Cowboy Cowgirl Sportfishing – Cowgirl II

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!



Trip availability and prices

  • Private trip
    Inshore Shark Fishing Trip (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    Price for up to 6 persons
    US $600
    Inshore shark fishing is an exciting experience that can push even the most seasoned anglers to their limits! With the right equipment, you'll be abe to find plenty of sharks in the calm, shallow waters. Light tackle can make the challenge even more thrilling, as you'll need to work extra hard to land one of these powerful creatures. We always practice safe fishing techniques. Good luck, and tight lines!
    Targeted fish
    Shark (Hammerhead)
    Hammerhead Shark
    Shark (Blacktip)
    Blacktip Shark
    Shark (Tiger)
    Tiger Shark
    Shark (Nurse)
    Nurse Shark
    Shark (Bull)
    Bull Shark
    Shark (Lemon)
    Lemon Shark
  • Private trip
    Inshore Shark Fishing Trip (PM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    Price for up to 6 persons
    US $600
    Inshore shark fishing is an exciting experience that can push even the most seasoned anglers to their limits! With the right equipment, you'll be abe to find plenty of sharks in the calm, shallow waters. Light tackle can make the challenge even more thrilling, as you'll need to work extra hard to land one of these powerful creatures. We always practice safe fishing techniques. Good luck, and tight lines!
    Targeted fish
    Shark (Hammerhead)
    Hammerhead Shark
    Shark (Blacktip)
    Blacktip Shark
    Shark (Tiger)
    Tiger Shark
    Shark (Nurse)
    Nurse Shark
    Shark (Bonnethead)
    Bonnethead Shark
    Shark (Bull)
    Bull Shark
    Shark (Lemon)
    Lemon Shark
  • Private trip
    Deep Water Shark Fishing Trip (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    Price for up to 6 persons
    US $750
    Deepwater shark fishing is an exciting way to experience the ocean's depts. Depending on the sharks you're targeting, you may want to choose either light or heavy tackle. Light tackle is best for smaller sharks and will give you a more challenging fight, while heavy tackle is more suitable for larger sharks. The structure is also important when Captain is considering the type of tackle to be used. Sharks on wrecks tend to be a bit larger than those inshore.
    Targeted fish
    Shark (Hammerhead)
    Hammerhead Shark
    Shark (Blacktip)
    Blacktip Shark
    Shark (Tiger)
    Tiger Shark
    Shark (Nurse)
    Nurse Shark
    Shark (Bull)
    Bull Shark
    Shark (Lemon)
    Lemon Shark
  • Private trip
    Half Day Trip (AM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 8:00 AM
    Price for up to 6 persons
    US $750
    Thank your for your request! There will be a $150 fuel surcharge due at thevdock. We would be delighted to arrange a 4-hours fishing trip for. you. Our captain is knowledgeable and will be able to advise you on the best target fish depending on weather conditions. We will always try to fulfill. your request, and ensure that you have a productive and enjoyable day. Please let us know if you have any questions or special request and we will do our best to accommodate you. Thank you again for choosing us!
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Amberjack
    Amberjack
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Marlin (Blue)
    Blue Marlin
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Grouper (Black)
    Black Grouper
    Shark (Hammerhead)
    Hammerhead Shark
    Tuna (Blackfin)
    Blackfin Tuna
    Bonito
    Bonito
    Shark (Bull)
    Bull Shark
    Cero Mackerel
    Cero Mackerel
  • Private trip
    Half Day – Deep Water Shark (PM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    Price for up to 6 persons
    US $750
    Deepwater shark fishing is an exciting way to experience the ocean's depts. Depending on the sharks you're targeting, you may want to choose either light or heavy tackle. Light tackle is best for smaller sharks and will give you a more challenging fight, while heavy tackle is more suitable for larger sharks. The structure is also important when Captain is considering the type of tackle to be used. Sharks on wrecks tend to be a bit larger than those inshore.
    Targeted fish
    Shark (Hammerhead)
    Hammerhead Shark
    Shark (Blacktip)
    Blacktip Shark
    Shark (Tiger)
    Tiger Shark
    Shark (Nurse)
    Nurse Shark
    Shark (Bull)
    Bull Shark
    Shark (Lemon)
    Lemon Shark
  • Private trip
    Half Day Trip (PM)
    FREE Cancellation 3 days notice
    4 Hour Trip, starts at 1:00 PM
    Price for up to 6 persons
    US $750
    There will be $150 fuel surcharge do at the boat. We would be delighted to arrange a 4-hours fishing trip for. you. Our captain is knowledgeable and experienced and will be able to advise you on the best target fish depending on weather conditions. We will always try to fulfill. your request, and ensure that you have a productive and enjoyable day. Please let us know if you have any questions or special request and we will do our best to accommodate you. Thank you again for choosing us!
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Amberjack
    Amberjack
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Grouper (Black)
    Black Grouper
    Tuna (Blackfin)
    Blackfin Tuna
    Bonito
    Bonito
    Shark (Bull)
    Bull Shark
    Cero Mackerel
    Cero Mackerel
  • Private trip
    3/4 Day Trip (AM)
    In demand! Last booked: 6 days ago
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 8:00 AM
    Price for up to 6 persons
    US $1,050
    There will be a $150 furl durcharge due at the dock the morning of your ttip.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Amberjack
    Amberjack
    Cobia
    Cobia
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Grouper (Black)
    Black Grouper
    Tuna (Blackfin)
    Blackfin Tuna
    Bonito
    Bonito
    Shark (Bull)
    Bull Shark
    Cero Mackerel
    Cero Mackerel
  • Private trip
    3/4 Day Trip (PM)
    FREE Cancellation 3 days notice
    6 Hour Trip, starts at 12:00 PM
    Price for up to 6 persons
    US $1,050
    It will be $150 fuel surcharge do on the day of your trip.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Amberjack
    Amberjack
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Grouper (Black)
    Black Grouper
    Snapper (Mutton)
    Mutton Snapper
    Snapper (Yellowtail)
    Yellowtail Snapper
    Tuna (Blackfin)
    Blackfin Tuna
    Bonito
    Bonito
    Shark (Bull)
    Bull Shark
    Cero Mackerel
    Cero Mackerel
  • Private trip
    Full Day Trip
    FREE Cancellation 3 days notice
    8 Hour Trip, starts at 8:00 AM
    Price for up to 6 persons
    US $1,350
    There will be $150 fuel surcharge due at the boat the morning of your trip.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Wreck Fishing
    Fishing techniques
    Deep Sea Fishing
    Bottom Fishing
    Light Tackle
    Jigging
    Kite Fishing
    Heavy Tackle
    Trolling
    Spinning
    Targeted fish
    Barracuda (Great)
    Great Barracuda
    Amberjack
    Amberjack
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Marlin (Blue)
    Blue Marlin
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Grouper (Black)
    Black Grouper
    Shark (Blacktip)
    Blacktip Shark
    Tuna (Blackfin)
    Blackfin Tuna
    Bonito
    Bonito
    Shark (Bull)
    Bull Shark
    Cero Mackerel
    Cero Mackerel
There are 6 people looking at this charter.

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 22 reviews
Boat
Excellent
4.7 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.7 / 5
Photos & videos by reviewers (28)
Wonderful successful trip!
Wonderful successful trip!
Wonderful successful trip!
+25
Angler rating
19
2
1
0
0
Anglers claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
95%
Appropriate for children
100%
Satisfied with the boat
100%
Caught fish
100%
Sort by:
Featured  
Showing:
5 of 22 reviews
Daniel Y.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Father and son trip

VERIFIED   Half Day Trip (AM) 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...
Daniel Y. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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  Cowboy Cowgirl Sportfishing Charters Charter Operator replied

Mark J.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Capt Sam

VERIFIED   Full Day Trip on August 8, 2024
Went out with Sam and Steve 2 days in a row, and both days they had us in the fish! From what we heard over the radio, other...
Mark J. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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Mark J. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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Brian M.
Excellent
4.7 / 5
Experience:
Very good
4.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Wonderful successful trip!

VERIFIED   NEW  Half Day Trip (AM) on November 22, 2024
The crew was very knowledgeable. Tried several tactics to find fish. Very polite and accommodating. The owners were very communicative...
Brian M. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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Brian M. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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Kurt H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Big nurse shark

VERIFIED   Inshore Shark Fishing Trip (AM) on July 10, 2024
Captains Paul and John did a great job putting us on fish My grandson and son caught a barracuda and a seven foot nurse shark...
Kurt H. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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Kurt H. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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Joel H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Very determined crew

VERIFIED   3/4 Day Trip (AM) on March 21, 2024
The captain and first mate were very determined to put us on fish. They had us on a bite immediately upon getting to the spot....
Joel H. recommends Cowboy Cowgirl Sportfishing – Cowgirl II
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1 person finds this review helpful
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  Cowboy Cowgirl Sportfishing Charters Charter Operator replied

FAQs about Cowboy Cowgirl Sportfishing – Cowgirl II

Cowboy Cowgirl Sportfishing – Cowgirl II offers the following trips to customers:
  • US $600 per group - Inshore Shark Fishing Trip (AM) (4 hours)
  • US $600 per group - Inshore Shark Fishing Trip (PM) (4 hours)
  • US $750 per group - Deep Water Shark Fishing Trip (AM) (4 hours)
  • US $750 per group - Half Day Trip (AM) (4 hours)
  • US $750 per group - Half Day – Deep Water Shark (PM) (4 hours)
  • US $750 per group - Half Day Trip (PM) (4 hours)
  • US $1,050 per group - 3/4 Day Trip (AM) (6 hours)
  • US $1,050 per group - 3/4 Day Trip (PM) (6 hours)
  • US $1,350 per group - Full Day Trip (8 hours)

When you book a trip with Cowboy Cowgirl Sportfishing – Cowgirl II, you can expect the following amenities onboard:
  • Toilet We have an enclosed bathroom on board for your privacy and comfort
  • GPS
  • Fishfinder
  • Bed
  • Flybridge
  • Live Bait Well
  • Ice Box

Trips booked with Cowboy Cowgirl Sportfishing – Cowgirl II include:
  • Rods, reels & tackle
  • Live Bait (We provide live bait when it’s available and beneficial for the catch. If gathering bait takes extra time, we’re happy to extend the trip as needed to ensure a full fishing experience)
  • Lures
  • Catch cleaning & filleting (We don’t charge extra for cleaning or filleting your catch—it’s part of the mate’s job. A customary 20% tip is appreciated to recognize their hard work)
  • First Mate (A skilled first mate is always on board to assist with all aspects of your trip. A 20% tip is customary and appreciated to recognize the crew's hard work and dedication)
  • Fishing License (All necessary fishing licenses are included in the price, so you’re fully covered and ready to fish)

Cowboy Cowgirl Sportfishing – Cowgirl II offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Reef Fishing
  • Wreck Fishing

Cowboy Cowgirl Sportfishing – Cowgirl II offers the following fishing techniques:
  • Light Tackle
  • Bottom Fishing
  • Trolling
  • Spinning
  • Kite Fishing
  • Bowfishing
  • Deep Sea Fishing

Top targeted fish species with Cowboy Cowgirl Sportfishing – Cowgirl II include:
  • Amberjack
  • Barracuda (Great)
  • Bonito
  • Cero Mackerel
  • Cobia
  • Dolphin (Mahi Mahi)
  • Grouper (Black)
  • Grouper (Gag)
  • Sailfish
  • Shark (Bull)
  • Tuna (Blackfin)
  • Wahoo

Your operator

Cowboy Cowgirl Sportfishing Charters
Stock Island, Florida, United States
5 Fishing Reports
ID & license verified
627 Customer reviews
Response time within an hour
Member since June 2014
Legendary Sportfishing in Key West – 60 Years Strong, Three Generations Deep! Step aboard one of our 6 premier fishing vessels, where 60 years of fishing excellence meets thrilling adventures in the world-renowned waters of Key West, FL. A family tradition spanning three generations, our fleet of six exceptional boats offers something for everyone – from seasoned anglers to families looking for an unforgettable day on the water. With a legacy of winning tournaments and creating lifelong memories, we specialize in offshore action for some of the most exciting species Key West has to offer. From bottom fishing to Offshore– our trips are all about chasing the big bites that make your heart race, whether it’s the dazzling Mahi Mahi, powerful Tuna, sleek Wahoo, or acrobatic Sailfish. A Fleet Built for Adventure Whether you’re looking for a luxurious offshore fishing experience or a shared group charter, our fleet is ready to deliver. Each boat is fully equipped with tournament-grade gear, spacious seating, and all the amenities you need for comfort and excitement on the water. From our iconic fleet, our vessels are helmed by captains with experience and unmatched knowledge of these legendary fishing grounds. Unmatched Expertise, Endless Thrills Fishing with our fleet isn’t just a trip – it’s a chance to learn from a team with generations of angling expertise. Our captains and crew know the waters of Key West like the back of their hand, and they’re here to ensure you have the trip of a lifetime. Whether it’s mastering trolling techniques, spotting fish, or simply enjoying the stunning views, we’ll make sure you leave with incredible memories. What’s Included: Top-tier equipment: Rods, reels, bait, tackle – we’ve got it covered. Family-friendly service: Trips suitable for anglers of all ages and experience levels. Catch care: Your captain will clean and fillet your catch for you. Comfort: Modern boats with shaded seating, clean restrooms, and plenty of space. Come fish with a team that’s been making dreams come true for six decades. Cowboy Cowgirl Sportfishing Charters is more than a fishing trip – it’s a slice of Key West history, filled with adventure, expertise, and passion. Book your trip today and discover why we’re one of the most celebrated names in Key West fishing!

The fish you can target

Amberjack Amberjack
Barracuda (Great) Great Barracuda
Bonito Bonito
Cero Mackerel Cero Mackerel

What the boat is 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

Which types of fishing are offered

Inshore Fishing
Nearshore Fishing
Reef Fishing
Wreck Fishing

Which fishing techniques you can try

Light Tackle
Bottom Fishing
Trolling
Spinning
Kite Fishing
Bowfishing
Deep Sea Fishing

Which amenities are available onboard

Toilet
We have an enclosed bathroom on board for your privacy and comfort
GPS
Fishfinder
Bed
Flybridge
Live Bait Well

What’s included in the trip price

Rods, reels & tackle
Live Bait
We provide live bait when it’s available and beneficial for the catch. If gathering bait takes extra time, we’re happy to extend the trip as needed to ensure a full fishing experience
Lures
Catch cleaning & filleting
We don’t charge extra for cleaning or filleting your catch—it’s part of the mate’s job. A customary 20% tip is appreciated to recognize their hard work
First Mate
A skilled first mate is always on board to assist with all aspects of your trip. A 20% tip is customary and appreciated to recognize the crew's hard work and dedication
Fishing License
All necessary fishing licenses are included in the price, so you’re fully covered and ready to fish

How cancellations work

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
Kids of all ages are welcome! There’s no age limit, and our friendly crew ensures a fun and safe experience for young anglers
You Keep Catch
Catch and Release Allowed

How you can pay

Book with 10% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Visa
Mastercard
American Express
PayPal
When paying the remaining balance with a credit card, an additional 3.5% charge will apply.

What’s biting in Stock Island right now

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