Cowboy Cowgirl 36 Ft Hatteras--Since 1965 

4.5/5 (424 reviews)
 1801 N Roosevelt Blvd, Key West, FL 33040, United States

Cowboy Cowgirl 36 Ft Hatteras--Since 1965 

4.5/5 (424 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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Rating

4.5
424 reviews
5
293
4
84
3
24
2
11
1
6
4.4
Boat & equipment
4.7
Captain & crew
4.5
Fishing Experience

Anglers' gallery (379)

great day
Cudas, Yellow Jacks, Mackerals and more!!!
Cudas, Yellow Jacks, Mackerals and more!!!
Cudas, Yellow Jacks, Mackerals and more!!!
Cudas, Yellow Jacks, Mackerals and more!!!
Awesome trip for 5 catching 13 fish!
+373

What anglers say

87%
Great experience
82%
Family friendly
97%
Friendly captain
91%
Good boat
88%
Recommended
77%
Caught fish

All reviews (424)

Filter
Showing 15 of 424 reviews
LORETTA Daniel
LORETTA Daniel
5.0
Verified
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.
Response from Captain
January 18, 2026
Loretta, thank you for the kind words—and for rolling with a windy week. We’re glad we could shift your date and still get you out on your last day. Captain Hans and our first mate work hard to keep things safe, steady, and fun when the weather kicks up, and it’s great to hear everyone hooked fish—mackerel, snapper, yellowtail, even a mutton and blue wrasse. Getting you to the airport on time was the easy part. We appreciate you choosing our Key West fishing charter and hope to chase those “big boys” (including sailfish) with you next time. If you’re planning a return, we run both shared and private charters—pick what fits your group—and we also offer Marquesas Key historical fishing tours for a special day off the beaten path. Also, if you want a keepsake from the trip, 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 happens if wind or weather cancels my trip? A: Safety comes first. We monitor forecasts and, if conditions aren’t safe or enjoyable, we’ll reschedule you to the next safe window or help you choose an alternate trip style that fits the seas. Q: When’s the best time to target sailfish in Key West? A: Late fall through early spring is prime, especially around cold fronts. Tell us your dates and we’ll recommend the best charter (and tactics) to maximize your shot.
0
Curt Weldon
Curt Weldon
5.0
Verified
Great Experience
Half Day Trip – Shared Charter on December 23, 20251 adult
Want to thank the crew of the Sanctuary for providing me with a great experience. My first fishing trip was rescheduled due to rough waters and I went out the very next day. Took us into the Atlantic Ocean, just past the reefs. The crew showed their prowess by getting us on fish right away. Caught many yellow tails, macerals and even a barracuda. We also saw several sharks. This was a once in a lifetime experience for me and it was fantastic. Thank you so much.
Reported catch:
Yellowtail Snapper
Great Barracuda
Response from Captain
January 18, 2026
Curt, thank you for the stellar review and for rolling with the weather call. Safety comes first, and we’re glad we were able to get you back out the very next morning. Hearing that the Sanctuary crew put you right on the bite beyond the reef—yellowtail, mackerel, a toothy barracuda, plus multiple shark sightings—makes our day. That’s a great mixed-bag half-day on a shared charter in Key West, and we’re honored it felt “once in a lifetime.” We’d love to have you back anytime. If you want to focus on big toothy critters next visit, we run dedicated Key West shark fishing adventures (inshore, reef, and deepwater). Or, choose a private charter for a fully customized plan with your own crew and pace. Also, for 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 happens if the forecast looks rough on my day? A: We monitor marine conditions closely. If it’s unsafe or not enjoyable, we’ll reschedule you to the next safe window at no extra charge. Q: What’s the difference between a shared and a private charter? A: Shared trips let solo anglers or small parties split the boat and cost with others—great value and steady action. Private trips reserve the whole boat for your group, with a custom plan (targets, style, pace) and flexibility to change tactics on the fly.
0
Alex Moorhead
Alex Moorhead
5.0
Verified
True Key West experience
3/4 Day Trip – Shared 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.
A group of anglers gathered on a boat, admiring their catch of Mahi Mahi stored in a cooler, showcasing a successful offshore fishing trip.
A large Mahi Mahi is displayed on a catch board while anglers prepare their catch on the dock after a successful fishing trip.
A proud angler displaying a large Mahi Mahi at the dock, surrounded by a catch of smaller fish after a successful fishing trip.
A proud angler displaying a large Mahi Mahi on a fishing boat, enjoying a successful day out on the water.
Angler proudly displaying a large Mahi Mahi while fishing offshore, showcasing the excitement of a successful catch.
A fishing charter boat named 'Cow Girl' docked at the marina, with a crew member preparing the vessel for the day.
A variety of fish including Mahi Mahi and Barracuda laid out on a dock after a successful fishing trip in Key West, FL.
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
Danielle Creamer
Danielle Creamer
4.3
Verified
4 hour turned 6 hour morning trip
Half Day Trip – Shared Charter on March 1, 20262 adults
We booked the 4 hour morning shared charter. This has nothing to do with the captain and mate, but the trip ended up being shared with people who had booked 6 hour trips. We were grateful for the extra 2 hours that we had on the boat but just wished we had been told in advance as we had to try to cancel plans with minimal cell service when we figured out that we wouldnt be back by 12 PM. Again, more of an issue with the booking company it seems, and we were grateful for the time - just wish the company had communicated this. Unfortunately didn’t catch a lot of fish which happens! We had leas fishing experience than the other people on the boat, but Captain Bobby and first mate CJ were great and helped us make the most of the trip!
Reported catch:
Great Barracuda
Yellowtail Snapper
Response from Captain
March 27, 2026
Thank you Danielle for your thoughtful review—we really appreciate you taking the time to share your experience. we truly appreciate your recommendation We’re glad to hear you enjoyed the crew and that they helped make the most of the trip for you—that’s always our goal. We do apologize for the confusion on the trip length. Occasionally with shared charters, bookings from different platforms can get combined, and in this case it resulted in a longer trip than expected. While we’re glad you were able to enjoy the extra time on the water, we completely understand how not knowing in advance can affect your plans, and that’s something we are continuing to work on improving with communication. As you mentioned, fishing can be hit or miss, but we’re happy the crew worked hard to give you the best opportunity possible.
0
Roberta Townsend
Roberta Townsend
5.0
Verified
Irish Cowboy 3/4 day trip
3/4 Day Trip – Shared on May 31, 20252 adults
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!
An angler actively reeling in a fish while fishing on a charter boat in clear blue waters.
Two anglers celebrating a successful catch aboard a fishing boat, showcasing a freshly caught fish in the open ocean.
Reported catch:
Cero Mackerel
Dolphin (Mahi Mahi)
Response from Captain
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!
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
April 2026
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Number of days
1
Group Size
2 adults • 0 children
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Half Day Trip – Shared Charter
FREE Cancellation 3 days notice
4 Hour Trip
starts at 8:00 AM
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US $460
Shared tour: 2 people
Half Day Trip – Shared Charter - 1:00 PM
FREE Cancellation 3 days notice
4 Hour Trip
starts at 1:00 PM
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US $460
Shared tour: 2 people
3/4 Day Trip – Shared
FREE Cancellation 3 days notice
6 Hour Trip
starts at 8:00 AM
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US $580
Shared tour: 2 people
3/4 Day Trip – Shared - 1:00 PM
FREE Cancellation 3 days notice
6 Hour Trip
starts at 1:00 PM
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US $580
Shared tour: 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: 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) - 2:00 PM
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 16 people looking at this charter.

Rating

4.5
424 reviews
5
293
4
84
3
24
2
11
1
6
4.4
Boat & equipment
4.7
Captain & crew
4.5
Fishing Experience

Anglers' gallery (379)

great day
Cudas, Yellow Jacks, Mackerals and more!!!
Cudas, Yellow Jacks, Mackerals and more!!!
Cudas, Yellow Jacks, Mackerals and more!!!
Cudas, Yellow Jacks, Mackerals and more!!!
Awesome trip for 5 catching 13 fish!
+373

What anglers say

87%
Great experience
82%
Family friendly
97%
Friendly captain
91%
Good boat
88%
Recommended
77%
Caught fish

All reviews (424)

Filter
Showing 15 of 424 reviews
LORETTA Daniel
LORETTA Daniel
5.0
Verified
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.
Response from Captain
January 18, 2026
Loretta, thank you for the kind words—and for rolling with a windy week. We’re glad we could shift your date and still get you out on your last day. Captain Hans and our first mate work hard to keep things safe, steady, and fun when the weather kicks up, and it’s great to hear everyone hooked fish—mackerel, snapper, yellowtail, even a mutton and blue wrasse. Getting you to the airport on time was the easy part. We appreciate you choosing our Key West fishing charter and hope to chase those “big boys” (including sailfish) with you next time. If you’re planning a return, we run both shared and private charters—pick what fits your group—and we also offer Marquesas Key historical fishing tours for a special day off the beaten path. Also, if you want a keepsake from the trip, 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 happens if wind or weather cancels my trip? A: Safety comes first. We monitor forecasts and, if conditions aren’t safe or enjoyable, we’ll reschedule you to the next safe window or help you choose an alternate trip style that fits the seas. Q: When’s the best time to target sailfish in Key West? A: Late fall through early spring is prime, especially around cold fronts. Tell us your dates and we’ll recommend the best charter (and tactics) to maximize your shot.
0
Curt Weldon
Curt Weldon
5.0
Verified
Great Experience
Half Day Trip – Shared Charter on December 23, 20251 adult
Want to thank the crew of the Sanctuary for providing me with a great experience. My first fishing trip was rescheduled due to rough waters and I went out the very next day. Took us into the Atlantic Ocean, just past the reefs. The crew showed their prowess by getting us on fish right away. Caught many yellow tails, macerals and even a barracuda. We also saw several sharks. This was a once in a lifetime experience for me and it was fantastic. Thank you so much.
Reported catch:
Yellowtail Snapper
Great Barracuda
Response from Captain
January 18, 2026
Curt, thank you for the stellar review and for rolling with the weather call. Safety comes first, and we’re glad we were able to get you back out the very next morning. Hearing that the Sanctuary crew put you right on the bite beyond the reef—yellowtail, mackerel, a toothy barracuda, plus multiple shark sightings—makes our day. That’s a great mixed-bag half-day on a shared charter in Key West, and we’re honored it felt “once in a lifetime.” We’d love to have you back anytime. If you want to focus on big toothy critters next visit, we run dedicated Key West shark fishing adventures (inshore, reef, and deepwater). Or, choose a private charter for a fully customized plan with your own crew and pace. Also, for 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 happens if the forecast looks rough on my day? A: We monitor marine conditions closely. If it’s unsafe or not enjoyable, we’ll reschedule you to the next safe window at no extra charge. Q: What’s the difference between a shared and a private charter? A: Shared trips let solo anglers or small parties split the boat and cost with others—great value and steady action. Private trips reserve the whole boat for your group, with a custom plan (targets, style, pace) and flexibility to change tactics on the fly.
0
Alex Moorhead
Alex Moorhead
5.0
Verified
True Key West experience
3/4 Day Trip – Shared 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.
A group of anglers gathered on a boat, admiring their catch of Mahi Mahi stored in a cooler, showcasing a successful offshore fishing trip.
A large Mahi Mahi is displayed on a catch board while anglers prepare their catch on the dock after a successful fishing trip.
A proud angler displaying a large Mahi Mahi at the dock, surrounded by a catch of smaller fish after a successful fishing trip.
A proud angler displaying a large Mahi Mahi on a fishing boat, enjoying a successful day out on the water.
Angler proudly displaying a large Mahi Mahi while fishing offshore, showcasing the excitement of a successful catch.
A fishing charter boat named 'Cow Girl' docked at the marina, with a crew member preparing the vessel for the day.
A variety of fish including Mahi Mahi and Barracuda laid out on a dock after a successful fishing trip in Key West, FL.
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
Danielle Creamer
Danielle Creamer
4.3
Verified
4 hour turned 6 hour morning trip
Half Day Trip – Shared Charter on March 1, 20262 adults
We booked the 4 hour morning shared charter. This has nothing to do with the captain and mate, but the trip ended up being shared with people who had booked 6 hour trips. We were grateful for the extra 2 hours that we had on the boat but just wished we had been told in advance as we had to try to cancel plans with minimal cell service when we figured out that we wouldnt be back by 12 PM. Again, more of an issue with the booking company it seems, and we were grateful for the time - just wish the company had communicated this. Unfortunately didn’t catch a lot of fish which happens! We had leas fishing experience than the other people on the boat, but Captain Bobby and first mate CJ were great and helped us make the most of the trip!
Reported catch:
Great Barracuda
Yellowtail Snapper
Response from Captain
March 27, 2026
Thank you Danielle for your thoughtful review—we really appreciate you taking the time to share your experience. we truly appreciate your recommendation We’re glad to hear you enjoyed the crew and that they helped make the most of the trip for you—that’s always our goal. We do apologize for the confusion on the trip length. Occasionally with shared charters, bookings from different platforms can get combined, and in this case it resulted in a longer trip than expected. While we’re glad you were able to enjoy the extra time on the water, we completely understand how not knowing in advance can affect your plans, and that’s something we are continuing to work on improving with communication. As you mentioned, fishing can be hit or miss, but we’re happy the crew worked hard to give you the best opportunity possible.
0
Roberta Townsend
Roberta Townsend
5.0
Verified
Irish Cowboy 3/4 day trip
3/4 Day Trip – Shared on May 31, 20252 adults
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!
An angler actively reeling in a fish while fishing on a charter boat in clear blue waters.
Two anglers celebrating a successful catch aboard a fishing boat, showcasing a freshly caught fish in the open ocean.
Reported catch:
Cero Mackerel
Dolphin (Mahi Mahi)
Response from Captain
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!
0

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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What’s biting in Key West right now

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