Chester Fishing Charters

The best out of 91 charter fishing deals in Chester - enter dates to check availability

Chester Fishing Charters

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Top Fishing Charters in Chester

Chester: 91 fishing charters available

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Angler's Choice
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42 ft
Up to 6 people
JadeLady Charters
4.9
/5
(137 reviews)
Stevensville (14 min drive from Chester)
Operating out of Stevensville, JadeLady Charters specialize in inshore fishing and crabbing. They are located on Maryland's eastern coast, at Kentmorr marina, fishing the magnificent Chesapeake Bay, home of the Striped Bass and Maryland Blue Crab.

"Took 6 of us out for a morning fishing charter including three children." —⁠ Matthew,
trips from
US $625
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32 ft
Up to 6 people
Just For Fun Too Charters
4.8
/5
(18 reviews)
Grasonville (5 min drive from Chester)
Spend a lovely day on the water and enjoy unforgettable fishing moments with Just For Fun Too Charters. Starting out of Grasonville, you and Captain Jeffrey Councill will head out to the inshore waters of Maryland and have fun chasing many prized fish.

"Our family of 4 had a fabulous time on the morning finishing trip." —⁠ Mariya,
trips from
US $600
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46 ft
Up to 6 people
Biff Fishing Charters
5.0
/5
(125 reviews)
Stevensville (14 min drive from Chester)
Located on Kent Island, Biff Fishing Charters offers trips fishing for Striped Bass and Bluefish in the Chesapeake Bay. Captain Justin Kaufman has been fishing these waters for more than a decade and knows the area like the back of his hand.

"We had a great time on the water. Justin and Sean were very helpful and knowledgeable." —⁠ Ken,
trips from
US $640
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40 ft
Up to 6 people
CB Charters
5.0
/5
(64 reviews)
Chester
Chesapeake Bay is known for being home to one of the most sought-after species in the world – Striped Bass! If you're a hardcore angler who's always dreamed of chasing Stripers, or want to take your family on an exciting adventure explor

"Charlie was responsive, punctuate and friendly. He knew where all the fish were." —⁠ Fei,
trips from
US $700
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33 ft
Up to 6 people
PrimeTime Charters
4.9
/5
(352 reviews)
Stevensville (14 min drive from Chester)
Enjoy a nice day on the waters off the coast of Maryland with PrimeTime Charters! Captain Darnell Greenway has been fishing since he was a child and has a genuine passion for it.

"We had the pleasure of sailing with Darnell. He was very pleasant from the moment we arrived on the boat until the very end." —⁠ Nicole,
trips from
US $525
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25 ft
Up to 6 people
Reel Cool Charters Llc
5.0
/5
(10 reviews)
Grasonville (4 min drive from Chester)
Reel Cool Charters Llc runs angling trips out of Chester and offers to show you what the local fishery is all about. Capt. Michael will do his best to make sure you have a fun day full of fishing.
trips from
US $600
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25 ft
Up to 4 people
Nauti Hooker Charters – Stevensville
4.8
/5
(77 reviews)
Stevensville (16 min drive from Chester)
Explore secret fishing spots in the Chesapeake Bay with Nauti Hooker Charters! Captain Richard Phippin has been fishing in the area since he was a teenager and started this charter as a family business.

"I booked this trip for my husbands birthday as a gift! hom and two of his friends had the best time!" —⁠ Ashley,
trips from
US $450
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48 ft
Up to 18 people
Maryland Fishing and Hunting
5.0
/5
(122 reviews)
Stevensville (16 min drive from Chester)
Welcome aboard The Marylander! Maryland's premier charter boat on the Chesapeake Bay. We are located on Maryland's Eastern Shore, in Stevensville, MD. This is just outside of Annapolis, Baltimore, and Washington D.C.

"We had an excellent time with our friends and specially with my son, it was his first fishing trip and he had a great time!" —⁠ Alex,
trips from
US $960
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32 ft
Up to 6 people
Tight Times Charters
4.8
/5
(39 reviews)
Edgewater (37 min drive from Chester)
Tight Times Charters offers a variety of charters, including sport fishing, cruises, Blue Angels demonstrations, and parties. The professional captain and crew know all the hotspots to put you on the fish.

"We booked the 3-hour fishing tour with Tight Times for my son’s 11th birthday, and it was an unforgettable experience!" —⁠ Andrea,
trips from
US $450
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30 ft
Up to 6 people
Rock On Fishing
4.9
/5
(53 reviews)
Annapolis (15 min drive from Chester)
VOTED FISH BOOKERS ANGLERS'S CHOICE AWARD 3 YEARS IN A ROW! 2022-2024                     31 FIVE STAR REVIEWS CREATE GREAT FAMILY AND FRIENDS MEMORIES       Looking to catch some fish?

"Captain Mike was great! He communicated very well and let us know ahead of time that the meeting location had changed due to weather." —⁠ Kyle,
trips from
US $595

Top deep sea fishing trips in Chester

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Half-day fishing trips in Chester

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Frequently Asked Questions about Fishing Charters in Chester

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Fishing in Chester

Chester, Maryland, offers premier fishing adventures in the heart of the Chesapeake Bay. Its crown jewel, the Chester River, teems with striped bass (rockfish), perch, and catfish, providing year-round opportunities for anglers. Sheltered waters make it ideal when the main bay is rough, ensuring reliable fishing conditions. Spring brings trophy-sized stripers, summer delivers diverse catches including rockfish and crabbing, while fall excels for trolling.

Kent Narrows serves as the central hub for charters, with easy access to prime spots like Simkins Dam's reefs and oyster bars that attract baitfish and predators. Local captains leverage generations of knowledge to guide you to hidden hotspots, whether targeting schooled stripers downriver or feisty catfish upstream. Family-friendly outings and expert-led trophy hunts cater to all skill levels.

Charters supply top-tier gear and techniques tailored to the season—from light-tackle trolling to bottom rigging for perch. Beyond striped bass, expect surprises like Spanish mackerel or red drum. With its rich structure and abundant species, Chester remains a Chesapeake highlight where every trip promises action.

Chester

4.9
/5
Based on 30,571 reviews by FishingBooker anglers

Chester Fishing Calendar

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Recent Catches in Chester

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What anglers said about fishing in Chester

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How did anglers rate fishing charters in Chester?

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Nearby Fishing Destinations

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