Chesapeake Bay Fishing Charters
Four Winds Chartering has a proud history on the waters of coastal Virginia, beginning in Virginia Beach in 1961. Today, based in Hampton, Virginia, we run private Chesapeake Bay trips with Captain John (25+ years on these waters). From family-friendly fishing charters to peaceful sunset cruises and respectful ashes-at-sea services, every trip is safe, personal, and memorable. We fish for Fall Stripers, Cobia, Croaker, Spot, Flounder, Bluefish, Sea Trout, Sea Mullet, Oyster Toad, Sand Shark, and more.
If you’re looking for first-class Chesapeake Bay fishing charters, you have come to the right place. Four Winds Chartering provides some of the best Chesapeake Bay fishing charters and Hampton fishing trips in Virginia. With more than six decades of chartering heritage, we’ve built our reputation around local knowledge, experience, and a passion for being on the water.
Four Winds Chartering is located in one of the finest sportfishing destinations on the East Coast and is based out of Hampton, VA. We also offer Chesapeake Bay sunset cruises if you’re looking for a relaxing way to end the day. We can take your group out for a cruise as the sun drops below the horizon, and you may even spot some wildlife along the way.
Established in 1961
Chesapeake Bay Fishing Charters, Shark Fishing & Sunset Cruises
Fishing Charters
Our Chesapeake Bay Charter Fishing Service offers amazing fishing trips out of Dandy Haven Marina. We target Flounder, Spot, Croaker, Black Drum, Striped Bass, Cobia, Bluefish, Spanish Mackerel, and Sea Trout species. All gear, bait, and licenses are included.
Sunset Cruise
When you book a Chesapeake Bay Sunset Cruise, the boat is exclusively yours. Enjoy a private evening as the sun drops over historic Hampton and the Chesapeake horizon. Spot dolphins, ospreys, and landmarks on this relaxing, unforgettable private cruise.
Burial at Sea
At Four Winds, we offer private and respectful ashes-at-sea services on the Chesapeake Bay. Whether honoring a fisherman, sailor, veteran, or loved one who simply cherished the water, this serene experience provides a meaningful and peaceful farewell.
Boat Support Services
Four Winds provides dependable and efficient marine support, including bridge inspections, dive operations, towing, line handling, pilot transfers, and construction assistance. We also help with marine surveys, security patrols, and private family outings on the water.
We target Fall Stripers, Cobia, Croaker, Spot, Flounder, Bluefish, Sea Trout, Sea Mullet, Oyster Toad, Sand Shark, and more!
We offer several affordable Chesapeake Bay fishing charter options. 4 hour Chesapeake Bay Fishing Trips, 6 hour Chesapeake Bay Fishing Charters and 8 hour Chesapeake Bay Sportfishing Adventures. We offer bottom fishing for Flounder, Spot, Black Drum and Croaker. On our Chesapeake Bay trolling fishing charters we fish for Rockfish, Cobia, Sea Trout, Bluefish Spanish Mackerel and More!
In the Fall we offer exciting Chesapeake Bay Striper Fishing Charters. Striper provide fast action when they take your bait for the ride of its life. Striped Bass fishing is one of our favorites and will soon be one of yours! Captain John knows all of the best fishing spots to catch Striped Bass in the Chesapeake Bay waterways and Hampton, Virginia. We can’t guarantee all catches will be a record fish, but we will get you hooked up with some beauties and will give you a fighting chance at finding the catch of a lifetime. Please contact John today to book your next fishing charter on the World-Famous Chesapeake Bay.
Sportfishing is the perfect way to entertain church groups, clients, family, and friends while visiting Chesapeake Bay and the Hampton, Virginia area. Captain John has spent years fishing these local waters and works hard to ensure every guest enjoys an unforgettable day on the water. Whether you’re an experienced angler or a first-timer, Four Winds Chartering offers Hampton fishing charters you’ll be excited to share with friends and family.
Call now 757-713-2275









