Chester Fishing Charters

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 an incredible day-long fishing trip with an amazing captain who went above and beyond to ensure everyone had a fantastic time." —⁠ Keith,

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.

"Great boat completely prepared and captain was great helping our entire group be prepared for fishing excursion." —⁠ Edmund,

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,

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

"Had a great time with Charlie and Jeff. We were on fish immediately." —⁠ Khem,

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.

"The wind was pretty strong and so was the current. Capt. Marion never stopped trying to find us a hotspot." —⁠ JD,

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,

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.

"We took our kids and grandparents out for a great day on the water." —⁠ Charles,

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.

"If you’re considering this fishing charter, just take the bait and book!" —⁠ Pam,

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.

"Things got off to a great start. Captain went over a few things, asked us what we wanted and expected for the day." —⁠ Ray,

Mallard Charters is located in Stevensville, MD and offers to show you a memorable time on the Chesapeake Bay. Capt. Troy will make sure you have a fun day full of fishing.

"Captain Troy was very knowledgable and professional.  We tried for rockfish at the bay bridge and Sandy Point lighthouse but not much was biting." —⁠ Christopher,