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Meet The Winners: Charter Boat Captains

Meet The Winners: Charter Boat Captains


#1 Capt. Billy’s Fishing Charters

For over 30 years, Capt. Billy’s Fishing Charters has been making waves in the local recreational fishing industry.

Offering fishing trips, river cruises and ocean excursions, this family owned and operated charter business has the experience and the versatile fleet to accommodate any voyage.

The largest vessel, a 46-foot custom-made Markley Chesapeake Bay deadrise, Liquid Assets II, seats up to 35 passengers and can take passengers anywhere from the Chesapeake Bay to Rudee Inlet, Virginia Beach.

A 27-foot Albermarle, docked in Virginia Beach, is capable of taking passengers on near-shore trips in the ocean and seats six.

For those interested in exploring in-shore skinny waters, Capt. Billy’s fleet also includes a 20-foot Carolina Skiff which can fit up to three passengers.

Based between Smith Point and Windmill Point, at 545 Harveys Neck Road in Heathsville, these charters launch at the mouth of the Great Wicomico River from Ingram Bay Marina. The marina, also owned by Capt. Billy Pipkin and his family, offers rental cabins, small boat rentals, and features the Ship’s Store bait and tackle shop.

To reserve a charter, call 804-580-7292, or visit


#2 G&G Charters

Meet The Winners: Charter Boat CaptainsG&G Charters offers day-long fishing and evening expeditions on the Rappahannock River and the Chesapeake Bay.

A family owned business, Michael “Puddin” Glasco opened the charter company eight years ago with the help of his girlfriend and stepson. According to Capt. Puddin, he has been making his living on the water since he was eight years old.

G&G has two charter fishing boats, a 55-foot deadrise, Lucky Lady, which can seat up to 41 passengers, and a smaller 43-foot workboat-style deadrise, Karen Lynn, equipped to hold six passengers.

The company does not have a storefront, but books appointments over the phone or online and meets customers at the marinas where their boats are held. The Karen Lynn is docked at Chesapeake Cove Marina and the Lucky Lady at Norview Marina, both in Deltaville.

To reserve a trip with G&G Charters, call 804-832-3847 or visit


Third Place Winners

Four local charter companies tied for third place! Contact information and locations are:

  • Midnight Sun Charters, Capt. Ryan Rogers, 252 Wicomico Point Road, Heathsville, 804-580-0245,
  • Bay Quest Charters, Capt. David Rowe, operating from Lewisetta Marina in Lottsburg, Horn Harbor Marina in Port Haywood and Fairport Marina in Reedville. 804-529-6725,
  • Crabbe’s Charter Fishing, Capt. Danny Crabbe, 51 Railway Drive, Heathsville, 804-761-0908,
  • Sharlotte D. Charters, Capt. Chris Deal, Chesapeake Cove Marina, Deltaville, 804-824-4208.