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2024 Tournament Winners

High Stakes Charters, under the expert leadership of Captain Jason Jonas, has an impressive track record of success in competitive sportfishing. The team secured victory in both the 2024 Sailfish Tournament and the prestigious 2013 Key West Drambuie Marlin Tournament, solidifying their reputation among the sport’s elite. Captain Jason Jonas has consistently demonstrated his skill, with his tournament charters earning over $200,000 in prize money. His relentless pursuit of excellence has also led to numerous top placements in other competitive events, making High Stakes Charters a dominant force in the world of professional fishing.

deep sea charter fishing key west

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Meet The Crew

Join Captain Don and Captain Jason Jonas, a skilled father/son duo, along with experienced first mate Matt Bronson, for an unforgettable day on the water!

High Stakes Crew

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Key West Charter Fishing – Deep Sea Tournament Fishing

High Stakes Charters offers an unparalleled deep-sea fishing experience in the beautiful waters of Key West, Florida. Whether you’re an avid angler or simply looking for an unforgettable day on the water, the pristine fishing grounds just miles from shore provide the ideal setting for your perfect getaway.
With a variety of customizable options, High Stakes Charters caters to your unique vacation needs. Whether it’s a thrilling day of fishing with family and friends, we are dedicated to making your trip truly memorable.
Captain Jason Jonas, a seasoned and licensed professional, has spent years fishing the waters of the Florida Keys. His expertise and passion for fishing are called upon daily to deliver an exceptional experience for every guest.
For an adventure that promises excitement and success, choose High Stakes Charters—the premier destination for deep-sea fishing in Key West. Let us help you make your fishing dreams a reality!

Deep Sea Fishing!!

A fantastic adventure ! Jason& Don made this a trip of a life time. One I’ll never forget. Fishing was great the boat beautiful. !!! This is a must do trip! Thank you Jason & Don again .

Great Time!

Fantastic day of fishing in a bit of choppy water. Would return without hesitating. Jason and Don are the hardest working crew I have ever fished with. And, follow their advice and have the fish cooked for you at Hogfish Bar and Grill! Great fried, blackened and grilled fresh fish! Thanks, guys!

Awesome Deep Sea Fishing Trip!!!

Thank you so much Jason and Don!! Our day started with me feeling very anxious, I had gotten sea sick during my last deep sea fishing trip (with another charter). Captain Jason and Don were so understanding and reassuring.

The Fishing Trip of a Lifetime

High Stakes Charters came highly recommended by friends of ours who discovered them while vacationing in Key West a year ago. So when we planned a family trip to Key West for January 2014, booking a fishing trip with High Stakes Charters was the first thing we did. And let me just say, Captains Jason and Don Jonas did not disappoint. Between the two of them, I’m pretty sure they know everything there is to know about fishing.



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Ready For Deep Sea Fishing?

Our top reviews reflect the unmatched expertise and dedication we bring to every fishing trip. If you’re ready to indulge in an extraordinary deep-sea fishing adventure in Key West, FL, we invite you to experience High Stakes Charters!
From our pristine 53′ Striker Sport fishing vessel to our decades of experience navigating the high seas, we are committed to delivering a fishing experience like no other. Let us take your Key West adventure to the next level with our exceptional service and passion for the sport. Choose High Stakes Charters for a world-class fishing experience you’ll never forget!

Call us to reserve your charter today!

(305) 294-8040

What others say about us

Absolutely the best experience one could have!! Captain Jason & Don were incredible! A killer of a catch; 2 wahoo, 2 blackfin tuna, 2 barracuda, some Bonita and a few Mahi and more. Three of us on three lines at one point, all was fantastic. Had a great meal with the days catch and extra for everyone. Captain Jason & Don, thank you a memory that will last a lifetime and “fish stories” to share forever.

You soon realize there are many charters in Key West. But there is only one boat and crew that provides a great trip, adjusts to the weather and makes sure the entire group is happy and satisfied with the fishing charter. Jason found the yellowtail snapper and we even had an opportunity at a giant hammerhead shark!

my family went out with high stakes charters over Thanksgiving week and had a blast even as beginners. The weather was sporty but Jason and Don found us some Mahi

About 30 miles out I caught a 500lb Blue Marlin. It took 2.5 hrs. to bring him in. It was the hardest fight in my life. Capt. Jason knew just how to maneuver the boat to keep the marlin on the line, and to keep it from going under the boat, or past it. I had the greatest support, and coaching to land this once in a lifetime Marlin. We won 1st place in the tournament. We won over $46,000 in cash prizes.