras--Since 1965

FAQs about Cowboy Cowgirl 36 Ft Hatteras--Since 1965

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
36 ft
Year built
2000
Boat manufacturer
Hatteras
Boat type
Sportfishing

Engine model
Catepillar
Powered by
2 x 700HP
Max cruising speed
18 knots
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