Family fishing, Private Sunset Cruises, Ashes at Sea, and more!
Quit Wishing, Let’s Go Fishing
in world-famous Chesapeake Bay
Chesapeake Bay Fishing Charters based in Hampton, Virginia
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Chesapeake Bay Fishing Charters

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 the best Chesapeake Bay fishing charters and Hampton fishing trips in Virginia. Four Winds Chartering is located in the finest sportfishing location on the East Coast and is based out of Hampton, VA. We also offer Chesapeake Bay sunset cruises if you’re looking for an inspiring end cap to the end, we can take your group out for a cruise as the sun drops down below the horizon and you may even see some wildlife swimming about.

Welcome to Four Winds Chartering, based in beautiful Hampton, Virginia — the gateway to the world-famous Chesapeake Bay

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 757.713.2257
★ ★ ★ ★ ★

Wonderful experience! John and Tim are both excellent! We did the 4hr trip in the morning with the most perfect weather in mid-September. They handled everything – the fishing rods, the baits, helping you fish and reel it in and cleaning the catch however you wanted. Very friendly duo, felt very safe in their hands. Definitely will be a repeat customer and highly recommend!

Margarita Summer 2025
★ ★ ★ ★ ★

Had an awesome experience with Capt John and his Mate! A fun adventure out on the water where our whole crew enjoyed the good times and catching a few fish. Highly recommended!

Andrew Kilgore Fall 2025
★ ★ ★ ★ ★

Capt John and First Mate Tim are phenomenal! This trip was so fun and we learned a lot as well! If you’re looking for something to do and go, have fun or just to catch some fish and be out on the water, this is definitely the company you wanna use.

Suzanne Carter Summer 2025
★ ★ ★ ★ ★

This was hands down the best fishing trip I’ve ever been on. From start to finish, everything was smooth, fun, and unforgettable. The crew was knowledgeable and made sure we were comfortable the entire time. The equipment was top-notch, and we were taken to the perfect spots where the fish were biting nonstop. Everyone in our group had an amazing time, and the atmosphere was relaxed yet exciting. We caught more fish than we ever expected, and the memories made will last a lifetime. Highly recommend this trip.

Joey Carawan Fall 2025