Maryland Chesapeake Bay Charter Fishing

Free cancellation
Tenacious Fishing Charters is Captained by 3rd generation Charter captain, Capt. Jacob Henderson. We are a family owned and operated Chesapeake Bay Charter for Striped Bass (more locally known as Rockfish) as well as other species such as Bluefish, Spanish Mackerel, Cobia and Red Drum. We also do some bottom fishing for Spot, Perch and Croakers. We've even caught some Catfish! We specialize in family/friends charters and company outings. We take a very versatile approach to our fishing as we offer trolling, jigging, live baiting and bottom fishing. It is not uncommon to do a little of each on a day trip! If you have any further questions, please contact Capt. Jacob by phone or text at (410) 353-8636, or by email at We look forward to getting you out on the Chesapeake Bay for a fishing trip you'll never forget!


Check dates with the Operator
We recommend checking dates with the Captain before booking your trip.


Trip Includes
Fishing license

Trip does NOT Include
Minimum 20%tip for mate. Fish cleaning is available @ additional cost

You keep catch


Free cancellation (14 days in advance).
Cancellation Policy - We require a minimum of 14 days notice to cancel or reschedule a charter using the applied deposit. Failure to do so will forfeit your deposit. Foul Weather Policy - In the event of inclement weather or the forecast of inclement weather, unless contacted by Captain Jacob you are required to show up on the date of the charter. If it is determined by Captain Jacob that the weather is too bad, your deposit will be applied to a later date.


Striped Bass
Red Drum
Spanish Mackerel

Types of Fishing
Chesapeake Bay Fishing
Inshore fishing
Nearshore fishing
River fishing
Wreck fishing

Fishing Techniques
Drift fishing
Light tackle
Live lining
Heavy tackle
Bottom fishing
Bow fishing
Handline fishing

Tackle box
Fish finder
Fishing Pole
Rod holders
Rods & Reels

Boat Specs

Offshore boat

Offshore boat (Baybuilt) originally built in 2003. Powered by 1 engine (450HP, Cummins), with a maximum cruising speed of 28 knots.
42 ft
Services And Facilities
Furuno Radar
Air Conditioning
Trolling rods
Life Jacket



Jacob Henderson

Operator since 2004
Capt. Jacob is a third-generation captain. He has spent the majority of his life fishing and learning the ropes from his Dad and Grandfather. He has a passion for all things fishing, it’s infectious. Jacob began mating for his Dad when he was just seven years old. Ironically, his Dad is now his first mate on the Tenacious. As a young kid, Jacob would spend his weekends, school holidays and any free time he had fishing and working on boats. In 2002, Jacob missed the morning of Opening Day of Rockfish season to sit for his United States Coast Guard Captain’s License exam. He was back on the dock, ready to run the boat by that afternoon. He holds a 100 Ton Near Coastal and Inland Masters, a Marine Radio Operators Permit and a Transportation Workers Identification Credential (TWIC) card. Growing up in Shady Side, MD has not only made the Chesapeake Bay his home away from home, but has allowed Jacob to work for multiple captains and boats in the area which has given him the opportunity to gain different techniques and skills.

Jacob Henderson

Operator since 2004

How to get there

Deale, Maryland, United States

Book with 25% deposit

Once the charter confirms your trip, your credit card will be charged with a 25% deposit to guarantee the reservation.

Pay remaining balance to the captain

The remaining balance will be paid directly to the charter on the trip date. The following payment methods are available: