• Key West deep sea fishing High Stakes
  • key west deep sea fishing
  • Key West deep sea fishing High Stakes
  • Key West deep sea fishing High Stakes
  • Key West deep sea fishing High Stakes
  • Key west deep sea fishing
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Key West deep sea fishing High Stakes
Key West deep sea fishing High Stakes
key west deep sea fishing
key west deep sea fishing
Key West deep sea fishing High Stakes
Key West deep sea fishing High Stakes
Key West deep sea fishing High Stakes
Key West deep sea fishing High Stakes
Key West deep sea fishing High Stakes
Key West deep sea fishing High Stakes
Key west deep sea fishing
Key west deep sea fishing

The Vessel

High Stakes Charters invites you to experience fishing at its finest aboard our 53’ Striker Sport Fisherman, the largest and fastest charter vessel in Key West. After a major engine room overhaul in the fall of 2019, we are proud to feature brand new 650 HP Caterpillar engines. This significant upgrade means less time traveling and more time fishing, giving you maximum enjoyment on the water. Located at Oceans Edge Resort and Marina, just a quick 17-minute, direct ride to the fishing grounds, we ensure you get to the action fast. Join us for an unforgettable Key West fishing adventure—your perfect trip awaits!

The following features are on the High Stakes:

  1. Garmin GPS XSV 12 in. and Sonar capable of seeing down to 3,000 ft. (fish finder)
  2. Two private restrooms
  3. Two staterooms (one queen and two single beds)
  4. 4 air conditioning systems
  5. Spacious lounge (3 leather couches)
  6. Custom Tuna Tower
  7. Full Galley (refrigerator, microwave, sink and electric two burner glass cooktop)
  8. Redundant VHF radios
  9. Cellular telephone
  10. Twin 650 HP Caterpillar Engines 2019
  11. Daiwa Saltiga 50 Sailfish reel (6)
  12. Tanacom electric kite reels (2)
  13. Shimano Tiagra 30w (5)
  14. Shimano Tiagra 50w (4)
  15. Shimano Tiagra 80w (2)
  16. Hooker Electric Penn Internatonal 80w
  17. Custom matching Esky rods
  18. Shimano Saragosa 10000 spinning reels (4)
  19. Shimano Saragosa 6000 (4)
  20. Penn Fathom Master Downriggers
  21. Cockpit fishing station
  22. Live bait well
  23. Large fish box
  24. Pompanette Pro Series Fighting Chair
  25. Rupps Marine Tournament Outriggers
  26. Tanacom electric teaser system

Charters are available for up to a maximum of 6 people. You will find the accommodations clean and comfortable on your Key West fishing experience.

Meet the High Stakes Crew

We are a team of fishing professionals dedicated to making your Key West fishing charter successful AND memorable!

  • 2024 Sailfish tournament winners
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At High Stakes Charters, our father-son team, Don and Jason Jonas, are committed to delivering a professional and unforgettable fishing experience that combines years of expertise with personal dedication.
Don’s journey began when his family relocated from Connecticut to Key West. By the age of 16, he was already diving for legendary treasure hunter Mel Fisher. Over two decades with the Fishers, Don worked his way up to captain their 85′ dive vessel, the JB Magruder, solidifying his status as a seasoned mariner.
Captain Jason Jonas, born and raised in Key West, followed in his father’s footsteps. At just 18, he earned his Captain’s license, and with relentless passion, obtained the prestigious 100-ton Master Captain’s license. At 27, Jason made history as the youngest captain to win the Key West Marlin Tournament. His list of accomplishments continued to grow—he placed 3rd overall and 1st in the Mahi division in 2016, led his team to 2nd place in the 67th International Hemingway Marlin Tournament in 2017, and claimed 1st place in the Mahi division of the 2019 Key West Marlin Tournament. Most recently, in 2024, Captain Jason took 1st place in the Key West Sailfish Championship. Over the course of his career, he has earned over $200,000 in tournament prizes for his charters.
Their combined 35 years of fishing expertise have taken them to some of the world’s most stunning locations, including Cuba, Belize, Mexico, the Dominican Republic, the British Virgin Islands, and the Bahamas. With their deep knowledge of the local waters and commitment to excellence, you’re guaranteed the ultimate fishing adventure with High Stakes Charters.
Our first mate, Matt Bronson, originally from Jacksonville, recently celebrated his 6th year with High Stakes Charters. With 15 years of experience in Key West, Matt is known as the best mate in South Florida. Together, he and Captain Jason Jonas form an unbeatable team, combining their expertise and dedication to provide an exceptional fishing experience for every guest.

Book your Key West fishing charter now and let the fun begin!