Cowboy Cowgirl Charters – Irish Cowboy 

4.6/5 (115 reviews)
 1801 North Roosevelt Boulevard, Key West, FL 33040, United States

Cowboy Cowgirl Charters – Irish Cowboy 

4.6/5 (115 reviews)
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1801 North Roosevelt Boulevard
Key West, FL, United States

If you're looking for a charter that can cater to both families with kids going out for the first time, as well as a group of experienced sea wolves looking to tick off a catch from their bucket list, Cowboy Charters has you covered. Their goal is for you to have an exciting, memorable, and fun-filled journey every time you leave the dock and come back with a huge smile!

Join the captain on board their 40' flybridge, manufactured by the famous Luhrs company and restored in 2018. You can expect all the modern amenities and comforts on the 'Irish Cowboy'. A full-head toilet, showers, and a bed are available so you can take a break from fighting the gorgeous fish. The Irish Cowboy hasn't skimped on serious fishing equipment either, a flybridge, outriggers and downriggers, as well as a fighting chair, are all available on board to give you an added edge in getting that dream fish.

With Capt. Tim you will target a variety of excellent species in the area. Get ready to fight Blue and White Marlins, Mahi Mahi, Sailfish, Kingfish, Groupers, Blackfin Tunas, Wahoos, Snappers, Tilefish, Sharks, and anything else you run into! You'll get the chance to try out many different techniques, such as spinning, jigging, trolling, bottom fishing, or drift fishing with light and heavy tackle. For the adventurous anglers, kite fishing is also available, perfect for going after Marlins.

The first mate will assist you in any way possible, as well as clean and fillet your catch. Gratuity for the crew is appreciated, with 20% being the local norm. All required equipment will be supplied by the charter. There's no minimum age for kids with Cowboy Charters and anglers of all ages and skill levels are invited to join them on an exciting offshore adventure!

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Rating

4.6
115 reviews
5
88
4
17
3
2
2
4
1
2
4.4
Boat & equipment
4.8
Captain & crew
4.6
Fishing Experience

Anglers' gallery (86)

3/4 Day with Captain Cole
Sailfish and mahi
Sailfish and mahi
A group of anglers, including children, proudly displaying a large Sailfish on a fishing boat, showcasing a successful deep-sea fishing trip.
Real Florida fishing
Amazing Day with Cowgirl sports fishing charters
+80

What anglers say

94%
Great experience
91%
Family friendly
99%
Friendly captain
93%
Good boat
92%
Recommended
82%
Caught fish

All reviews (115)

Filter
Showing 15 of 115 reviews
Pryor Brenner
Pryor Brenner
5.0
Verified
Anglers young and old
Full Day Trip on December 27, 20254 adults2 children
Amazing experience with this charter. They c ustomized a trip for little ones to catch some bait fish and then swapped out for older anglers and some bigger game fish. Frank and Will were an awesome team and got us on fish early and worked hard to keep the rods bent and the lines tight. Total professionals and highly recommended. Enjoying fresh grouper tacos as I write this review!
Reported catch:
Black Grouper
King Mackerel (Kingfish)
Response from Captain
January 18, 2026
Pryor, thank you for the outstanding review and for trusting us with a full-day on the Irish Cowboy. Love hearing the plan worked—starting the little ones on steady bait action, then shifting gears so the older anglers could tangle with bigger game. Capt. Frank and Mate Will pride themselves on keeping the rods bent and the boat organized so families can just fish and have fun. Fresh grouper tacos afterward is exactly how we like to see the day end! Next time you’re back, we can tailor another private charter for the whole crew—or, if you want a different kind of thrill, our shark adventures (inshore, reef, or deepwater) are a blast. And if you want to mix it up, we also run fishing & sandbar combo trips to cool off at the islands after the bite. Also, if you want a keepsake from the day, go to BiteBackBrand and under Local Legends, go to Cowboy to get your t-shirts and other gear. —Michelle & the Cowboy Cowgirl Sportfishing team Helpful Q&A Q: What’s the best trip for families with mixed ages/experience? A: A 4–8 hour private charter lets us start with easy action (bait, snapper, jacks) and then step up to larger targets as attention spans and conditions allow. Tell us your goals and we’ll build the day around them. Q: Can we keep fish and have it cooked locally? A: Yes—within Florida regs. We’ll fillet your catch at the dock and recommend nearby “cook-your-catch” restaurants so dinner is handled.
1
John Freiler
John Freiler
Fort Myers, FL
5.0
Verified
Sailfish and mahi
3/4 Day Trip (PM) on July 1, 20232 adults4 children
Captian Chris and mate Will knew right where to go. They were dialed in to the fish and very knowledgeable about the waters. They put us on fish early and often on our 6hr charter. We caught so many mahi we told them to start throwing them back because we already had enough to eat. Will kept the baits fresh and worked the entire trip making sure the gear was ready for the big one. Which Capt. Chris found us in the last hour of the trip, a beautiful Key West sailfish! I would recommend this charter to anyone and will book again next time we are down.
Review media 0
Review media 1
A group of anglers, including children, proudly displaying a large Sailfish on a fishing boat, showcasing a successful deep-sea fishing trip.
Reported catch:
Dolphin (Mahi Mahi)
Sailfish
0
Kelsey Green
Kelsey Green
Dallas, TX
5.0
Verified
Mahi Mahi, snowy grouper, silk snapper
Full Day Trip on May 28, 20224 adults
These guys are so good at what they do!! We did not go fishing - we went CATCHING!! I can’t say enough about Captain Pel & 1st Mate John giving us the best experience and showing us all the fishing techniques!!! From departure to return, these guys have it down to an art and know where the fish are!! I can’t recommend them enough. If we come back, we know who we are calling!! Thanks Pel & John for the BEST fishing trip and sending us back to TX with a freezer full of fish!! True fishing masters!
Review media 0
1
Jaime Machimbarrena
Jaime Machimbarrena
5.0
Verified
March fishing trip
Half Day Trip (PM) on March 24, 20256 adults
Reported catch:
King Mackerel (Kingfish)
0
Maria Bravo
Maria Bravo
Boynton Beach, Florida
5.0
Amazing Day with Cowgirl sports fishing charters
Half Day Trip (PM) on October 22, 2022
Incredible day out on the water! My daughter and I went off shore fishing there was some wind but the boat was big enough to handle to waves, the captain called it “sporty” and I must agree. I was so impressed that my 5 year daughter did not get sea sick. I think I’ll make this a yearly tradition! Thank you to the captain and mate for this pleasant experience. Key West has definitely been a bucket list vacation for me and it did not disappoint.
Review media 0
0

Trip availability and prices

Trip Date:
Days:
Group Size:
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April 2026
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Number of days
1
Group Size
2 adults • 0 children
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Half Day Trip (AM)
FREE Cancellation 3 days notice
4 Hour Trip
starts at 7:00 AM
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US $1,100
Entire boat: up to 6 people
Half Day Trip (PM)
FREE Cancellation 3 days notice
4 Hour Trip
starts at 1:00 PM
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US $1,100
Entire boat: up to 6 people
3/4 Day Trip (AM)
FREE Cancellation 3 days notice
6 Hour Trip
starts at 7:00 AM
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US $1,400
Entire boat: up to 6 people
3/4 Day Trip (PM)
FREE Cancellation 3 days notice
6 Hour Trip
starts at 1:00 PM
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US $1,400
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 3 days notice
8 Hour Trip
starts at 7:00 AM
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US $1,600
Entire boat: up to 6 people
Extended Full Day Trip
FREE Cancellation 3 days notice
12 Hour Trip
starts at 7:00 AM
US $2,000
Entire boat: up to 6 people
There are 5 people looking at this charter.

Rating

4.6
115 reviews
5
88
4
17
3
2
2
4
1
2
4.4
Boat & equipment
4.8
Captain & crew
4.6
Fishing Experience

Anglers' gallery (86)

3/4 Day with Captain Cole
Sailfish and mahi
Sailfish and mahi
A group of anglers, including children, proudly displaying a large Sailfish on a fishing boat, showcasing a successful deep-sea fishing trip.
Real Florida fishing
Amazing Day with Cowgirl sports fishing charters
+80

What anglers say

94%
Great experience
91%
Family friendly
99%
Friendly captain
93%
Good boat
92%
Recommended
82%
Caught fish

All reviews (115)

Filter
Showing 15 of 115 reviews
Pryor Brenner
Pryor Brenner
5.0
Verified
Anglers young and old
Full Day Trip on December 27, 20254 adults2 children
Amazing experience with this charter. They c ustomized a trip for little ones to catch some bait fish and then swapped out for older anglers and some bigger game fish. Frank and Will were an awesome team and got us on fish early and worked hard to keep the rods bent and the lines tight. Total professionals and highly recommended. Enjoying fresh grouper tacos as I write this review!
Reported catch:
Black Grouper
King Mackerel (Kingfish)
Response from Captain
January 18, 2026
Pryor, thank you for the outstanding review and for trusting us with a full-day on the Irish Cowboy. Love hearing the plan worked—starting the little ones on steady bait action, then shifting gears so the older anglers could tangle with bigger game. Capt. Frank and Mate Will pride themselves on keeping the rods bent and the boat organized so families can just fish and have fun. Fresh grouper tacos afterward is exactly how we like to see the day end! Next time you’re back, we can tailor another private charter for the whole crew—or, if you want a different kind of thrill, our shark adventures (inshore, reef, or deepwater) are a blast. And if you want to mix it up, we also run fishing & sandbar combo trips to cool off at the islands after the bite. Also, if you want a keepsake from the day, go to BiteBackBrand and under Local Legends, go to Cowboy to get your t-shirts and other gear. —Michelle & the Cowboy Cowgirl Sportfishing team Helpful Q&A Q: What’s the best trip for families with mixed ages/experience? A: A 4–8 hour private charter lets us start with easy action (bait, snapper, jacks) and then step up to larger targets as attention spans and conditions allow. Tell us your goals and we’ll build the day around them. Q: Can we keep fish and have it cooked locally? A: Yes—within Florida regs. We’ll fillet your catch at the dock and recommend nearby “cook-your-catch” restaurants so dinner is handled.
1
John Freiler
John Freiler
Fort Myers, FL
5.0
Verified
Sailfish and mahi
3/4 Day Trip (PM) on July 1, 20232 adults4 children
Captian Chris and mate Will knew right where to go. They were dialed in to the fish and very knowledgeable about the waters. They put us on fish early and often on our 6hr charter. We caught so many mahi we told them to start throwing them back because we already had enough to eat. Will kept the baits fresh and worked the entire trip making sure the gear was ready for the big one. Which Capt. Chris found us in the last hour of the trip, a beautiful Key West sailfish! I would recommend this charter to anyone and will book again next time we are down.
Review media 0
Review media 1
A group of anglers, including children, proudly displaying a large Sailfish on a fishing boat, showcasing a successful deep-sea fishing trip.
Reported catch:
Dolphin (Mahi Mahi)
Sailfish
0
Kelsey Green
Kelsey Green
Dallas, TX
5.0
Verified
Mahi Mahi, snowy grouper, silk snapper
Full Day Trip on May 28, 20224 adults
These guys are so good at what they do!! We did not go fishing - we went CATCHING!! I can’t say enough about Captain Pel & 1st Mate John giving us the best experience and showing us all the fishing techniques!!! From departure to return, these guys have it down to an art and know where the fish are!! I can’t recommend them enough. If we come back, we know who we are calling!! Thanks Pel & John for the BEST fishing trip and sending us back to TX with a freezer full of fish!! True fishing masters!
Review media 0
1
Jaime Machimbarrena
Jaime Machimbarrena
5.0
Verified
March fishing trip
Half Day Trip (PM) on March 24, 20256 adults
Reported catch:
King Mackerel (Kingfish)
0
Maria Bravo
Maria Bravo
Boynton Beach, Florida
5.0
Amazing Day with Cowgirl sports fishing charters
Half Day Trip (PM) on October 22, 2022
Incredible day out on the water! My daughter and I went off shore fishing there was some wind but the boat was big enough to handle to waves, the captain called it “sporty” and I must agree. I was so impressed that my 5 year daughter did not get sea sick. I think I’ll make this a yearly tradition! Thank you to the captain and mate for this pleasant experience. Key West has definitely been a bucket list vacation for me and it did not disappoint.
Review media 0
0

FAQs about Cowboy Cowgirl Charters – Irish Cowboy

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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
40 ft
Year built
2005
Restored in
2018
Boat manufacturer
Luhrs
Boat type
Sportfishing

Engine model
Caterpillar
Powered by
2 x 750HP
Max cruising speed
21 knots
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