Cowboy Cowgirl Sportfishing – Cowgirl II 

4.7/5 (25 reviews)
 5950 Peninsular Avenue, Stock Island, FL 33040, United States

Cowboy Cowgirl Sportfishing – Cowgirl II 

4.7/5 (25 reviews)
map-thumbnail
5950 Peninsular Avenue
Stock Island, FL, United States

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 many boats at their disposal, they can offer inshore/offshore fishing trips to suit every type of angler.

Cowgirl II is a well-appointed 38’ Hatteras sport fishing boat equipped for light tackle fishing.  A very comfortable ride for groups of up to 6 people plus the crew. The boat features a head, as well as outriggers, downriggers, and lots of inside comfortable seating. With a large deck area, everyone will be able to get involved in the fishing action.

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 waters, providing all the know-how and equipment you need to catch species such as Mahi Mahi, Sailfish, Marlin, Wahoo, and many more. Cowboy Cowgirl Sportfishing 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 our other boat options. You won’t regret it!

Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading

Customer reviews

Rating summary

4.7/5
out of 5 stars from 25 reviews
Boat
4.6/5
Crew
4.9/5
Experience
4.7/5

Photos & videos by reviewers (30)

Yellowtail and a grouper
Yellowtail and a grouper
Wonderful successful trip!
+27

Angler rating

21
2
2
0
0

Anglers claimed

Good experience

95%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

94%

Recommend this charter

92%

Caught fish

96%

Showing 1 - 5 of 25 reviews
Showing: 5 of 25 reviews
Kacey D.
Kacey D.
5.0/5

Mar 22, 2025

Half Day Trip Inshore (PM)

Yellowtail and a grouper

VERIFIED

Had such a great trip out on the Irish cowboy… captain Bobby and Jace were great with me and my boys. Will hopefully be able to return and go out again.

Had such a great trip out on the Irish cowboy… captain Bobby and Jace were great with me and my boys. Will hopefully be able to...  

Review media 0
Review media 1
 Kacey D. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

1 person finds this review helpful
 Kacey D. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

1 person finds this review helpful

Brian M.
Brian M.
4.7/5

Nov 22, 2024

Half Day Trip (AM) Inshore

Wonderful successful trip!

VERIFIED

The crew was very knowledgeable. Tried several tactics to find fish. Very polite and accommodating. The owners were very communicative and in touch from the reservation forward. I would highly recommend! Cannot wait to return next year.

The crew was very knowledgeable. Tried several tactics to find fish. Very polite and accommodating. The owners were very communicative...  

Review media 0
Review media 1
Review media 1
Captain replied
 Brian M. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

 Brian M. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

undefined (The Captain)
Replied on December 17, 2024
Thank you so much for the wonderful review, Brian! We’re thrilled to hear that you and your group had a successful and enjoyable time aboard the *Cowgirl II*. It’s great to know that our crew’s knowledge and tactics helped you find fish, and that everyone was polite and accommodating throughout the day. We truly appreciate your kind words about our communication and are glad to have made your fishing trip a memorable one. We can’t wait to welcome you back next year for more fantastic Key West fishing adventures!

Jason D.
Jason D.
5.0/5

Feb 8, 2025

Deep Water Shark Fishing Trip (AM)

Fantastic 1st mate

VERIFIED

First 4 dish we caught were all sharks

First 4 dish we caught were all sharks  

Captain replied
 Jason D. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

1 person finds this review helpful
 Jason D. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

1 person finds this review helpful
undefined (The Captain)
Replied on February 8, 2025
Thank you, Jason! We’re thrilled you had an awesome time on your deepwater shark fishing adventure! 🦈 Landing four sharks right off the bat is an adrenaline rush, and we’re glad our first mate made the experience even better. We appreciate your recommendation and can’t wait to have you back for another action-packed trip! If you’re ever looking to mix things up, we also offer private and shared charters, fishing and sandbar combo trips, and even a Marquesas Key historical fishing tour for a unique experience. And don’t forget to grab a Cowboy Cowgirl Sportfishing t-shirt to remember your trip. You can purchase your T-shirts BiteBackBrand under local legends we are listed on there for all your T-shirt. Needs . Hope to see you back on the water soon!”

Daniel Y.
Daniel Y.
5.0/5

Jun 7, 2024

Half Day Trip (AM) Inshore

Father and son trip

VERIFIED

My son and I had a fantastic time on the Cowgirl II with Cowboy Cowgirl Sportfishing. The crew's expertise made our fishing trip unforgettable. They guided us to plentiful waters, where we reeled in some impressive catches with their help. The friendly and enthusiastic atmosphere on board added to the excitement. We left with cherished memories and a desire to return for another adventure. If you're seeking a top-notch fishing experience with a skilled and welcoming crew, look no further than Cowboy Cowgirl Sportfishing – you won't be disappointed.

My son and I had a fantastic time on the Cowgirl II with Cowboy Cowgirl Sportfishing. The crew's expertise made our fishing trip...  

Review media 0
Captain replied
 Daniel Y. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

 Daniel Y. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

undefined (The Captain)
Replied on June 22, 2024
Thank you so much for the glowing review! We're thrilled to hear that you and your son had a fantastic time on the Cowgirl II with our Cowboy Cowgirl Sportfishing crew. It's wonderful to know that their expertise helped make your trip unforgettable and that you enjoyed both the fishing and the atmosphere onboard. We appreciate your high praise and are delighted that you're already thinking about your next adventure with us. Looking forward to welcoming you back for more top-notch fishing experiences in Key West!

Robert B.
Robert B.
5.0/5

Jul 6, 2023

Half Day Trip (AM) Inshore

Fishing with John Mark & Michelle

VERIFIED

 

Captain replied
 Robert B. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

2 persons find this review helpful
 Robert B. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

2 persons find this review helpful
undefined (The Captain)

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
September 2025
SuMoTuWeThFrSa
Loading...
Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Inshore Shark Fishing Trip (AM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 8:00 AM
Loading...
US $600 
Entire boat: up to 6 people
Inshore Shark Fishing Trip (PM)
FREE Cancellation 3 days notice
3 Hour Trip, starts at 1:00 PM
Loading...
US $600 
Entire boat: up to 6 people
Deep Water Shark Fishing Trip (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
Loading...
US $750 
Entire boat: up to 6 people
Half Day Trip (AM) Inshore
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
Loading...
US $750 
Entire boat: up to 6 people
Half Day – Deep Water Shark (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
Loading...
US $750 
Entire boat: up to 6 people
Half Day Trip Inshore (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
Loading...
US $750 
Entire boat: up to 6 people
3/4 Day Trip (AM) Inshore
FREE Cancellation 3 days notice
6 Hour Trip, starts at 8:00 AM
Loading...
US $1,050 
Entire boat: up to 6 people
3/4 Day Trip Inshore (PM)
FREE Cancellation 3 days notice
6 Hour Trip, starts at 12:00 PM
Loading...
US $1,050 
Entire boat: up to 6 people
Full Day Trip Shark Fishing
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
Loading...
US $1,350 
Entire boat: up to 6 people

Customer reviews

Rating summary

4.7/5
out of 5 stars from 25 reviews
Boat
4.6/5
Crew
4.9/5
Experience
4.7/5

Photos & videos by reviewers (30)

Yellowtail and a grouper
Yellowtail and a grouper
Wonderful successful trip!
+27

Angler rating

21
2
2
0
0

Anglers claimed

Good experience

95%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

94%

Recommend this charter

92%

Caught fish

96%

Showing 1 - 5 of 25 reviews
Showing: 5 of 25 reviews
Kacey D.
Kacey D.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Yellowtail and a grouper

VERIFIED

Half Day Trip Inshore (PM) on March 22, 2025

Had such a great trip out on the Irish cowboy… captain Bobby and Jace were great with me and my boys. Will hopefully be able to return and go out again.

Had such a great trip out on the Irish cowboy… captain Bobby and Jace were great with me and my boys. Will hopefully be able to return and go out again.  

Review media 0
Review media 1
 Kacey D. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

1 person finds this review helpful

Brian M.
Brian M.
4.7/5

Experience:

4.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Wonderful successful trip!

VERIFIED

Half Day Trip (AM) Inshore on November 22, 2024

The crew was very knowledgeable. Tried several tactics to find fish. Very polite and accommodating. The owners were very communicative and in touch from the reservation forward. I would highly recommend! Cannot wait to return next year.

The crew was very knowledgeable. Tried several tactics to find fish. Very polite and accommodating. The owners were very communicative and in touch from the reservation forward. I would highly recommend! Cannot wait to return next year.  

Review media 0
Review media 1
Review media 1
 Brian M. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

undefined (The Captain)
Replied on December 17, 2024
Thank you so much for the wonderful review, Brian! We’re thrilled to hear that you and your group had a successful and enjoyable time aboard the *Cowgirl II*. It’s great to know that our crew’s knowledge and tactics helped you find fish, and that everyone was polite and accommodating throughout the day. We truly appreciate your kind words about our communication and are glad to have made your fishing trip a memorable one. We can’t wait to welcome you back next year for more fantastic Key West fishing adventures!

Jason D.
Jason D.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Fantastic 1st mate

VERIFIED

Deep Water Shark Fishing Trip (AM) on February 8, 2025

First 4 dish we caught were all sharks

First 4 dish we caught were all sharks  

 Jason D. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

1 person finds this review helpful
undefined (The Captain)
Replied on February 8, 2025
Thank you, Jason! We’re thrilled you had an awesome time on your deepwater shark fishing adventure! 🦈 Landing four sharks right off the bat is an adrenaline rush, and we’re glad our first mate made the experience even better. We appreciate your recommendation and can’t wait to have you back for another action-packed trip! If you’re ever looking to mix things up, we also offer private and shared charters, fishing and sandbar combo trips, and even a Marquesas Key historical fishing tour for a unique experience. And don’t forget to grab a Cowboy Cowgirl Sportfishing t-shirt to remember your trip. You can purchase your T-shirts BiteBackBrand under local legends we are listed on there for all your T-shirt. Needs . Hope to see you back on the water soon!”

Daniel Y.
Daniel Y.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Father and son trip

VERIFIED

Half Day Trip (AM) Inshore on June 7, 2024

My son and I had a fantastic time on the Cowgirl II with Cowboy Cowgirl Sportfishing. The crew's expertise made our fishing trip unforgettable. They guided us to plentiful waters, where we reeled in some impressive catches with their help. The friendly and enthusiastic atmosphere on board added to the excitement. We left with cherished memories and a desire to return for another adventure. If you're seeking a top-notch fishing experience with a skilled and welcoming crew, look no further than Cowboy Cowgirl Sportfishing – you won't be disappointed.

My son and I had a fantastic time on the Cowgirl II with Cowboy Cowgirl Sportfishing. The crew's expertise made our fishing trip unforgettable. They guided us to plentiful waters, where we reeled in some impressive catches with their help. The friendly and enthusiastic atmosphere on board added to the excitement. We left with cherished memories and a desire to return for another adventure. If you're seeking a top-notch fishing experience with a skilled and welcoming crew, look no further than...  

Review media 0
 Daniel Y. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

undefined (The Captain)
Replied on June 22, 2024
Thank you so much for the glowing review! We're thrilled to hear that you and your son had a fantastic time on the Cowgirl II with our Cowboy Cowgirl Sportfishing crew. It's wonderful to know that their expertise helped make your trip unforgettable and that you enjoyed both the fishing and the atmosphere onboard. We appreciate your high praise and are delighted that you're already thinking about your next adventure with us. Looking forward to welcoming you back for more top-notch fishing experiences in Key West!

Robert B.
Robert B.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Fishing with John Mark & Michelle

VERIFIED

Half Day Trip (AM) Inshore on July 6, 2023

 

 Robert B. recommends Cowboy Cowgirl Sportfishing – Cowgirl II

Mark review as helpful

2 persons find this review helpful
undefined (The Captain)

FAQs about Cowboy Cowgirl Sportfishing – Cowgirl II

Loading
Loading
Loading
Loading
Loading
Loading
Loading

The fish you can target

Loading
Loading
Loading
Loading
Loading

What is the boat like?

Boat Image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
36 ft
Year built
1969
Restored in
2021
Boat manufacturer
Hatteras
Boat type
Sportfishing

Engine model
Detroit
Powered by
2 x 325HP
Max cruising speed
18 knots
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading

What’s biting in Stock Island right now

Loading

Compare similar fishing charters

Loading...
Loading...
Loading...