High Stakes Charters

High Stakes Charters

High Stakes Charters
5
About
High Stakes Charters offers a 53’ Striker Sport Fisherman for deep sea fishing in Key West, Florida. You get so much more bang for your buck if you charter us. For starters you get a spacious 53' A/C sportfishing vessel. We can accommodate up to 6 guests. Reclining leather couches, two bathrooms, galley, fighting chair, tournament style tackle and crew with 35 combined years experience. In fall of 2019, High Stakes underwent a major engine room upgrade and restoration. We now have brand new 650 HP Caterpillar engines. This upgrade allows our customers more time fishing and less time traveling. It takes approximately 17 minutes and is a straight shot to the fishing grounds from Oceans Edge Resort and Marina, on the south side of the island. High Stakes is the FASTEST and BIGGEST boat for charter in Key West. Enjoying the magnificant waters off the Keys while catching fish is the perfect vacation! Come join us for your next Key West fishing trip!
Key West, United States
Meets animal welfare guidelines

Awards
Travellers' Choice
2024

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Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

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5.0
5.0 of 5 bubbles302 reviews
Excellent
298
Very good
2
Average
0
Poor
2
Terrible
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Cynthia V
10 contributions
5.0 of 5 bubbles
Mar 2023 • Family
We booked a 10 hour trip for 6 people (2 grandparents, 2 adults and 2 kids, ages 10 and 14). Communication regarding booking and just prior to the trip was excellent. Weather and wind conditions weren’t great the morning of the trip, so Captain Jason adjusted the time and we left a bit later and just stayed out later. The trip was excellent. Captain Jason and his first mate were highly knowledgeable and made the trip enjoyable for all. The boat is very nice with comfortable seating inside and out. We would highly recommend High Stakes and can’t wait to book our next trip.
Written 21 May 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Daniel H
1 contribution
5.0 of 5 bubbles
Oct 2023 • Family
We had a blast! I’ve grown up here in Florida fishing and have to say Captain Jason and Matt are highly skilled and worked hard to put us on the Mahi and I would highly recommend booking a trip with them if you want a great fishing experience. See yall in the Spring to get on some Sailfish!

Thanks again, and our fresh mahi we had hogfish grille cook up like you recommended was on point.
Written 21 October 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Kristine R
1 contribution
5.0 of 5 bubbles
Nov 2023 • Family
We called last minute and they were able to take us out the next day! Captain Jason and First Mate Matt were both fabulous! We caught some beautiful black fin tuna throughout the day and ended our day catching 4 large sailfish! What an amazing day!! They came highly recommended to us and we now highly recommend them to others. Clean boat, great equipment, and fabulous people. You will not regret a day out on the waters with them!
Written 2 November 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Shayne Rice
3 contributions
5.0 of 5 bubbles
Apr 2022 • Friends
Capt. Jason and first mate Matt were phenomenal. It was a tough day for fishing with no wind and current not in our favor for this time of year but they put us on a mature sailfish about four hours into the trip and Matt made sure he did everything in his power to get the hook set for us. Captain maneuvered the boat the whole time the sail fish was on the line to make it as easy as possible. I absolutely cannot speak highly enough of this crew to make this day more enjoyable or successful. Can’t wait to book again.
Written 16 April 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Outstanding!! Thank you for your kind words! We are looking forward to fishing with you again!
Written 16 October 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Mike K
7 contributions
5.0 of 5 bubbles
Apr 2022 • Friends
I can’t say enough about Capt. Jason and his assistant Matt and our trip on the High Stakes charter boat. Without hesitation Jason was flexible with our party after travel delays made us arrive a day late. Once the trip started Matt was on point setting up the rods for some sailfish. Luck was not on our side for the sailfish but it was not from lack of trying. A little over 2/3 of the way into the trip we switched up and started for tuna, and that’s when the action started. Lines started running and we were all pulling in tuna. Matt was non stop getting fish on the boat, rebaiting the hook and getting them back out in the water. At one point all five lines had tuna on them. It was an amazing trip. You will hear Jason say that no one on his boat wants to catch fish more then him. He means it. Both him and Matt worked non stop to get us what we wanted. I highly recommend Jason and going out on High Stakes. They are great people to work with.
Written 6 April 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Outstanding!! Thank you for your kind words! We are looking forward to fishing with you again!
Written 16 October 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

AEB407
Orlando, FL10 contributions
5.0 of 5 bubbles
Jun 2022 • Solo
Had a fantastic two days of fishing with Captain Jason and his crew. Great boat, knowledgeable team, honest approach. Felt right at home from the time I stepped on the boat, and it was clear this is a top notch charter.

There are so many options around Key West, but you need to book with a competent and experienced crew to maximize your trip, and High Stakes is exactly that.

I have been on more than a dozen charters out of Key West over the years and I wouldn’t put anyone above High Stakes. This is the type of boat and operation you should look for. Nothing is guaranteed, but they will put forth their best effort to allow you to be successful.

When TSA complements you on how much fish you are bringing through security, it’s a good sign your captain knows his stuff. Highly recommend!
Written 10 June 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Outstanding!! Thank you for your kind words! We are looking forward to fishing with you again!
Written 16 October 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Russell W
1 contribution
5.0 of 5 bubbles
Jun 2021
Captain Jason and First Mate Matt on the High Stakes in the Oceans Edge Resort Marina. They were friendly and we were on a first name basis in 5 minutes. Best crew on the island! Great service, clean updated 53’ boat, AC in salon (cold even with the door open all day), all equipment up to date and in immaculate condition, the trip was planned around his availability. We took the 10 hour extended trip. Although the weather was terrible for fishing (light changeable wind, broken up sargasso seaweed mats, etc.) Captain Jason still put us in the fish. Matt did awesome work keeping the lures and fresh bait clear of seaweed which meant he was working reel to reel on about a 1 minute interval and still had energy to explain the setup and educate us on the sport. When not in the fighting belt I was in the flying bridge watching the action. We put enough fish in the cooler to feed 7 adults and 6 hangry teenagers with a third of the catch left on the table. Three days later I'm still full! Jason and Matt were the heroes of the day.
Written 16 June 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Doug P
2 contributions
5.0 of 5 bubbles
Jul 2023 • Friends
Captain Jason took three friends and I on an offshore marlin trip to celebrate a bachelor party, and I had the most fun I have ever had.

Captain Jason was welcoming of our touristy excitement, and he was upfront and honest with us about difficult fishing conditions. Nonetheless, we hooked into a ~300 pound marlin, and Captain Jason's excitement and professionalism helped us land and safely release the fish of a lifetime. The memories made on this trip will stick with me forever.
Written 9 July 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Paul H
5 contributions
5.0 of 5 bubbles
Dec 2021
I am a Florida native and ex boat owner life long fisherman. I have said it before I will say it again. When I go to the Keys to go fishing the ONLY boat I will charter is High Stakes. If your serious about hunting fish this is the right boat. if your happy catching or not catching, any boat will do you fine. These guys HUNT, they work non stop hunting for fish. All the boats have rods, reels and bait and most try hard, but these guys go harder then any boat I have been on in the keys. even technology wise, the wear high end headsets to communicate between captain and mate(s), you will not see that on other charter boats. It is also probably the fastest "charter" boat you will find in Key West as well which means less time traveling to and from more time hunting for fish, it makes a huge difference, especially when the fish are way out. It should also be said the boat is in great shape and looks great to, some of these charter boats I would not even think of putting my family on just by looking at them. if you do not try hard to maintain your boat how would I know you would try hard to find me fish?
I have chartered High Stakes 3 times this year, 2 of those trips nobody was catching anything or just tiny schoolies but I maxed out my limit on both and very nice sized, what does that tell you
Written 22 December 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Dan W
8 contributions
5.0 of 5 bubbles
Oct 2023 • Couples
Had a GREAT trip, Jason & Mat both are exceptional and go the extra mile to provide their customers with the best experience possible. They come prepared to make it happen, baits are prepared and in excellent condition. Second time to fish with High Stakes and without any doubt, we will use them again.
Written 6 October 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you for your kind words! Truly looking forward to fishing with you again!
Written 10 October 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

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HIGH STAKES CHARTERS (Key West) - All You Need to Know BEFORE You Go

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