United States
Florida (FL)
Florida Keys
Key West
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High Stakes Charters
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High Stakes Charters

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High Stakes Charters
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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, Florida
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High Stakes Charters
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(75 reviews)
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
288 reviews
Excellent
284
Very good
2
Average
0
Poor
2
Terrible
0
Russell W
1 contribution
Once a shrimper, now a land lubber... In love with Sport Fishing for the rest of my life!
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 June 16, 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.
Shayne Rice
1 contribution
Fantastic
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 April 16, 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.
HighStakesCharters
Outstanding!! Thank you for your kind words! We are looking forward to fishing with you again!
Written October 16, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Mike K
2 contributions
Trip with Jason and Matt on High Stakes
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 April 6, 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.
HighStakesCharters
Outstanding!! Thank you for your kind words! We are looking forward to fishing with you again!
Written October 16, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Paul H
5 contributions
Best Fishing Charter in Key West
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 December 22, 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.
ScottM
Dallas, PA2 contributions
Excellent! Can't recommend High Stakes enough!
Mar 2021
My friends and I enjoyed an absolutely fantastic day of fishing with Captain Jason and first mate Matt. It's a terrific boat, excellent equipment and Jason and Matt not only know their stuff, they are fun guys to learn from and hangout with.

We caught 5 Blackfin Tuna, a bunch of Barracuda and hooked into a 9-foot Hammerhead that my friend fought for an hour on 20 lb. test.

Lots of fun and lots of laughs. Can't recommend High Stakes enough!
Written March 11, 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.
Cynthia V
1 contribution
Top Notch Offshore Fishing Charter
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 May 21, 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.
Shawn W.
United States4 contributions
High Stakes Charters - An unforgettable experience.
Oct 2020 • Family
The family and I went out on 10-12-20, morning charter. From start to finish , Captain Jason and his First Mate Matt put on a fantastic show . We were fortunate to extend our trip to 6 hours ( which I strongly recommend ) All of the family including myself were able to reel in some decent Mahi . The boat was super comfortable, clean and accommodating for all of us ( 5 in our party ) . Captain Jason even recommended bringing our catch to a local establishment that would cook our Mahi up family style. We highly recommend taking advantage of High Stakes services for an unforgettable experience on the open water ! We have already recommended High Stakes to others in our area. We are headed back in February and will be booking with them again! Thanks guys and my apologies for the delayed review !😂👍🤙🤙
Written October 19, 2020
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.
AEB407
Orlando, FL11 contributions
Excellent experience on a great charter
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 June 10, 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.
HighStakesCharters
Outstanding!! Thank you for your kind words! We are looking forward to fishing with you again!
Written October 16, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
JMBax
Charleston, SC63 contributions
Fun trip
May 2021
I took my entire family on an offshore charter, including 4 who had never been offshore before. Jason and Matt did an excellent job with our crew. Fishing was a little slow, but they worked really hard to put us on fish. Everyone got to catch fish and experience deep sea fishing. We caught a wahoo and several dolphin/mahi. Jason and Matt were great at finding fish and helping our novice crew land fish and enjoy the day.
Written May 15, 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.
Cayce Whitlock
3 contributions
The BEST fishing charter in all of Key West!!
Dec 2019 • Family
My family and I recently went on a fishing charter with High Stakes and it was an experience of a lifetime. I have been on a few other deep sea fishing charters in the past but the High Stakes is like no other. Captain Jason Jonas and first mate Matt Bronson offer a first class experience. They are both highly professional and will make sure you catch the biggest fish out there!! Whether you are a novice or a seasoned fisherman, there is no one better! We caught more Mahi Mahi than we knew what to do with. After our trip, Matt filleted all of the fish and we took it to a local restaurant and had an absolute feast. We also caught Blackfin Tuna and had fresh tuna sashimi on the boat. Not to mention, the High Stakes is absolutely beautiful. It is air conditioned, has bathrooms and has two recliner couches inside to where you can relax. The comfort was unbelievable. My family and I had an absolute blast and will definitely be fishing with the High Stakes again SOON. Thank you Captain Jason Jonas for making all of our fishing dreams come true!!
Written January 19, 2020
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.
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