Cowboy Charters – Blue Cowboy 

4.7
(8 reviews)
 6000 Peninsular Avenue, Stock Island, FL 33040, United States

Cowboy Charters – Blue Cowboy 

Stock Island, FL, United States
34 ft
6
4.7
(8 reviews)

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

Select date to see availability

Trip availability and prices

Trip date:
Group Size:
September 2026
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Group Size
2 adults • 0 children
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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
There are 2 people looking at this charter.

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)

All reviews (8)

Showing 15 of 8 reviews
Anthony Russo
Anthony Russo
us
Naples, FL, US
Member since 2021
5.0
Verified
3/4 day wirh Capt. Jake
3/4 Day Trip on December 22, 20212 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!

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, 20214 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, 20224 adults

Karen Tingler
Karen Tingler
us
North Carolina, US
Member since 2020
5.0
Verified
October fishing trip
Half Day Trip (AM) on October 31, 20204 adults

James Schulenberg
James Schulenberg
us
Texas, US
Member since 2020
5.0
Verified
Fishing with Michelle
3/4 Day Trip on March 19, 20202 adults1 child

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
730 Customer reviews
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!

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
730
reviews
2014
member since
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 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

  • 3/4 trip with Captain Phil
    Logan H.
    Logan H.

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
Snapper (Mutton)Snapper (Mutton)
TarponTarpon

Compare similar fishing charters

Current
Cowboy Charters – Blue Cowboy
Cowboy Charters – Blue Cowboy
4.7
(8)
34 ft
Group size 1 - 6
1 - 6
Fish 1
Fish 2
+10
4 hour trip • 6 persons
US $1,250