Chesapeake Bay Fly Fishing Charters (Virginia)

Experience world-class Chesapeake Bay fly fishing charters with Captain Denny, a lifelong outdoorsman and expert Virginia fly fishing guide. Our private trips focus on redfish, trout, and striped bass in the secluded backcountry waters of the Eastern Shore. From Cape Charles to Oyster, you’ll explore flats, tidal creeks, and hidden coves where other anglers rarely venture.

Using a custom 20' Sea Ark jet boat with a 115 HP Mercury engine, we access shallow waters safely and quietly, perfect for sightcasting and light tackle fishing. Trips range from 4- to 8-hour adventures, including 2-day experiences for dedicated anglers, and all trips are tailored to your skill level, whether you’re a first-timer or seasoned pro.

Captain Denny brings over 50 years of Virginia fishing experience, having run offshore trips in the 1990s and opened two tackle shops. He is a USCG-certified captain and pilot, ensuring safety and expert guidance on every trip. Guests can also learn fly casting techniques, fishing fundamentals, or simply enjoy the serenity of untouched wilderness.

Peak season runs from October through mid-December for clear-water sight fishing, but we also offer eco-style trips during shoulder seasons, showcasing the pristine backcountry with minimal fishing pressure. Each private charter combines expert instruction, local knowledge, and access to remote waters few anglers ever see, making every trip unforgettable.

Book your private fly fishing charter Chesapeake Bay today and enjoy a personalized, family-friendly adventure where the real reward is both the fishing and the incredible backcountry experience.