High Stakes Charters

High Stakes Charters runs offshore fishing trips with style. These fishermen have over three decades of combined fishing experience, and can put you on a variety of fish swimming around the waters of Key West.

From novice to pro anglers, anglers fishing with High Stakes Charters come back to the shore with a grin. And rightly so. Here you can find Mahi Mahi, Tuna, Blue Marlin, Snapper, Grouper, Wahoo, Sailfish and many other pelagics and bottom fish. Just one glimpse around the photos, and you will understand why many fishermen come back to fish together with Don and Jason Jonas.

This father/son duo aims to give their guests an exciting and unforgettable day on the water. When he was 16, Don became a diver for a prominent treasure hunter, Mel Fisher, subsequently captaining the crew’s 85’ dive boat. Jason was born and raised in Key West, and decided early on to follow in his father’s footsteps. The crew’s passion and love for fishing saw them discovering and testing the waters of numerous famed fishing destinations, including Belize, Mexico, Dominican Republic, Bahamas and more.

High Stakes is a 53’ Striker Sportfisher powered by twin 650 HP Caterpillars, capable of cruising at 25 mph. She can take up to 6 fishermen. The boat is rigged with an array of navigational and fish finding technology, such as a Garmin 4210 GPS and Sonar, as well as VHF radios. The vessel features two private bathrooms and 4 ACs on board, as well as a spacious seating area, with 3 leather couches. The galley is equipped with a refrigerator, microwave and sink, as well as electric two-burner cooktop. There are two staterooms on board, with one queen and two single beds.

High Stakes Charters is located at Oceanside Marina, on the south side of the island. All fishing gear is provided, as well as the fishing license. Pack your camera, prepare food and snacks, bring sunblock, a cap, sunglasses, and comfortable clothes. Hop on and let High Stakes help you get that fish.



Select date to see available trips and rates:

  • Private trip
    Half Day Trip (AM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 7:30 AM
    $1,200
    This half day trip is a great package for novice anglers or families with kids. You will have just enough time to explore the fisheries on either side of Florida, depending on what you like, and target Mahi Mahi, Blue Marlin, Sailfish, Mahi Mahi, Wahoo, Blackfin Tuna. The fishing gear and license are supplied. Pack a camera, food and snacks, bring sunblock, a cap, sunglasses, comfortable clothes, and non-marking shoes. The crew will take care of the rest.
  • Private trip
    Half Day Trip (PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 1:00 PM
    $1,200
    Use the afternoon to explore rich fisheries that surround Florida. The target species are migratory fish such as Mahi Mahi, Blue Marlin, Sailfish, Wahoo, Blackfin Tuna. The fishing gear and license are provided. You should bring a camera, food and snacks, sunscreen, a cap, shades, comfortable clothes, and non-marking shoes. Departure time can vary slightly. The trip works great for those with a busy schedule, novice anglers, or families with minors.
  • Private trip
    3/4 Day Trip
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 7:30 AM
    $1,600
    This trip gives you more time, which means you might have better chances to land your dream catch. Offshore you can target Mahi Mahi, Blackfin Tuna, Blue Marlin, Sailfish, Wahoo, and more. The crew will supply the fishing gear, license, ice, bait, and will clean your catch. Bring a camera, sunblock, a cap, non-marking shoes, food and adult beverages, preferably in cans.
  • Private trip
    Full Day Trip
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 7:30 AM
    $2,000
    Hardcore anglers, this one is for you. You will have a full day to venture into the Gulf or Atlantic waters of Florida and target Mahis, Marlins, Sailfish, Blackfin Tuna, Wahoo, and other game swimming around. The crew will furnish the gear, tackle, license, bait, ice, bottled water, and soda, and will cover the fuel costs. You need to pack food, beverages (in cans), a cap, sunblock, a hat, non-marking shoes, and a camera.
  • Private trip
    Extended Full Day Trip
    FREE Cancellation 7 days notice
    10 Hour Trip, starts at 7:30 AM
    $2,400
    This trip is the ultimate offshore fishing around Key West. It's 10 hours of action, a big boat, and big game. The trip work best for accomplished and seasoned anglers. The crew will bring the gear, tackle, lures, bait, ice, water in bottles and soda, and will take care of the license. You should bring non-marking shoes, a cap, beverages in cans, sunblock, comfortable clothes to move easily, and a camera.
There are 13 people looking at this charter.

About the Captain

Jason Jonas
Key West, Florida, United States
ID & License verified
76 Customer Reviews
Response time 9 hours
Member since June 2014
The team behind High Stakes Charters is a father/son pair with several decades of combined fishing experience. Capt. Don became a diver for the world-famous treasure hunter Mel Fisher at an early age of 16. Working with them for two decades, he went on to captain their He 85’ dive boat, JB Magruder. Capt. Jason followed in his dad’s footsteps and earned his captain’s license at 18. They have worked on honing their skills and constantly try to further their fishing techniques. Back in 2008, at the Drambuie Marlin tournament, Capt. Jason landed a 350 lbs Marlin, followed by media coverage, interviews, and articles. The duo is focused, professional, and knows the waters intimately. Whatever your skillset, this crew will give their best to make your trip the unforgettable fishing experience.

About this listing

Targeted Species

Amberjack Amberjack
Barracuda (Great) Great Barracuda
Dolphin (Mahi Mahi) Dolphin (Mahi Mahi)
Grouper (Black) Black Grouper

Grouper (Goliath) Goliath Grouper
Little Tunny (False Albacore) Little Tunny (False Albacore)
Marlin (Blue) Blue Marlin
Marlin (White) White Marlin

Sailfish Sailfish
Snapper (Yellowtail) Yellowtail Snapper
Tuna (Blackfin) Blackfin Tuna
Wahoo Wahoo

Boat Specs

Striker (Offshore sport fishing) originally built in 1977, and restored in 2019. Powered by 2 650HP Caterpillar C8.7 engines, with a maximum cruising speed of 25 knots.

Length
53 ft
Capacity
6 persons

Types of Fishing

Nearshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Jigging
Drift Fishing
Kite Fishing
Deep Sea Fishing

Amenities

Toilet
Two private restrooms
Air Conditioning
Fighting Chair
Pompanette Pro Series
GPS
Garmin 4212
Fishfinder
Bed
Flybridge
Live Bait Well
Kitchen
Refrigerator
Multimedia System
Outriggers
Ice Box
Toilet
Two private restrooms
Air Conditioning
Fighting Chair
Pompanette Pro Series
GPS
Garmin 4212
Fishfinder
Bed

Trip Includes

Rods, reels & tackle
mainly Penn and Shimano
Lures
Catch cleaning & filleting
Drinks
Soft drinks & water
First Mate
Fishing License

Cancellation Policy

Free cancellation up to 7 days prior to trip

Customers can cancel or modify their booking up to 7 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

Listing Policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed
Disabled Accessible

Payment

Book with 10% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Visa
Mastercard
American Express
When paying the remaining balance with a credit card, an additional 4% charge will apply.

Key West Fishing Calendar

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Customer Reviews

Rating Summary
Photos & videos by reviewers (96)
Excellent
4.8 / 5
out of 5 stars from 76 reviews
Boat
Excellent
4.8 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Big Timin and catchin monsta\u2019s on the High Stakes
Half day trip
Half day trip
+93
Angler Rating
67
6
1
1
0
Anglers Claimed
Good experience
94%
Friendly captain
100%
Recommend this charter
96%
Appropriate for children
88%
Satisfied with the boat
98%
Catch intended fish
81%
Sort By:
Featured  
Showing:
5 of 76 reviews
Emily H.
Key West, Florida
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

3/4 Day

VERIFIED   3/4 Day Trip on February 12, 2022
What a fabulous experience! Capt and first mate made our group of 4 feel right at home. Very knowledgeable, accommodating,...
Emily H. recommends High Stakes Charters
Mark review as helpful
You found this review helpful
  Jason Jonas Captain replied

Joseph A.
Miami, Florida
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

3/4 Day Trip with Captain Jason and first mate Matt

VERIFIED   3/4 Day Trip on June 21, 2021
We had the most amazing trip! I took the time to research for a first class captain and a very successful first mate, the crew...
Joseph A. recommends High Stakes Charters
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You found this review helpful
  Jason Jonas Captain replied

Sean F.
Miami, Florida
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip

VERIFIED   Half Day Trip (AM) on February 10, 2022
The crew were friendly and did their best to help us catch some fish. We each caught a barracuda and had fun despite the fact...
Sean F. recommends High Stakes Charters
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You found this review helpful
  Jason Jonas Captain replied

Charles S.
Fort Lauderdale, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip

VERIFIED   Half Day Trip (PM) on February 26, 2022
The guys at High Stakes are very professional while still being laid back. We really enjoyed our charter.
Charles S. recommends High Stakes Charters
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You found this review helpful
  Jason Jonas Captain replied

Jeff P.
Fort Smith, AR
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Jason

VERIFIED   Half Day Trip (AM) on February 25, 2022
Jeff P. recommends High Stakes Charters
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You found this review helpful
  Jason Jonas Captain replied

FAQs about High Stakes Charters

High Stakes Charters offers the following trips to customers:
  • $1,200 per group - Half Day Trip (AM) (4 hours)
  • $1,200 per group - Half Day Trip (PM) (4 hours)
  • $1,600 per group - 3/4 Day Trip (6 hours)
  • $2,000 per group - Full Day Trip (8 hours)
  • $2,400 per group - Extended Full Day Trip (10 hours)

When you book a trip with High Stakes Charters, you can expect the following amenities onboard:
  • Toilet (Two private restrooms)
  • Air Conditioning
  • Fighting Chair (Pompanette Pro Series)
  • GPS (Garmin 4212)
  • Fishfinder
  • Bed
  • Flybridge
  • Live Bait Well
  • Kitchen
  • Refrigerator
  • Multimedia System
  • Outriggers
  • Ice Box

Trips booked with High Stakes Charters include:
  • Rods, reels & tackle (mainly Penn and Shimano)
  • Lures
  • Catch cleaning & filleting
  • Drinks (Soft drinks & water)
  • First Mate
  • Fishing License

High Stakes Charters offers the following types of fishing:
  • Nearshore Fishing
  • Offshore Fishing
  • Reef Fishing
  • Wreck Fishing

High Stakes Charters offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Spinning
  • Jigging
  • Drift Fishing
  • Kite Fishing
  • Deep Sea Fishing

Top targeted fish species with High Stakes Charters include:
  • Amberjack
  • Barracuda (Great)
  • Dolphin (Mahi Mahi)
  • Grouper (Black)
  • Grouper (Goliath)
  • Little Tunny (False Albacore)
  • Marlin (Blue)
  • Marlin (White)
  • Sailfish
  • Snapper (Yellowtail)
  • Tuna (Blackfin)
  • Wahoo