Cowboy Cowgirl 36 Ft Hatteras--Since 1965 

4.5/5 (405 reviews)
 
Federally permitted
 1801 N Roosevelt Blvd, Key West, FL 33040, United States

Cowboy Cowgirl 36 Ft Hatteras--Since 1965 

 
Federally permitted
4.5/5 (405 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 405 reviews
Boat
4.4/5
Crew
4.7/5
Experience
4.5/5

Photos & videos by reviewers (367)

amazing time, so much fish!
amazing time, so much fish!
amazing time, so much fish!
+364

Angler rating

279
80
23
11
6

Anglers claimed

Good experience

87%

Appropriate for children

82%

Friendly captain

97%

Satisfied with the boat

91%

Recommend this charter

88%

Caught fish

77%

Showing 1 - 5 of 405 reviews
Showing: 5 of 405 reviews
LORETTA Daniel
LORETTA Daniel
5.0
Verified
New
Difficult week but Cowboy Cowgirl came through
Full Day Trip – Shared Charter on December 15, 20252 adults
We went to Key West just for the fishing trip then wind came up and nothing could go out. They worked with us and took us out our last day. We had hoped for some big boys, sailfish, etc but at this point we just wanted to have fun. The captain Hans managed some rough water and our first mate worked hard to help us all catch fish and that we did. Lots of maceral, snapper and yellow tail and even the odd mutton and blue wrasse. When we got back they were waiting to drive us to the airport to catch our flight. I can't recommend enough how hard they worked to make our trip good and get fish.
0
Alex Moorhead
Alex Moorhead
5.0
Verified
True Key West experience
3/4 Day Trip – Shared Charter (AM) on August 23, 20252 adults
My wife and I went out on Cowboy Cowgirl with Tom and Will and it was a blast. We did the 3/4 day and it was a good amount of fishing time. The ride out to there took about an hour out and back so that’s already leaving you with only 4 hours of fishing time for us and 4 other people. Tom and Will knew a lot about the area and the fish we were looking for. Will guided everyone on what to do and let us learn and experience it ourselves too. We caught a huge haul and Will filleted it and gave us each some to take home. Definitely would recommend! I already plan to come back.
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Reported catch:
Dolphin (Mahi Mahi)
Great Barracuda
Response from Captain
August 24, 2025
Thank you, Alex! We’re so glad you and your wife had a blast out there with Tom and Will. The 3/4 day shared trips are a great way to experience offshore fishing in Key West—especially when the crew brings in a haul like that! Glad you enjoyed learning and getting hands-on. We look forward to having you back on board soon.
0
Liz W
Liz W
5.0
Verified
New
Knowledgeable & Personable
1/2 Day Trip – Private Charter - 1:00 PM on December 12, 20252 adults
Capt. Hans and first mate Caleb are a dynamic team! Friendly, very skilled, knowledgeable, take all precautions seriously, and excellent teachers. We caught trophy fish (barracudas) and some tasty yellowtail snapper (upon our request). Definitely will be scheduling a charter again with them 😊
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Reported catch:
Great Barracuda
0
Dillon Tyler
Dillon Tyler
5.0
Verified
Great Service & Fish Caught!
3/4 Day Trip – Shared (PM) on July 5, 20251 adult
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.
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0
Tim Hartka
Tim Hartka
5.0
Verified
Captain and mate getting to know each other
3/4 Day Trip – Shared Charter (AM) on August 7, 20252 adults
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.
Response from Captain
August 24, 2025
Thanks, Tim! We really appreciate you recognizing the effort from Chris and Paul. Every mate starts somewhere, and it’s great to hear they worked as a strong team and delivered a successful day on the water. Glad you got into the Mahis and Bonitas—those are always a favorite on our shared fishing trips here in Key West.
1

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
December 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 $460 
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 $460 
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 $580 
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 $580 
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 $700 
Shared tour: for 2 people
Inshore Shark Trip (3 hrs)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 12:00 PM
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US $650 
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 $650 
Entire boat: up to 6 people
Inshore Shark Trip (3 hrs) - 4:00 PM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 4:00 PM
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US $650 
Entire boat: up to 6 people
1/2 Day Trip – Private Charter
FREE Cancellation 3 days notice
4 Hour Trip, starts at 7:00 AM
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US $1,000 
Entire boat: up to 6 people
1/2 Day Trip – Private Charter - 1:00 PM
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
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US $1,000 
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 $1,000 
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 $1,500 
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 $1,700 
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 $1,900 
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 $2,500 
Entire boat: up to 6 people
There are 29 people looking at this charter.

Customer reviews

Rating summary

4.5/5
out of 5 stars from 405 reviews
Boat
4.4/5
Crew
4.7/5
Experience
4.5/5

Photos & videos by reviewers (367)

amazing time, so much fish!
amazing time, so much fish!
amazing time, so much fish!
+364

Angler rating

279
80
23
11
6

Anglers claimed

Good experience

87%

Appropriate for children

82%

Friendly captain

97%

Satisfied with the boat

91%

Recommend this charter

88%

Caught fish

77%

Showing 1 - 5 of 405 reviews
Showing: 5 of 405 reviews
LORETTA Daniel
LORETTA Daniel
5.0
Verified
New
Difficult week but Cowboy Cowgirl came through
Full Day Trip – Shared Charter on December 15, 20252 adults
We went to Key West just for the fishing trip then wind came up and nothing could go out. They worked with us and took us out our last day. We had hoped for some big boys, sailfish, etc but at this point we just wanted to have fun. The captain Hans managed some rough water and our first mate worked hard to help us all catch fish and that we did. Lots of maceral, snapper and yellow tail and even the odd mutton and blue wrasse. When we got back they were waiting to drive us to the airport to catch our flight. I can't recommend enough how hard they worked to make our trip good and get fish.
0
Alex Moorhead
Alex Moorhead
5.0
Verified
True Key West experience
3/4 Day Trip – Shared Charter (AM) on August 23, 20252 adults
My wife and I went out on Cowboy Cowgirl with Tom and Will and it was a blast. We did the 3/4 day and it was a good amount of fishing time. The ride out to there took about an hour out and back so that’s already leaving you with only 4 hours of fishing time for us and 4 other people. Tom and Will knew a lot about the area and the fish we were looking for. Will guided everyone on what to do and let us learn and experience it ourselves too. We caught a huge haul and Will filleted it and gave us each some to take home. Definitely would recommend! I already plan to come back.
Review media 0
Review media 1
Review media 2
Review media 3
Review media 4
Review media 5
Review media 6
Reported catch:
Dolphin (Mahi Mahi)
Great Barracuda
Response from Captain
August 24, 2025
Thank you, Alex! We’re so glad you and your wife had a blast out there with Tom and Will. The 3/4 day shared trips are a great way to experience offshore fishing in Key West—especially when the crew brings in a haul like that! Glad you enjoyed learning and getting hands-on. We look forward to having you back on board soon.
0
Liz W
Liz W
5.0
Verified
New
Knowledgeable & Personable
1/2 Day Trip – Private Charter - 1:00 PM on December 12, 20252 adults
Capt. Hans and first mate Caleb are a dynamic team! Friendly, very skilled, knowledgeable, take all precautions seriously, and excellent teachers. We caught trophy fish (barracudas) and some tasty yellowtail snapper (upon our request). Definitely will be scheduling a charter again with them 😊
Review media 0
Review media 1
Review media 0
Review media 1
Reported catch:
Great Barracuda
0
Dillon Tyler
Dillon Tyler
5.0
Verified
Great Service & Fish Caught!
3/4 Day Trip – Shared (PM) on July 5, 20251 adult
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
0
Tim Hartka
Tim Hartka
5.0
Verified
Captain and mate getting to know each other
3/4 Day Trip – Shared Charter (AM) on August 7, 20252 adults
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.
Response from Captain
August 24, 2025
Thanks, Tim! We really appreciate you recognizing the effort from Chris and Paul. Every mate starts somewhere, and it’s great to hear they worked as a strong team and delivered a successful day on the water. Glad you got into the Mahis and Bonitas—those are always a favorite on our shared fishing trips here in Key West.
1

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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