Cowboy Cowgirl Sportfishing Charters
Cowboy Cowgirl Sportfishing Charters
Cowboy Cowgirl Sportfishing Charters
5
Boat Tours • Water Sports • Fishing Charters & Tours
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7:00 AM - 11:00 PM
Monday
7:00 AM - 11:00 PM
Tuesday
7:00 AM - 11:00 PM
Wednesday
7:00 AM - 11:00 PM
Thursday
7:00 AM - 11:00 PM
Friday
7:00 AM - 11:00 PM
Saturday
7:00 AM - 11:00 PM
Sunday
7:00 AM - 11:00 PM
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About
For over 55 years, our family-owned charter boat business has been providing the best fishing experiences in Key West, Fl. We are a third-generation business, providing customers with a unique blend of knowledge, experience, and passion for fishing. Our crew is professionally trained and certified, offering a variety of fishing trips, from deep-sea to reef fishing and many more. We offer both Private and Shared charters to accommodate all price ranges. We believe in providing our customers with the utmost care and attention, ensuring they have the best possible experience while out on the water. We strive to create an unforgettable experience that customers will want to come back. Thank you for choosing us for your fishing experience.
Key West, Florida
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Awards
Travelers' Choice
2022
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Cowboy Cowgirl Sportfishing Charters
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(58 reviews)

(22 reviews)

(35 reviews)
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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
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5.0
320 reviews
Excellent
291
Very good
8
Average
4
Poor
5
Terrible
12
cjc00per
Branson, MO10 contributions
Jan 2021
Ooohh, Barracuda !!
Our fishing afternoon on the Cowgirl was a great experience. The air conditioned cabin was very nice for some of our party when the seas got a little rough.
We had a sail fish toying with our bait but could not get him hooked. Everyone was able to catch a fish and we highly recommend Capt John and Mate Taylor for an exciting day and a beautiful view of the sunset on our return to port...
Our fishing afternoon on the Cowgirl was a great experience. The air conditioned cabin was very nice for some of our party when the seas got a little rough.
We had a sail fish toying with our bait but could not get him hooked. Everyone was able to catch a fish and we highly recommend Capt John and Mate Taylor for an exciting day and a beautiful view of the sunset on our return to port...
Written January 10, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Lars P
2 contributions
May 2022 • Friends
Had the privilege to spend 4 hours on the water with the owner, Mark, and one of his top crew mates, Johnny. Both locals of Key West that know the ins and outs and are willing to guide & share. Totally a 5-star experience from start to finish. The team curates each session based on current conditions by the hour, ability of the client & overall goals of the client. Johnny was polite & methodical in his approach, even when coaching us up with a 20lb Black Grouper on the line for 5 minutes! If you’re looking to go have a good time and swing for the fences, I highly recommend this team. The best part was slicing up our fish at the dock and hanging out with the rest of the crew to hear stories from the day. They recommended we take our fresh catch to Kayas in downtown. I called the main line and the owner/chef picked up right away, got us a table within an hour and it was an unreal 3-course meal with the same fish. Cheers.
Written May 3, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
CT
2 contributions
Mar 2021
Great Charter! Went on a Full day with Capt. Phil and Russia and they did not disappoint!
When I got to the dock I told them I always wanted to catch a Sailfish and they worked very hard to make that dream a reality. We pulled in a beautiful 8 1/2 footer and they even assisted with helping order the mount. Caught a few other fish as well and a nice Mahi that we took to Dante’s for dinner that night....delicious!
Don’t hesitate to book with Cowboy and request Capt Phil and Russia if possible!
Lastly, the whole booking process was seamless and I highly recommend just calling Cowboy Charters directly instead of going through the normal third party booking sites that charge the company’s fees. They always answer the phone and are super helpful.
When I got to the dock I told them I always wanted to catch a Sailfish and they worked very hard to make that dream a reality. We pulled in a beautiful 8 1/2 footer and they even assisted with helping order the mount. Caught a few other fish as well and a nice Mahi that we took to Dante’s for dinner that night....delicious!
Don’t hesitate to book with Cowboy and request Capt Phil and Russia if possible!
Lastly, the whole booking process was seamless and I highly recommend just calling Cowboy Charters directly instead of going through the normal third party booking sites that charge the company’s fees. They always answer the phone and are super helpful.
Written March 16, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Kristi R
6 contributions
Jun 2022 • Family
When my husband booked this we told the lady on the phone we were beginners and have never fished and she oversold this company on being great for beginners and how they cater to them, just like most of their ads say. We even asked if there was a first mate and they said, its just the captain but we are very good with beginners and take them out all the time. We let the captain know we were beginners and we never fished and how we basically book this for our 12 year old son. Well.. the captain sucked, he never even showed my son one thing, nor was he kid friendly. The only one who fished on the boat of 5 was the guy who knew how to fish prior. The one time my son did get to reel something in, he asked "how do I do it?" and captain responded "reel it in" and thankfully the other guy (who paid to be on the charter) helped him. We caught 2 TWO SMALL fish (and lots of weeds) in 4 hours, he threw them back in so fast you couldn't even see them!! The time my son got to reel it in it i was excited thinking he had a fish.. NO, cuz the lines were all tangled together! 🙄 There was only 2 rods that could be reeled in by ppl on the boat cuz thats how small the back area was that you could actual fish on. So why put 5 ppl on a boat together, if only 2 can fish at a time?!? We walked away disappointed, not only in the catch of 2 fish, but with the captain! This guy wasn't kid friendly, he looked overly tired and didn't even trying to engage in any kind of conversation or guidance to help my son. I'm guessing he tried to find fish cuz he moved 3-4x, but to only catch 2 in the ocean.. geez! Such ashame to see other ppl at the docks with tons of fish, maybe this captain should ask them where they go...
When we got back to our hotel, we seen some guy bring in a bag of fish to the cook and my husband asked which charter he went on and it was Gulfstream, this guy had several bags of fish and actually gave us a bag because we explained our situation and he felt so bad for our son. It just shows a public/private charter isn't better, especially with this company.
When we got back to our hotel, we seen some guy bring in a bag of fish to the cook and my husband asked which charter he went on and it was Gulfstream, this guy had several bags of fish and actually gave us a bag because we explained our situation and he felt so bad for our son. It just shows a public/private charter isn't better, especially with this company.
Written June 25, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Rob N
Adams, TN2 contributions
Jul 2022 • Family
We booked a 3/4 day offshore trip (6hrs) with the crew of the cowgirl and had a blast! Michelle, Captain Sharky and John all made us feel like family. Captain Sharky did a great job finding the fish. John was great with the kids and enthusiastic. He really made the trip fun for them. They even let my 5 year old sleep on a bunk bed.
During our trip we went about 9 miles (I believe), trolling for Mahi, Tuna, Wahoo, Cuda and whatever else wanted to bite. We ended up catching a nice 20-25lb Wahoo, a couple nice Cudas and a Bonita. When we got back to the dock, Michelle was there to greet us and take our picture.
It was a really fun trip and we HIGHLY recommend booking any of the charters with Cowboy Cowgirl Charters.
During our trip we went about 9 miles (I believe), trolling for Mahi, Tuna, Wahoo, Cuda and whatever else wanted to bite. We ended up catching a nice 20-25lb Wahoo, a couple nice Cudas and a Bonita. When we got back to the dock, Michelle was there to greet us and take our picture.
It was a really fun trip and we HIGHLY recommend booking any of the charters with Cowboy Cowgirl Charters.
Written July 30, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Carly M
9 contributions
Dec 2020 • Family
Awesome crew! Great time and even got to go out a little early because they said the fish were biting like crazy! Taylor and Sharky were super nice and very helpful. Caught some great fish and more importantly, enjoyed the early morning out on the ocean. Taylor went above and beyond the entire time, pointed out sea turtles, other fish, and was in a great mood. Sharky was all all around great captain with tons of knowledge. Both guys were positive and just as excited for us to catch fish. Would recommend 100%.
Written December 15, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Matthew B
Atlanta, GA5 contributions
Feb 2022 • Couples
My wife and I had a great time on the Cowgirl boat with Blue as our captain and Nick as our mate! We went out for a half day afternoon charter and hooked a couple of barracuda, a massive king mackerel and a small Spanish mackerel. Nick and Blue were super friendly and knowledgeable. They made a great restaurant recommendation at Kaya to take our catch for them cook up our mackerel in several different preparations.
We would definitely book with this charter again, and would recommend for anybody looking for a great fishing experience!!
We would definitely book with this charter again, and would recommend for anybody looking for a great fishing experience!!
Written February 22, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Don L
3 contributions
Jul 2022
We had booked a fishing trip with Corsair II, and after our booking was cancelled upon us last minute (while sitting on the boat with the captain), several fishermen around the marina recommended us to call cowboy and see if we could get in. The owners had given the captains and mates the day off but captain Nell came in on his off day for us. The trip with cowboy cowgirl provided by captain Nell left me and my family glad that our first booking was cancelled. We caught several massive yellowtail snapper including a 22 inch rod bender. We couldn't recommend them more. Not only for the fishing, but also the great humor and experience of the captain and his first mate. While Sanctuary, their boat, may not be the fastest an indoor air conditioned cabin and large hull make the trip to and from the fishing spots much more comfortable and easier if traveling with someone who wouldn't appreciate the waves being felt on a smaller boat. If the captains give you the option to extend, as they did us, take them up on it. Once you start catching you won't want to leave.
Written July 12, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
andicoop
Fort Worth, TX2 contributions
Oct 2021 • Family
We booked a charter for 1:00, but I think the 8am would have been better because we only caught one fish. We got on the boat Sanctuary and the AC in the cabin was broken and the toilet was backed up. Not a pleasant experience. Our captain Jesse was a super nice guy tho and gave us almost an extra hour since the fish weren’t biting.
Written October 12, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Dickson M
1 contribution
Jan 2022 • Couples
We had an amazing trip with Captain "Sharky" Mark and John. Would couldn't have asked for a better crew. They were great with those that had experience and even better with those with little to no experience. And what else can I say besides after pulling in a couple fish, Captain put us on a Sailfish and him and John coached us though our first landed Sailfish! Absolutely an epic trip.
Written January 26, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
No questions have been asked about this experience