Cheshire Cat Fishing Charters

Cheshire Cat Fishing Charters welcomes you with a smile and invites you to spend the day fishing for great inshore and nearshore species in the warm waters of the Gulf of Mexico. Wrestle with big bull Redfish, hard-fighting Seatrout, delicious Sheepshead, and much more inshore, or head up to nine miles out in search of reef fish like Snapper, Triggerfish, Grouper, and Amberjack.

You will be fishing aboard Captain Kevin’s 23’ Robalo bay boat. This versatile vessel is perfect for navigating the local shallows but can still hold her own in the choppy waters a few miles out. She is equipped with the latest electronics and plenty of equipment to target the area’s many fish species.

When fishing inshore, the boat’s trolling motor will let you sneak stealthily towards the best spots without spooking all the fish. Head out to the reefs, and her fishfinder and radar will sweep the depths in search of structure and big fish, making sure you have as much time fishing as possible. The boat also features a tower, that will make fish spotting much easier.

Wherever you spend your trip, you will be fishing with an experienced guide with over 20 years fishing Destin’s local waters. Captain Kevin loves to work with experienced anglers and complete beginners alike. He will tailor your trip to suit your needs and make sure you get exactly what you want from your time onboard.

All trips come with everything you will need for the fishing itself. Just bring your food, any drinks you want for the day, and plenty of energy for a great day’s fishing!



Select date to see available trips and rates:

  • Private trip
    10 Hour Trip – Inshore/Offshore
    FREE Cancellation 1 day notice
    10 Hour Trip, starts at 6:00 AM
    $1,250
    up to 5 persons
    Spend the whole day on the water, up to 9 miles out, fishing up to 9 miles out for Redfish, Spanish and King Mackerel, Snapper, Grouper, Mahi-Mahi, and more. With the added hours, you are sure to bring home dinner for you and your friends.
  • Private trip
    8 Hour Trip – Inshore/Offshore
    FREE Cancellation 1 day notice
    8 Hour Trip, starts at 6:00 AM
    $1,000
    up to 5 persons
    Spend the whole day on the water, fishing up to 9 miles out for Redfish, Spanish and King Mackerel, Snapper, Grouper, Mahi Mahi, and more. With the added hours, you are sure to bring home dinner for you and your friends.
  • Private trip
    6 HOUR RED SNAPPER 3 WEEKENDS ONLY
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 6:00 AM
    Seasonal trip Oct 1 - Oct 26 (Sat, Sun)
    $900
    up to 5 persons
    HURRY AND BOOK BEFORE OCTOBER 26TH
  • Private trip
    6 Hour Trip – Inshore/Offshore (AM)
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 6:00 AM
    $900
    up to 5 persons
    Inshore/offshore: Fish up to 9 miles out for Redfish, Spanish and King Mackerel, Snapper, Grouper, and more. With the added 2 hours, you are sure to be bringing home your whole family dinner tonight.
  • Private trip
    6 Hour Trip – Inshore/Offshore (PM)
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 1:00 PM
    $900
    up to 5 persons
    Inshore/offshore: fish up to 9 miles out for Redfish, Spanish and King Mackerel, Snapper, Grouper, and more. With the added 2 hours, you ar sure to be bringing home your whole family dinner tonight.
  • Private trip
    6 HOURS FOR RED SNAPPER 3 WEEKENDS
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 1:00 PM
    Seasonal trip Oct 1 - Oct 26
    $900
    up to 5 persons
    HURRY AND BOOK BEFORE OCTOBER 26TH
  • Private trip
    3 WEEKENDS ONLY RED SNAPPER
    FREE Cancellation 1 day notice
    5 Hour Trip, starts at 6:00 AM
    Seasonal trip Oct 1 - Oct 26 (Sat, Sun)
    $750
    up to 5 persons
    FOR ONLY 3 WEEKENDS IN OCTOBER, STATE BOATS ARE PERMITTED TO CATCH RED SNAPPER. HURRY AND BOOK BEFORE IT'S GONE!!!!!
  • Private trip
    5 Hour – Inshore/Offshore (AM)
    FREE Cancellation 1 day notice
    5 Hour Trip, starts at 6:00 AM
    $750
    up to 5 persons
    FISH UP TO 9 MILES OUT FOR REDFISH, SPANISH AND KING MACKEREL, MINGOS, GROUPER, AND MORE. WITH THE ADDED HOUR, YOU ARE SURE TO BRING HOME DINNER.
  • Private trip
    5 Hour – Inshore/Offshore (PM)
    FREE Cancellation 1 day notice
    5 Hour Trip, starts at 1:00 PM
    $750
    up to 5 persons
    FISH UP TO 9 MILES OUT FOR REDFISH, SPANISH AND KING MACKEREL, MINGOS, GROUPER, AND MORE. WITH THE ADDED HOUR, YOU ARE SURE TO BRING HOME DINNER.
  • Private trip
    5 HOUR 3 WEEKEND ONLY RED SNAPPER
    FREE Cancellation 1 day notice
    5 Hour Trip, starts at 12:00 PM
    Seasonal trip Oct 1 - Oct 26 (Sat, Sun)
    $750
    up to 5 persons
    HURRY AND BOOK BEFORE OCTOBER 26TH
  • Private trip
    Half Day – Inshore/Offshore (AM)
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 6:00 AM
    $600
    up to 5 persons
    Fish the local waters up to 9 miles for Redfish, Snapper, Kong’s, Mingos, Tarpon, and much more on this four-hour morning trip.
  • Private trip
    Half Day – Inshore/Offshore (PM)
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 1:00 PM
    $600
    up to 5 persons
    Head out up to 9 miles out for Redfish, Snapper, Kingfish, Mingos, Tarpon, and much more on this four-hour afternoon trip.
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About the Captain

Tyler Brielmayer
Destin, Florida, United States
Angler's Choice
10 Fishing Reports
71 Customer Reviews
Response time within an hour
Member since January 2018
Fishing has been my passion since I was a very young boy. I was on my first boat at 6 months of age and began fishing in different locations all over the world from the age of 5. I have lived in Destin my whole life and rarely spent a weekend off the water. I even fished when I worked offshore on the oil rigs. The water is where I am the happiest and most relaxed. I got my captain license so I could share my knowledge and passion for fishing with everyone who steps aboard. My goal is to give everyone the fishing trip of a lifetime.

About this listing

Targeted Species

Cobia
Grouper (Gag)
King Mackerel (Kingfish)
Redfish

Sheepshead
Snapper (Red)
Spanish Mackerel
Speckled Trout

Tarpon

Boat Specs

Robalo (Center console) originally built in 2015. Powered by a 200HP Yamaha engine, with a maximum cruising speed of 25 knots.

Length
23 ft
Capacity
5 persons

Types of Fishing

Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing
Flats Fishing
Backcountry Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging
Bowfishing
Flounder Gigging
Deep Sea Fishing

Amenities

Toilet
GPS
Life Jackets
Fishfinder
Live Bait Well
Wireless Trolling Motor
Ice Box
Toilet
GPS
Life Jackets
Fishfinder
Live Bait Well
Wireless Trolling Motor

Trip Includes

Rods, reels & tackle
Lures
Catch cleaning & filleting
Fishing License

Policies

FREE Cancellation
You can cancel or change your booking free of charge up to 1 day before the trip date. 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

Payment

Book with 20% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 20% 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 3% fee.

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Customer Reviews

Rating Summary
Photos by reviewers (25)
4.46
out of 5 stars from 49 reviews
Boat
Crew
Experience
Great Trip.....Again!
Half day trip with Captain Andy Hoolister
Had an awesome 8 hour trip with captain Kevin on the Cheshire cat.
+22
Angler Rating
37
4
4
3
1
Anglers Claimed
Good experience
82%
Friendly captain
94%
Recommend this charter
82%
Appropriate for children
83%
Satisfied with the boat
89%
Catch intended fish
79%
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Showing:
5 of 49 reviews
Shawn M.
Duluth, GA
 5.00
Experience:
Boat
Crew
Overall
Man what trip! Captain Kevin had us on kings before we were done catching bait. We limited on king mackerel in 3 hours and...
Shawn M. recommends Cheshire Cat Fishing Charters
Mark as helpful
You found this helpful
  Tyler Brielmayer Captain replied

Kyle E.
Walker, LA
 5.00
Experience:
Boat
Crew
Overall

Great Trip.....Again!

VERIFIED   NEW  November 29, 2019
Another great fishing trip with Cheshire Cat. Kevin was awesome, always works hard to make the trip memorable. We went fishing...
Kyle E. recommends Cheshire Cat Fishing Charters
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Kyle E. recommends Cheshire Cat Fishing Charters
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Amanda M.
Minersville, Pennsylvania
 5.00
Experience:
Boat
Crew
Overall

Half day trip with Captain Andy Hoolister

VERIFIED   August 23, 2019
Captain Andy took us around Destin, he was friendly and knowledgeable,  informative and instructive and overall a seriously...
Amanda M. recommends Cheshire Cat Fishing Charters
Mark as helpful
You found this helpful
  Tyler Brielmayer Captain replied

Terry A.
Winder, GA
 5.00
Experience:
Boat
Crew
Overall

Half day with Captain Kevin

VERIFIED   July 24, 2019
This was our first chartered fishing experience.  However, it will not be our last.  Captain Kevin was great! ...
Terry A. recommends Cheshire Cat Fishing Charters
Mark as helpful
You found this helpful
  Tyler Brielmayer Captain replied

Rebecca K.
Gulf Breeze, Florida
 4.67
Experience:
Boat
Crew
Overall

Half Day Trip with Captain Kevin

VERIFIED   October 8, 2019
Truly a fantastic experience. We are a family of newbies, and Kevin was patient and kind with us and really went out of his...
Rebecca K. recommends Cheshire Cat Fishing Charters
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Rebecca K. recommends Cheshire Cat Fishing Charters
Mark as helpful
You found this helpful