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Key West Charter Fishing – Deep Sea Tournament Fishing

High Stakes Charters offers deep sea fishing in Key West, Florida. Enjoying the magnificant waters off the Keys while catching fish is the perfect vacation! Key West offers incredible fishing grounds just a few miles offshore.

High Stakes Charters offers a variety of options for your stay in the Florida Keys. Whether you are looking for a day of fishing with your friends and family or a relaxing sunset cruise in Key West, High Stakes will make your trip memorable.

Captain Jonas is a well experienced captain and has fished off the waters of the Florida Keys for many years. He is trained, licensed and his talents are called upon daily. Learn more here.

Make High Stakes Charters your number one priority if you want to catch fish in the deep waters off Key West…

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 .

John K.

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!

John RLongmont, CO

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.

Jeane DrakeLondonderry, OH

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.

Stephanie W.Chicago, IL

Ready For Deep Sea Fishing?

Our top reviews demonstrate the expertise and dedication we have for our profession.  If you are ready to treat yourself to an incredible, one-of-a-kind deep sea fishing experience in Key West, FL we entice you to try High Stakes Charters!

From our immaculate 53′ Striker Sport fishing vessel to our extensive experience fishing on the high seas we will make your fishing experience second to none!

Call us to reserve your charter today!

(305) 294-8040

What others say about us

Christine A

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.

Christine A

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!

MFrostySan Antonio, TX
Eric C

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

Eric CChicago
Mark T

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.

Mark TKey West, FL



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