About Your Guide

Jackson Tomaszewski

Independent Guide
My name is Jackson, a lifelong resident of Hilton Head Island. As a passionate navigator of the seas and dedicated Captain on a quest to elevate the maritime experience, I look forward to any extraordinary opportunities and adventures.

About Your Guide

Jackson Tomaszewski

Independent Guide
My name is Jackson, a lifelong resident of Hilton Head Island. As a passionate navigator of the seas and dedicated Captain on a quest to elevate the maritime experience, I look forward to any extraordinary opportunities and adventures.
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Inshore Fishing

NEW 1 - 2 People 3 - 7 Hours From $375
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing
Inshore Fishing

About Your Trip

Water Type

Inshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather

Step aboard with Captain Jackson and get ready to experience the wild beauty of Hilton Head Island’s inshore waters like never before! As a lifelong resident and passionate seafarer, Captain Jackson brings deep local knowledge and an easygoing, expert approach to every trip. Whether you're a seasoned angler or brand new to fishing, this adventure is all about enjoying the moment, learning the local waters, and reeling in some of the Lowcountry’s most sought-after species....

About Your Trip

Step aboard with Captain Jackson and get ready to experience the wild beauty of Hilton Head Island’s inshore waters like never before! As a lifelong resident and passionate seafarer, Captain Jackson brings deep local knowledge and an easygoing, expert approach to every trip. Whether you're a seasoned angler or brand new to fishing, this adventure is all about enjoying the moment, learning the local waters, and reeling in some of the Lowcountry’s most sought-after species.

Your trip takes place aboard a well-equipped 26’ Grady White, powered by twin engines for a smooth, stable ride through Hilton Head’s incredible backcountry. This estuarine network of winding tidal creeks, marshes, and shallow flats is teeming with life—and it's one of the best spots in the Southeast for light tackle fishing. These calm, protected waters make for a perfect day on the rod, whether you're casting solo, bringing the family, or just looking to relax and reel in something worth bragging about.

Depending on the season and conditions, you’ll be targeting a variety of inshore favorites like Redfish, Speckled Sea Trout, Black Drum, and Flounder. Using light tackle setups, you'll get the thrill of the fight without the need for heavy gear, making every hookup a hands-on, heart-pounding experience. Captain Jackson will tailor the trip to your experience level and interests, and he's happy to share tips and stories from a lifetime spent navigating these waters.

Trips are offered in flexible durations, so whether you’re looking for a quick morning getaway or a half-day of serious casting, there’s a trip to match your schedule. Everything you need—rods, reels, tackle, bait, and licenses—is provided, so just bring your favorite snacks, weather-appropriate clothing, and a sense of adventure.

With its peaceful setting, abundant wildlife, and incredible inshore action, this Hilton Head light tackle trip offers the perfect way to connect with nature, catch some fish, and experience the Lowcountry through the eyes of a true local. Captain Jackson is excited to welcome you aboard!
Amenities

Water Type

Inshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Weather

You won’t lose your deposit if the trip is canceled due to weather

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Boat Restroom

No, this boat does not have a bathroom on board.

Live Bait

Live bait is not used on this trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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About Your Boat

Boat photo for Inshore Fishing
Boat Type
Catamaran
Boat Manufacturer
Glacier Bay
Boat Length
26'
Boat Restroom
No

About Your Boat

Boat Type
Catamaran
Boat Manufacturer
Glacier Bay
Boat Length
26'
Boat Restroom
No
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Potential Target Species

Color-coded seasonality below is based on .
View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Cut Bait Fishing
Drift Fishing
Light Tackle Fishing

Type of Fishing

Need a Place to Stay?

Captain Hilton Head Photo Gallery

Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 30th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 15th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 30th, 2025
Hilton Head Island, South Carolina
Inshore Fishing
October 30th, 2025
Hilton Head Island, South Carolina
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