High Stakes Charters

5950 Peninsular Ave
Key West FL, United States

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 Charters is a 53’ Striker Sportfisher powered by twin Detroit 871 twin turbo diesel engines. 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 (fish finder), 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
    Extended Full Day Trip
      FREE Cancellation 3 days notice
    10 hours trip, starts at 7:30 AM
    US$ 1800
    up to 6 persons
    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.
  • Private trip
    Full Day Trip
      FREE Cancellation 3 days notice
    8 hours trip, starts at 7:30 AM
    US$ 1500
    up to 6 persons
    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
    3/4 Day Trip
      FREE Cancellation 3 days notice
    6 hours trip, starts at 7:30 AM
    US$ 1200
    up to 6 persons
    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
    Half Day Trip (AM)
      FREE Cancellation 3 days notice
    4 hours trip, starts at 7:30 AM
    US$ 900
    up to 6 persons
    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 3 days notice
    4 hours trip, starts at 1:00 PM
    US$ 900
    up to 6 persons
    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
    Sunset Cruise
      FREE Cancellation 3 days notice
    3 hours trip, starts at 5:00 PM
    US$ 550
    up to 6 persons
    This trip is a nice ride around the harbor, with no fishing involved. It's a good chance to unwind and enjoy the view. It is great for families with kids, or groups of friends wishing to celebrate an important event. The boat is spacious and stable, which means you will enjoy a smooth ride. The departure time is usually some two hours prior to the sunset. The view can be breathtaking. Grab some snacks and beverages, a sunblock, cap, and comfortable clothes.
There are 4 people looking at this charter.

About this listing

Targeted Species

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

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

Sailfish
Snapper (Yellowtail)
Tuna (Blackfin)
Wahoo

Boat Specs

Striker (Offshore sport fishing) originally built in 1977, and restored in 2017. Powered by 2 1000HP Detroit 8V-71 engines.

Length
53 ft
Capacity
6 persons

Types of Fishing

Nearshore Fishing
Offshore Fishing
Wreck Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging
Drift Fishing
Kite Fishing

Amenities

Toilet
Air Conditioning
Fighting Chair
GPS
Life Jackets
Fishfinder
Bed
Flybridge
Live Bait Well
Kitchen
Refrigerator
Multimedia System
Outriggers
Ice Box
Toilet
Air Conditioning
Fighting Chair
GPS
Life Jackets
Fishfinder

Trip Includes

Rods, reels & tackle
Lures
Catch cleaning & filleting
Drinks
First Mate
Fishing License Included

Policies

FREE Cancellation
You can cancel or reschedule your booking up to 3 days before the trip. If the captain cannot run the trip due to unsafe weather conditions, your booking can be moved to another date or canceled free of charge.
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
When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.
Pay remaining balance to captain
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, there is a 4% fee.

About the Captain

Jason Jonas
Key West, Florida, United States
Member since June 2014
38
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.
Response time: 1 hour
Response rate: 97%

Key West Fishing Calendar

Loading Fish Calendar!
Please Wait...

Customer Reviews

Rating Summary
Photos by reviewers (40)
4.79
out of 5 stars from 38 reviews
Boat
Crew
Experience
August fishing trip
Morning fishing with Captain Don and Mate Shawn
Morning fishing with Captain Don and Mate Shawn
+37
Angler Rating
32
5
1
0
0
Anglers Claimed
Good experience
90%
Friendly captain
100%
Recommend this charter
97%
Appropriate for children
86%
Satisfied with the boat
100%
Catch intended fish
68%
Sort By:
Featured  
Showing:
5 of 38 reviews
Michelle Madrid
Aurora, CO
 5.00
Experience:
Boat
Crew
Overall

3/4 day trip was a blast

VERIFIED   July 15, 2018
This was the best part of our entire 6 day trip!!! Don and Heath were awesome!  Taught this girl a lot!!! ...
Michelle Madrid recommends High Stakes Charters
Mark as helpful
You found this helpful
  Jason Jonas Captain replied

Tyler Myers
Sheridan, Wyoming
 5.00
Experience:
Boat
Crew
Overall

A Fisherman Must Do!

VERIFIED   June 1, 2018
Our trip took place a couple of days after a tropical storm, so the fishing was scarce, but that didn’t stop our crew...
Tyler Myers recommends High Stakes Charters
Mark as helpful
You found this helpful
  Jason Jonas Captain replied

Rose Lee
United States
 5.00
Experience:
Boat
Crew
Overall

Morning fishing with Captain Don and Mate Shawn

VERIFIED   July 23, 2018
Excellent morning of deep sea fishing.  Caught enough Wahoo and Mahi mahi to feed six of us and to eat for a week straight. ...
Rose Lee recommends High Stakes Charters
Mark as helpful
You found this helpful
  Jason Jonas Captain replied

Dan Walker
United States
 5.00
Experience:
Boat
Crew
Overall

Full Day

VERIFIED   July 2, 2018
We had a really great full day, a little breeze, but not too choppy. We kept 12 fish that Sean (our deck hand) cleaned for...
Dan Walker recommends High Stakes Charters
Mark as helpful
You found this helpful
  Jason Jonas Captain replied

Alexander Gaidarski
United States
 5.00
Experience:
Boat
Crew
Overall

Fishing with Jason

VERIFIED   August 19, 2018
Wonderful experience
Alexander Gaidarski recommends High Stakes Charters
Mark as helpful
You found this helpful
  Jason Jonas Captain replied