533 Deale Road
Deale, Maryland 20751
Leaving from Happy Harbor Restaurant
Chesapeake Bay Maryland Sport Fishing Charters and Party Cruises

Chesapeake Bay Maryland Sport Fishing Charters and Party Cruises

Click Here to Make a Deposit on Your Fishing Charter

Obsession 45 Sport Fishing is a Deale Maryland based charter sport fishing and cruise business that takes you out into the world renowned Chesapeake Bay. We fish in saltwater bringing you trophy sport fishing for all you hard core anglers or just a fun day in the sun fishing with the family or with all of your colleagues and customers from the office or business world.

We also can provide cruising charters, waterfront restaurant dinner cruises, wedding ceremonies and scenic Chesapeake Bay cruises.

Chesapeake Bay MD Sportfishing

Our Captain

Captain Bobby “Mack” McCormack leads our crew to waters he has fished for 35 years. He has 30 years of commercial waterman experience fishing and crabbing the Chesapeake Bay. He has fished the Chesapeake Bay since he was 10 so he knows how to land the big trophy fish. You cannot go wrong with Captain Mack and his experience because you and your party will have the best fishing charter of the year. If there is one thing Captain Mack loves more than fishing himself, it is seeing his fellow anglers catch a lot of fish and go home happy.

Our Boat

Captain Mack not only leads our fishing charters and cruises but custom built his own boat called Obsession as well. Click here to see pictures.

The Obsession is a twin engine Coast Guard approved and inspected charter fishing boat that can accommodate fishing, company or wedding parties or groups of all sizes from six to a party of up to 25 anglers.

Family outing sportfishing R

Our Location

We are located in Deale, Maryland currently leaving from Happy Harbor Restaurant. Our charter boat serves the Maryland middle Chesapeake Bay and entire Chesapeake Beach region including Chesapeake Beach, Annapolis MD, middle Chesapeake Bay, and Calvert County MD.

We are convenient to anyone living or visiting the communities in Calvert County MD including: Barstow, Broomes Island, Chesapeake Beach, Deale, Dowell, Dunkirk, Huntingtown, Lusby, North Beach, Owings, Port Republic, Prince Frederick, St. Leonard, Solomons Island or Sunderland.

We are about 40 miles from Washington DC, 30 miles from Annapolis MD and 33 miles from Solomon's Island.

Chesapeake Bay Fish Species We Fish for and When

On our Chesapeake Bay Charter fishing trips, we fish for the most common Chesapeake Bay fish species which also happen to be the best in the frying pan and oven too. The best fishing begins in early April and striper season begins at or near April 17th. The water is just too cold for many other species this time of year. The general fishing season lasts from April until November. The Chesapeake Bay is known for some of the best bottom fishing in the country with a wide variety of fish to fish for by anglers of all ages and fishing desires.


To reserve a Chesapeake Bay fishing Charter, Click Here.

Chesapeake Bay Sportfishing Charters

Chesapeake Bay Trophy Sport Striped Bass Fishing

Striped Bass Rockfish fishing

Striped Bass Rockfish

Striped bass, also known as rockfish or stripers, is the official fish of the State of Maryland and is considered by many to be the premier sport and commercial species on the Bay. There is nothing more exciting than having two or more "stripers" rockfish or striped bass hooked up all at the same time on one fishing trip.

Other Types of Fish we fish for in the Chesapeake Bay

  • Bluefish Fishing
  • Spot Fishing
  • Perch Fishing
  • Drum Fishing
  • Spanish Mackerel Fishing
  • and more

Types of Chesapeake Bay fishing we do are:

  • Trolling
  • Bottom fishing
  • Live Lining

Ocean Fishing

For you ocean fisherman anglers, Captain Mack and the Obsession will charter to go fishing for Marlin, Sailfish, Blue Fin Tuna and more.

Types of Ocean fishing we do:

  • Trolling
  • Bottom fishing
  • Chunking
  • Wreck fishing
Chesapeake Bluefish fishing

Chesapeake Bluefish

Chesapeake White Perch fishing

Chesapeake White Perch

Chesapeake Black Drum

Chesapeake Black Drum

Chesapeake spanish mackerel

Chesapeake Spanish Mackerel

Atlantic Ocean Sailfish

Atlantic Ocean Sailfish

Atlantic bluefin tuna

Atlantic Bluefin Tuna

Atlantic Ocean Blue Marlin

Atlantic Ocean Blue Marlin

Sport Fishing Rates

Chesapeake Bay Rates:

6 hour trip - $750.00
6 people.
Plus $90.00 for each person over 6 up to 27 passengers
6am till 12pm or 1pm till 7pm

8 hour trip - $950.00
6 people.
Plus $90.00 for each person over 6 up to 27 passengers
7am till 3pm

Ocean City Rates:

12 hour offshore Tuna/Marlin trip - $2,200.00
6 people.
Plus $90.00 for each person over 6 up to 27 passengers
7am till 7pm

To Make a $200 deposit for your Cheaspeake Bay Fishing Trip,
Please click the button below.

To Make a $400 deposit for your
Ocean Fishing Trip,
Please click the button below.

Things to bring on your Chesapeake Bay Fishing Charter:

  • Food & drinks for your fishing trip
  • No Bananas
  • NO glass bottles
  • NO liquor
  • Beer is OK
  • Soft soled shoes
  • Sunscreen
  • Camera
  • Hat & Sunglasses
  • Rain gear (as needed)
  • Warm clothes (as needed)