This Chesapeake Bay fishing charter is designed for newcomers who want a relaxed and productive day on the water. Whether you’re bringing the kids, trying fishing for the first time, or just want an easy-going experience, this trip offers calm inshore waters and steady bites. You’ll target Croaker, Spot, Flounder, and Spanish Mackerel using simple light tackle methods. Captain Jack and his first mate provide all the instruction, gear, and local knowledge needed, so you can focus on enjoying yourself. This is one of the best family-friendly Chesapeake Bay fishing trips, offering hands-on learning and plenty of smiles.

This private, half-day (4-hour) inshore fishing trip explores the productive, calm waters of Chesapeake Bay. Anglers will target a variety of species, including Redfish (Red Drum), Sea Trout, Croaker, Flounder, and Striped Bass. This excursion is suitable for all skill levels, from families with children to experienced anglers seeking a shorter outing. The guided trip covers fishing licenses, rods, reels, tackle, and bait. Guests should bring their own food and drinks. Focus is placed on utilizing the boat's proximity to shore for a relaxing, high-action fishing experience.

This private, full-day (8-hour) inshore fishing trip is Captain Jack's most popular offering in Chesapeake Bay. This extended duration provides ample time and flexibility to target a wide variety of migratory species, including Red Drum (Redfish) and Cobia, with options to switch to Spanish Mackerel or Spadefish based on conditions. The trip is ideal for all skill levels seeking maximum time on the water for high-action fishing. The charter includes an expert guide, fishing licenses, and all necessary quality gear, including rods, reels, tackle, and bait. Guests must bring their own food and drinks.

Designed for experienced anglers, this trip is all about strategy, technique, and serious hook-ups. Chase after Cobia, Red Drum, Striped Bass, and Sheepshead using a range of methods from bottom fishing and jigging to sight casting and trolling. You'll fish around structure, open water, and hot zones only known to local pros. This Chesapeake Bay sportfishing charter is perfect for guests who know their way around a rod and want to land something worthy of a photo—and maybe dinner. Ideal for individuals or groups who want a challenge, this is one of the top advanced Chesapeake Bay fishing charters in Virginia.

This private, full-day (6-hour) inshore fishing trip explores the productive, central waters of Chesapeake Bay. Anglers will target popular migratory species such as Cobia, Redfish (Red Drum), Spanish Mackerel, and Spadefish. This excursion offers an ideal balance of convenience and action, suitable for all skill levels. The guided trip is fully equipped, covering fishing licenses, top-tier rods, reels, tackle, and bait. Guests should plan to bring their personal food and drinks. This trip is designed to maximize time on the water, providing ample opportunity to hook quality fish.