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Cowboy Charters – Blue Cowboy 

4.7
(8 reviews)
 6000 Peninsular Avenue, Stock Island, FL 33040, United States–
+19
+16

Cowboy Charters – Blue Cowboy 

Stock Island, FL, United States
–
34 ft
6
4.7
(8 reviews)
Trips & prices
Targeted species
Boat info
What's biting
What's included
Contact captain
Trips & prices
What's included
Targeted species
Boat info
Reviews
Contact captain

There's no place like Key West to fulfill your fishing dreams and if you're looking for a company to lead the charge, Cowboy Charters is at your service! Captain Daniel Hawkins and his skilled crew know the ways of the fish and are happy to share the knowledge with their customers.

It will all start on a comfortable 34' Contender with plenty of space to sit up to 6 adventurous anglers and twin 300 HP Yamaha engines. The vessel is rigged with the top-notch navigational equipment to keep you on your prey and a live bait well. If you're going on a longer expedition, there's a private porta potty on board, so you can fish without a worry in the world.

But the top-of-the-line boat is only one of many perks Cowboy Charters has to offer. The professional crew makes it their mission to put you on the bite. Chase Billfish superstars like White Marlin and Sailfish, or land sizeable Mahi Mahi, Mutton Snapper, and Amberjack. If your thrill is chasing apex predators, targeting Sharks is another specialty of Capt. Daniel. The waters around Key West are as plentiful as they are varied.

Feel free to come fishing with your kids, all ages are welcome aboard. The crew will have safety jackets for everyone. You'll find all the fishing gear you need on the boat, including reliable Venspaal and Penn spinning rods. At the end of the day, you will get your catch cleaned and filleted for your convenience.

Everything will be provided for your next fishing escapade, just remember to bring your favorite food and drinks for the trip, and leave everything else in the capable hands of Cowboy Charters! New fishing horizons await!

There's no place like Key West to fulfill your fishing dreams and if you're looking for a company to lead the charge, Cowboy Charters is at your service! Captain Daniel Hawkins and his skilled crew know the ways of the fish and are happy to share the knowledge with their customers.

It will all start on a comfortable 34' Contender with plenty of space to sit up to 6 adventurous anglers and twin 300 HP Yamaha engines. The vessel is rigged with the top-notch navigational equipment to keep you on your prey and a live bait well. If you're going on a longer expedition, there's a private porta potty on board, so you can fish without a worry in the world.

But the top-of-the-line boat is only one of many perks Cowboy Charters has to offer. The professional crew makes it their mission to put you on the bite. Chase Billfish superstars like White Marlin and Sailfish, or land sizeable Mahi Mahi, Mutton Snapper, and Amberjack. If your thrill is chasing apex predators, targeting Sharks is another specialty of Capt. Daniel. The waters around Key West are as plentiful as they are varied.

Feel free to come fishing with your kids, all ages are welcome aboard. The crew will have safety jackets for everyone. You'll find all the fishing gear you need on the boat, including reliable Venspaal and Penn spinning rods. At the end of the day, you will get your catch cleaned and filleted for your convenience.

Everything will be provided for your next fishing escapade, just remember to bring your favorite food and drinks for the trip, and leave everything else in the capable hands of Cowboy Charters! New fishing horizons await!

Cowboy Cowgirl Sportfishing Charters
Charter Operator
Cowboy Cowgirl Sportfishing Charters
61 years of experience
responds within an hour
What this charter offers
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Child friendly
What this charter offers
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Child friendly

Select date to see availability

Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
Group Size
2 adults • 0 children
Change
Half Day Trip (AM)
FREE Cancellation 3 days notice
4 hour trip starts at 8:00 AM
US $1,250
Entire boat: up to 6 people
Half Day Trip (PM)
FREE Cancellation 3 days notice
4 hour trip starts at 1:00 PM
US $1,250
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 3 days notice
6 hour trip starts at 8:00 AM
US $1,550
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 3 days notice
8 hour trip starts at 8:00 AM
US $1,750
Entire boat: up to 6 people

Customer reviews

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Rating

4.7
8 reviews
5.0
Boat & equipment
4.6
Captain & crew
4.6
Fishing Experience

Anglers' gallery (10)

Reviews (8)

  • Logan Heaps
    Logan Heaps
    us
    South Carolina, US
    Member since 2021
    5.0
    Verified

    3/4 trip with Captain Phil

    3/4 Day Trip on May 15, 2021 • 4 adults

    Phil was an awesome captain with cowboy charters. Phil went above and beyond, he worked his butt off making sure we had as many lines out as possible and fresh bait. We caught about 12-15 dolphin. We did this as a last minute thing and it couldn't have been better decision! I highly recommend getting phil as your offshore charter guide

  • John Preiss
    John Preiss
    us
    New Jersey, US
    Member since 2022
    5.0
    Verified

    January fishing trip

    3/4 Day Trip on January 8, 2022 • 4 adults
  • Anthony Russo
    Anthony Russo
    us
    Florida, US
    Member since 2021
    5.0
    Verified

    3/4 day wirh Capt. Jake

    3/4 Day Trip on December 22, 2021 • 2 adults

    Had some sporty conditions, but Capt. Jake made it as comfortable as possible. Perfect boat outfitted for fishing in Key West and Jake put us on the meat. I am a current Captain myself of a yacht and Jake took great care of the guests I brought aboard the charter. First class guy and he knows the area well. Highly recommend!

  • Karen Tingler
    Karen Tingler
    us
    North Carolina, US
    Member since 2020
    5.0
    Verified

    October fishing trip

    Half Day Trip (AM) on October 31, 2020 • 4 adults
  • James Schulenberg
    James Schulenberg
    us
    Texas, US
    Member since 2020
    5.0
    Verified

    Fishing with Michelle

    3/4 Day Trip on March 19, 2020 • 3 adults • 1 child
  • William Bywaters
    William Bywaters
    Repeat angler
    us
    Texas, US
    Member since 2019
    3 trips
    5.0
    Verified

    Fishing with Michelle

    3/4 Day Trip on April 20, 2019 • 2 adults
  • Frank Slawitschka
    Frank Slawitschka
    us
    Florida, US
    Member since 2021
    3.0
    Verified

    3/4 day on a nice Contender center console.

    3/4 Day Trip on February 18, 2021 • 2 adults

    Was rough and it appeared the captain either was overwhelmed or wasn't sure how to put us on any fish. Other boats from the fleet were radioing the fish they were catching in the same area but we didn't catch any fish. For $950 we were very disappointed to say the least.

FAQs about Cowboy Charters – Blue Cowboy

Cowboy Charters – Blue Cowboy offers the following trips to customers:
  • US $1,250 per group - Half Day Trip (AM) (4 hours)
  • US $1,250 per group - Half Day Trip (PM) (4 hours)
  • US $1,550 per group - 3/4 Day Trip (6 hours)
  • US $1,750 per group - Full Day Trip (8 hours)
When you book a trip with Cowboy Charters – Blue Cowboy, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Live bait well
  • Ice box
Trips booked with Cowboy Charters – Blue Cowboy include:
  • Rods, reels & tackle
  • Live bait
  • Lures
  • Catch cleaning & filleting
  • Fishing license
Cowboy Charters – Blue Cowboy offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
  • Offshore fishing
  • Reef fishing
  • Wreck fishing
  • Backcountry fishing
Cowboy Charters – Blue Cowboy offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Bottom fishing
  • Trolling
  • Spinning
  • Jigging
  • Drift fishing
  • Kite fishing
  • Deep sea fishing
Top targeted fish species with Cowboy Charters – Blue Cowboy include:
  • Amberjack
  • Barracuda (Great)
  • Dolphin (Mahi Mahi)
  • Marlin (Blue)
  • Marlin (White)
  • Sailfish
  • Shark (Bull)
  • Shark (Hammerhead)
  • Shark (Mako)
  • Shark (Tiger)
  • Snapper (Mutton)
  • Tarpon

Your operator

Cowboy Cowgirl Sportfishing Charters
Cowboy Cowgirl Sportfishing Charters
Stock Island, Florida, United States
19 Fishing Reports
737 Customer reviews
Member since June 2014
Legendary Sportfishing in Key West: 60 Years Strong, Three Generations Deep! Step aboard one of our six 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 fishing, 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. Our vessels are helmed by experienced captains with 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 backs of their hands, 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, and tackle are provided. Family-friendly service: Trips are 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!
Our Team
Capt Woody (Sam) W.
Capt Woody (Sam) W.
Captain
Capt Cole B.
Capt Cole B.
Captain
Sharky (Mark) B.
Sharky (Mark) B.
Business partner
Capt Cuzzy (Chris) B.
Capt Cuzzy (Chris) B.
Captain
Cowboy Cowgirl Sportfishing Charters
Cowboy Cowgirl Sportfishing Charters
19
reports
737
reviews
2014
member since
Legendary Sportfishing in Key West: 60 Years Strong, Three Generations Deep! Step aboard one of our six 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 fishing, 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. Our vessels are helmed by experienced captains with 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 backs of their hands, 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, and tackle are provided. Family-friendly service: Trips are 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 crew
Capt Woody (Sam) W.
Capt Woody (Sam) W.
Captain
Capt Cole B.
Capt Cole B.
Captain
Sharky (Mark) B.
Sharky (Mark) B.
Business partner
Capt Cuzzy (Chris) B.
Capt Cuzzy (Chris) B.
Captain

The fish you can target

Amberjack
Amberjack
Great Barracuda
Great Barracuda
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Blue Marlin
Blue Marlin
White Marlin
White Marlin
Sailfish
Sailfish
Bull Shark
Bull Shark
Hammerhead Shark
Hammerhead Shark
Mako Shark
Mako Shark
Tiger Shark
Tiger Shark
Mutton Snapper
Mutton Snapper
Tarpon
Tarpon
Amberjack
Amberjack
Great Barracuda
Great Barracuda
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Blue Marlin
Blue Marlin
White Marlin
White Marlin

Real catches by this captain

  • Three young passengers seated inside a center-console fishing boat at a marina, with the helm and T-top visible.
    Fish 1
    Bonnethead Shark
    John P.
    John P.
  • Solo angler holding a colorful mahi-mahi aboard a center-console boat in open ocean waters.
    Fish 1
    Dolphin (Mahi Mahi)
    Logan H.
    Logan H.
    Phil was an awesome captain with cowboy charters. Phil went above and beyond, he worked his butt off making sure we had as many lines out as possible and fresh bait. We caught about 12-15 dolphin. We did this as a last minute thing and it couldn't have been better decision! I highly recommend getting phil as your offshore charter guide

What is the boat like?

Boat image
Boat category
Center console boats
Capacity
6 persons
Boat length
34 ft
Year built
2018
Boat manufacturer
Contender
Boat type
Center console
Engine model
Yamaha
Powered by
2 x 300HP
Max cruising speed
35 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Drift Fishing
Kite Fishing
Deep Sea Fishing

Which amenities are available onboard

GPS
Fishfinder
Live bait well
Ice box
What's included in the trip price
Rods, reels & tackle
Live bait
Lures
Catch cleaning & filleting
Fishing license

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.
More details

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child friendly
All ages welcome
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
 Checks
 Bank transfer
When paying the remaining balance with a credit card, an additional 3% charge will apply.

What’s biting in Stock Island right now

AmberjackAmberjack
Barracuda (Great)Barracuda (Great)
Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
Marlin (Blue)Marlin (Blue)
SailfishSailfish
Shark (Bull)Shark (Bull)
Snapper (Mutton)Snapper (Mutton)
TarponTarpon

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Current
Cowboy Charters – Blue Cowboy
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34 ft
Group size 1 - 6
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+10
4 hour trip • 6 persons
US $1,250