Boats & Captains

With 30 years of fishing experience under his belt and three boats later, Captain Drew was determined to create the ultimate chartering vessel. Big Worm made its first debut in the spring of 2017. Big Worm is a 52' long custom Chesapeake Bay Deadrise built by Millenium Marine equipped with a 900 HP Scania Turbo Diesel Engine. The boat is insured, equipped with extensive safety features and certified by the United States Coast Guard to carry 49 passengers. From corporate team building events to bachelor parties to family reunions, Captain Drew can cater to any occasion. Big Worm is rigged with top of the line tackle and ready to provide you and your party the best fishing experience the Chesapeake Bay has to offer. Reserve your date today!

We proudly serve customers from the Washington Metropolitan Area including but not limited to Annapolis, Kent Island, Rock Hall, Easton, Chesapeake Beach, Prince Frederick, Baltimore, Potomac, Silver Spring, Chevy Chase, McLean, Alexandria, Arlington, Reston, Manassas, Virginia Beach, Pennsylvania and West Virginia.

Come join Captain Bobby Rhodes aboard the Bonnie Sue for a day of Chesapeake Bay charter fishing excitement. Fishing out of Happy Harbor in Deale (MD) less than an hour's drive from Washington DC, we are close to some of the best fishing that the Chesapeake has to offer. Whether trolling for trophy rockfish in the spring, chasing bottom dwellers in the summer, or catching smaller rockfish during other times of the season, we're here to make sure that you and your friends and business colleagues have a great time.

Carrying up to 19 passengers, the Bonnie Sue features the newest in electronics and fishing tackle. So give us a call to arrange a day of sportfishing, cruising (bachelor parties, dinner cruises, etc.) on the magnificent Chesapeake Bay.

Come enjoy fishing or cruising to a nearby rest​urant with Captain Daniel Morrison aboard the "CHUBBY CHASER II". Captain Dan has spent his hole life on the Chesapeake Bay. Trolling, chumming, jigging, or bottom fishing Captain Dan will "get you on the meat". Fishing season starts mid-April when the trophy rockfish leave their spawning rivers and travel on out through the bay to the ocean.  In late fall some of those big fish return to the bay, and at that time the boat may move to Point Lookout. So give us a call to reserve your day out on the Chesapeake Bay.

Ebb Tide Charters offers spring trophy rockfishing trips on the Chesapeake Bay from the Happy Harbor Inn in Deale Maryland from mid April thru December. Ebb Tide is a 40' Evans with State of the art electronics, tackle & safety equipment. We can take up to 15 anglers.

Fin Hunter Charters offers charter fishing on Maryland's Chesapeake Bay. Captain Tim is a fully licensed and insured fishing guide. Fin Hunter is a 32' Judge Chesapeake with all the necessary marine electronics, fishing and safety gear.

Hallock's Grace Charters is a family owned and operated business. Trips depart from their private location in Deale, Maryland where you can bring your family aboard for a hands-on fishing or crabbing experience. Join their captain and crew anytime from April through November. You will fish aboard a 42' Provincial powered by a 450 HP Diesel engine, fitted with top of the line gear. There's room for six passengers on board and children of all ages are welcome. At the helm is Captain Thomas Hallock, a fifth-generation local fisherman who knows these waters well. He will help you spend your time on Chesapeake Bay fishing for Striped Bass, Bluefish, White Perch, Spanish Mackerel, and more. Captain Tom specializes in fishing with light tackle. He will help you land your catch using the most effective method, whether it's jigging, trolling, or drift fishing. You are welcome to keep your catch and he will clean and fillet it for you. Crab season starts in June, when you are welcome aboard to fish for this delicacy or to enjoy a crab feast on board with your family and friends.

April marks the beginning of the Chesapeake Bay Spring Trophy Rockfish season. Generally speaking the biggest of the biggest fish should be around our area until mid May. Book early to ensure your chance at a lifetime Trophy Rock Fish!

Summer means fishing for Rockfish, Bluefish, Flounder, Spanish Mackerel, Spot and Croaker! Most begin to arrive in our area in mid June and become more plentiful as the summer progresses. Come try a day of summertime fishing with us! Bring the kids for a great family day!

The cooler months of Fall offer the most diversified fishing of the year. Mixed catches of Rockfish, Blues, Flounder are common in September and October. Late October and November typically offer good Rockfish (Striped Bass) fishing.

The Last Hurrah is owned and operated by U.S.C.G. Master Captain Scott Singleton and runs fishing charters for up to 6 passengers. The 35-foot custom-built Markley, known simply as the "Hurrah" in fishing circles, is a safe, clean, well-maintained fishing machine! The boat and crew are female-friendly and we specialize in family outings. Need to book a corporate trip with a large party? No problem! Captain Scott can book multiple boats from the fleet to accommodate your company's needs. We chase fish in the Chesapeake Bay from April to December and use everything from trolling gear to fly-rods to catch 'em. Give Captain Scott a call or email today to book a day of Chesapeake Bay memories.

Safe, affordable, family fun!

The "Loosen Up" is a 48' Carman built in 1998 and is equipped with all the latest and best in fishing tackle. Enjoy Chesapeake Bay Fishing Aboard the Loosen Up: Whale Watching in Virginia Beach Over 30 years of Experience, 800 HP Engine and 96 Mile Radar Licensed for up to 44 passengers Fully equipped with all Coast Guard life saving equipment and more.

Two ship-to-shore radios, telephone, LORAN, color video fish finder, EPIRB

Chesapeake Bay Charter Fishing with Captain Tawn aboard the USCG-certified 22 passenger "Lucky Strike" for striped bass, seasonal rock fishing, light tackle chumming for stripers, bluefish, spot, perch, croaker, flounder, and trout fishing out of Happy Harbor Marina located in Deale, Maryland.

Spend a day fishing with Captain Trey Plumb. With over 30 years on the Chesapeake Bay, it's bound to be a good time! We offer Crabbing & Fishing Charters aboard our 32' custom deadrise fishing and crabbing boat. We can give you the full Chesapeake experience with custom tailored charters to give you a taste of everything the Chesapeake has to offer. Call us today and let us plan a Chesapeake Experience tailored just for you!

With Miss Ashleigh Charters, you can enjoy Chesapeake Bay fishing for striped bass. We specialize in fishing for the biggest stripers in the Chesapeake Bay. Looking for other species? Let’s fish for Spanish mackerel and bluefish, and do some Chesapeake Bay bottom fishing for hardhead, spot, and perch.

Maryland Chesapeake Bay Private Charter Boat fishing for Chesapeake Bay Striped Bass/Rockfish, Bluefish, Spanish Mackerel, Drum, Trout, Flounder, Croakers, Spot, Whiting & White Perch. Running 7 days a week.

Daily Chesapeake Bay Private Fishing and Cruising charters, centrally located in Deale and Annapolis MD locations. Easy Drive from Washington DC, Virginia, Pennsylvania, Baltimore & the Eastern Shore.

Relax and Enjoy the Chesapeake Bay!

Obse$$ion 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.

Patent Pending is one of the newest and most comfortable charter boats on the Bay. Built in 2010 by master boat builder, Jay Alan, the 46 ft. Markley-Alan is Coast Guard inspected for six passengers and has all of the newest navigational safety equipment.

Captain Ken Jeffries has been running Chesapeake Bay fishing charters for over 20 years.

Sellfish Charters offers first-class fishing charters throughout the Chesapeake Bay area. Whether you are an expert, a beginner or first-time fishermen, Captain Ken can show you around the Chesapeake Bay and ensure you have a great time catching your own fish and Maryland Blue Crabs.

You will fish aboard a 42 foot Evans commercial boat, originally built in 1999, and restored in 2014. The boat is powered by a 450 HP Caterpillar Diesel engine and has a capacity for 22 guests. It has all the electronics and safety features you need in order to have a productive and safe trip. There is an enclosed toilet on board which is a huge plus when you take out the whole family, and a multimedia system if you need extra entertainment. You’ll also have a live well for the bait, an icebox for the catch, and air-conditioning to provide some cooling in the Maryland heat.

Sellfish Charters will take you fishing in the inshore waters of the Chesapeake Bay in search of Striped Bass, Bluefish, Croaker, Black Drum, Flounder, White Perch, Crab, Speckled Trout and other species.

We offer a unique fishing experience aboard Sporting Wood. We are conveniently located in picturesque Deale, Maryland, which is located 25 minutes south of Annapolis and a short 45 minute drive from Washington D.C. and Baltimore. Full or half-day fishing excursions are available throughout the year. Dependent upon the season, we offer a full range of fishing techniques to include trolling, bottom fishing, chumming, and live bait. Our experienced crew provides full services and assistance including all fishing licenses, top of the line rods and reels, lures, and bait. Fish cleaning is available at the dock. Dinner cruises are also available. Sporting Wood is superbly maintained, meticulously clean and safe for all ages. Call to reserve and we will provide a day full of fun, excitement and fishing.

The Natural is a 47' Custom that hosts tournament level tackle and necessary equipment for both inshore and off shore charters. Powered by twin 540HP Cummins it has a cruise speed of 25kts to get you there quick. The Natural runs out of the Happy Harbor in Deale MD for spring and fall for rockfish; and Sunset Marina June through October for Shark, Tuna, Marlin, Wahoo, and dolphin.

The Natural is equipped with HDMI TV, Sirius/XM satellite radio, microwave, grill, and 2 A/C systems to make for a comfortable day or overnight on the water.

Join Captain Mike Garret aboard the Valerie Ann for a day of fun and excitement on the Chesapeake Bay. Offering half and full day charters for up to six passengers, Mike can put you on the fish, from trolling for trophy rockfish in the Spring to chasing Spanish Mackerel during hot weather. Fishing out of Rockhold Creek in Deale (MD), we're close to some of the best fishing opportunities the mid-Chesapeake has to offer. So give us a call soon to reserve your trip!

Captain Bobby runs a 38 foot Evans Somerset all Fiberglass Baybuilt with twin diesel and full electronics out of Deale MD from Paradise Marina.

Whether you are planning a Chesapeake Bay Striper Fishing trip, a Dinner Cruise around Annapolis, or an afternoon cruise to St. Michaels, the Wild Goose with Captain Jesse will make it a day to remember.