Four Winds Chartering is a family-owned, locally operated fishing charter company based in Hampton, Virginia, the gateway to the world-famous Chesapeake Bay. Captain John has more than 25 years of experience on these waters, guiding private trips out of Dandy Haven Marina alongside First Mate Tim, offering everything from family-friendly fishing to peaceful sunset cruises and respectful ashes-at-sea ceremonies.

Trips target Fall Stripers, Cobia, Croaker, Spot, Flounder, Bluefish, Sea Trout, Sea Mullet, Oyster Toad, and Sand Shark, using bottom fishing for Flounder, Spot, Black Drum, and Croaker, or trolling for Rockfish, Cobia, Sea Trout, Bluefish, and Spanish Mackerel. Fall brings a particular specialty: exciting Striped Bass charters with fast, hard-fighting action once the Stripers take the bait. Charter lengths run 4, 6, or 8 hours, with all gear, bait, and fishing licenses included in every trip.

Beyond fishing, Four Winds offers a private Chesapeake Bay Sunset Cruise with the boat exclusively reserved for one group, taking in dolphins, ospreys, and historic Hampton landmarks along the way, plus a Tiki Boat Cruise option. The business also provides commercial boat support services, including bridge inspections, dive operations, towing, line handling, pilot transfers, marine surveys, security patrols, and construction assistance.

Guest reviews consistently praise Captain John and First Mate Tim for their friendly, knowledgeable, and safety-focused approach, with multiple reviewers specifically highlighting how smoothly everything was handled, from baiting hooks to cleaning the catch, and describing the trip as one of the best fishing experiences they’ve had.

For anglers and groups near Hampton looking for a fishing charter, sunset cruise, or ashes-at-sea service on the Chesapeake Bay, Four Winds Chartering offers a highly reviewed, 25-year veteran operation with Captain John out of Dandy Haven Marina.