Four Winds Chartering

Four Winds Chartering runs the most fun and exciting fishing adventures in the beautiful city of Hampton, Virginia. They make each trip enjoyable and a learning experience for their guests, by going straight to the best fishing spots and giving sound advice on how to catch and reel in the fish. This is what they will do with you!

You will fish aboard a 44’ Evans saltwater fishing boat, which is powered by two 225 HP Cummins engines. The boat is safe and reliable, being equipped with all the safety equipment and electronics you need for a successful trip. It has a flybridge and a toilet, which is an absolute must-have if you are taking kids out on the water.

These waters are brimming with life, so there’s a variety of fish species you can expect to come across. You will target Striped Bass, Spotted Seatrout, the super tasty Flounder, Triggerfish, Black Drum, and other exciting species that call these waters home.

The boat is owned by Captain John O’Neal who has been fishing these waters from an early age and is familiar with all the productive spots in the area. He will provide you with rods, reels, tackle, lures, and a fishing license, so all you have to bring is a positive attitude and sunglasses.

In the words of Captain John: “Quit wishing – let’s go fishing”! Join Four Winds Chartering and have some serious fun! Since 1961.



Select date to see available trips and rates:

  • Private trip
    2 Hour – Sunset and Fishing Cruise
    Low rate deposit non-refundable
    2 Hour Trip, starts at 6:30 PM
    US $550
    If you would just like to get out on the water and enjoy the views then this is the trip for you. 2 hours of site seeing and a little fishing around the Chesapeake Bay and Virginia Beach ocean front. Bring your booze and we will supply the fishing and tackle and sunset. The starting time may be earlier in the winter months or later in the summer season. Times maybe adjusted.
    Targeted fish
    Cobia
    Cobia
    Bluefish
    Bluefish
    Spanish Mackerel
    Spanish Mackerel
    Spotted Seatrout
    Spotted Seatrout
    Weakfish
    Weakfish
  • Private trip
    Half Day Trip (AM)
    Low rate deposit non-refundable
    4 Hour Trip, starts at 7:00 AM
    Seasonal trip Apr 24 - Oct 18
    US $770
    This is a morning trip with a capacity of 27 people. After six people there is an additional per person charge. This is a moring trip for those who want to get an early start on the water. This great short trip will see you targeting Spotted Seatrout, Flounder, Bluefish, Cobia, Fall Stripers, Croaker, Sea Mullet, Sand Shark, Blackfin Shark, Oyster Toad, Spanish Mackerel, and other species of the Chesapeake Bay.
  • Private trip
    Half Day Trip (PM)
    Low rate deposit non-refundable
    4 Hour Trip, starts at 1:00 PM
    Seasonal trip Apr 24 - Oct 18
    US $770
    This is an afternoon trip with a capacity of 27 people. After six people there is an additional per person charge. This great short trip will see you targeting Spotted Seatrout, Flounder, Bluefish, Cobia, Fall Stripers, Croaker, Sea Mullet, Sand Shark, Blackfin Shark, Oyster Toad, Spanish Mackerel, and other species of the Chesapeake Bay. Departure time may vary. Make sure to consult with the captain prior to the trip.
  • Private trip
    Half Day Trip (PM) (3PM)
    Low rate deposit non-refundable
    4 Hour Trip, starts at 3:00 PM
    Seasonal trip Apr 24 - Oct 18
    US $770
    This is an afternoon (3PM) trip with a capacity of 27 people. After six people there is an additional per person charge. This great short trip will see you targeting Spotted Seatrout, Flounder, Bluefish, Cobia, Fall Stripers, Croaker, Sea Mullet, Sand Shark, Blackfin Shark, Oyster Toad, Spanish Mackerel, and other species of the Chesapeake Bay. Departure time may vary. Make sure to consult with the captain prior to the trip.
  • Private trip
    3/4 Day Trip
    Low rate deposit non-refundable
    6 Hour Trip, starts at 7:00 AM
    Seasonal trip Apr 24 - Oct 18
    US $990
    This is a 6-hour trip with a capacity of 27 people. After six people there is an additional per person charge. Fish on the beautiful and productive waters of Chesapeake Bay for Croaker, Sand Shark, Blackfin Shark, Cobia, Spotted Seatrout, Fall Stripers, Flounder, Sea Mullet, Bluefish, Oyster Toad, Spanish Mackerel, and other species.
  • Private trip
    3/4 Day Trip – Fall
    Low rate deposit non-refundable
    6 Hour Trip, starts at 6:30 AM
    Seasonal trip Oct 31 - Dec 31
    US $990
    Join Captain John for 6 hours of trolling. This trip has a capacity of 27 people. After six people there is an additional per person charge. You will mostly target Stripers and Rockfish. This trip is seasonal, so make sure you book your spot on time. Your fishing equipment and bait are included. In case you need any help, the first mate will be there to assist you.
  • Private trip
    3/4 Day Trip – Striper Trolling
    Low rate deposit non-refundable
    6 Hour Trip, starts at 6:30 AM
    Seasonal trip Oct 31 - Dec 31
    US $990
    This trip is for Striper enthusiasts. A quick trip to local structures where the Stripers live will have your lines in the water in no time. This trip will consist of casting and jigging and trolling, so seasoned anglers are preferred. However, novices are encouraged to give it a try. This is a short duration trip of 6 hours, with the start time-varying as well. Bring your snacks, and drinks along too. The capacity of the boat is 13 people.
  • Private trip
    Full Day Trip – Fall
    Low rate deposit non-refundable
    8 Hour Trip, starts at 6:30 AM
    Seasonal trip Oct 31 - Dec 31
    US $1,400
    On this trip, Capt. John will take you out for 8 hours of trolling. The capacity of the boat is 19 people. After six people there is an additional per-person charge. Your main targets for the day will be Striper and Rockfish. Make sure to book your spot on time, as this trip is seasonal. Your fishing equipment and lures will be provided, feel free to bring any snacks and drinks you want.
    Targeted fish
    Bass (Striped)
    Striped Bass
  • Private trip
    Full Day Trip – Summer
    Low rate deposit non-refundable
    8 Hour Trip, starts at 7:00 AM
    Seasonal trip May 1 - Sep 30 (Wed)
    US $1,440
    This is a full-day trip for up to 19 people! After six people there is an additional per person charge. The trip will see you fishing the very productive fishing grounds of the Chesapeake Bay for Fall Stripers, Croaker, Spanish Mackerel, Cobia, Spotted Seatrout, Flounder, Bluefish, Sea Mullet, Sand Shark, Blackfin Shark, Oyster Toad, and other species.
  • Private trip
    Chesapeake Bay Shark Fishing
    Low rate deposit non-refundable
    8 Hour Trip, starts at 6:00 AM
    Seasonal trip May 18 - Sep 15
    US $1,500
    Shark fishing is one of the most fun adventures you can go. This trip will put you up against some of the fiercest predators of the seas. Sharks put up a fight no matter their size so you're sure to experience plenty of excitement reeling one in. The capacity of the boat is 27 people. After six people there is an additional per person charge.
There are 6 people looking at this charter.

FAQs about Four Winds Chartering

Four Winds Chartering offers the following trips to customers:
  • US $550 per group, additional US $55 per person after 6 guests - 2 Hour – Sunset and Fishing Cruise (2 hours)
  • US $770 per group, additional US $77 per person after 6 guests - Half Day Trip (AM) (4 hours)
  • US $770 per group, additional US $77 per person after 6 guests - Half Day Trip (PM) (4 hours)
  • US $770 per group, additional US $77 per person after 6 guests - Half Day Trip (PM) (3PM) (4 hours)
  • US $990 per group, additional US $99 per person after 6 guests - 3/4 Day Trip (6 hours)
  • US $990 per group, additional US $99 per person after 6 guests - 3/4 Day Trip – Fall (6 hours)
  • US $990 per group, additional US $125 per person after 6 guests - 3/4 Day Trip – Striper Trolling (6 hours)
  • US $1,400 per group, additional US $140 per person after 6 guests - Full Day Trip – Fall (8 hours)
  • US $1,440 per group, additional US $110 per person after 6 guests - Full Day Trip – Summer (8 hours)
  • US $1,500 per group, additional US $150 per person after 6 guests - Chesapeake Bay Shark Fishing (8 hours)

When you book a trip with Four Winds Chartering, you can expect the following amenities onboard:
  • Toilet
  • GPS
  • Fishfinder
  • Flybridge
  • Live Bait Well
  • Refrigerator
  • Ice Box
  • Radar

Trips booked with Four Winds Chartering include:
  • Rods, reels & tackle
  • Live Bait
  • Lures
  • Catch cleaning & filleting (Don't forget the mate work's for tips )
  • First Mate (Works for tips please don't forget to tip the mate)
  • Fishing License

Four Winds Chartering offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Reef Fishing
  • Wreck Fishing
  • Flats Fishing

Four Winds Chartering offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Drift Fishing
  • Deep Sea Fishing

Top targeted fish species with Four Winds Chartering include:
  • Bass (Striped)
  • Black Drum
  • Bluefish
  • Cobia
  • Flounder
  • Spanish Mackerel
  • Spotted Seatrout
  • Triggerfish (Gray)
  • Weakfish

Meet the Captain

John O'Neal
Hampton, Virginia, United States
4 Fishing Reports
147 Customer reviews
Response time within an hour
Member since December 2016
Angler's Choice
The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.
Captain John was born and raised in Hampton Roads where he learned to swim and fish in the Chesapeake Bay. He worked as an ironworker for many years, and finally was able to purchase the Four Winds boat. He did it to share his passion of fishing with others.

About this listing

Targeted species

Bass (Striped) Striped Bass
Black Drum Black Drum
Bluefish Bluefish
Cobia Cobia

Boat specs

Evans (Sportfishing) originally built in 1987, and restored in 2021. Powered by 2 225HP Cummins engines, with a maximum cruising speed of 22 knots.

Length
44 ft
Capacity
19 persons

Types of fishing

Inshore Fishing
Nearshore Fishing
Reef Fishing
Wreck Fishing
Flats Fishing

Fishing techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Drift Fishing
Deep Sea Fishing

Amenities

Toilet
GPS
Fishfinder
Flybridge
Live Bait Well
Refrigerator

Trip includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Don't forget the mate work's for tips
First Mate
Works for tips please don't forget to tip the mate
Fishing License

Cancellation policy

Deposit non-refundable

If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.

Listing policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed
Disabled Accessible
we will do our best to get you on the boat

Payment

Book with 10% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

Cash
Visa
Mastercard
American Express
PayPal
Bank Transfer
When paying the remaining balance with a credit card, an additional 4% charge will apply.

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