Four Winds Chartering 

4.8/5 (241 reviews)
 368 Dandy Haven Road, Hampton, VA 23664, United States

Four Winds Chartering 

Hampton, VA, United States
44 ft
19
4.8/5 (241 reviews)

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.

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.

John O'Neal
Captain
John O'Neal
65 years of experience
ID & credentials verified
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
2 Hour – Sunset and Fishing Cruise
In high demand Last booked: 2 days ago
FREE Cancellation 30 days notice
2 hour trip starts at 7:00 PM
Cobia
Bluefish (Tailor)
Spanish Mackerel
Shark (Blacktip)
+8
US $550
Entire boat: up to 6 people
3 Hour Kids Trip (PM)
In high demand Last booked: 2 days ago
FREE Cancellation 30 days notice
3 hour trip starts at 5:00 PM
Cobia
Bluefish (Tailor)
Black Drum
Spanish Mackerel
+8
US $660
Entire boat: up to 6 people
Half Day Trip
In high demand Last booked: 1 day ago
FREE Cancellation 30 days notice
4 hour trip multiple starting times (7:00 AM, 1:00 PM, 3:00 PM, 5:00 PM)
Seasonal trip
Apr 24 - Oct 31
Cobia
Bluefish (Tailor)
Spanish Mackerel
Shark (Blacktip)
+8
US $770
Entire boat: up to 6 people
3/4 Day Trip – Fall
FREE Cancellation 30 days notice
6 hour trip starts at 6:30 AM
Seasonal trip
Oct 31 - Dec 31
Bass (Striped)
Tautog
US $990
Entire boat: up to 6 people
3/4 Day Trip – Striper Trolling
FREE Cancellation 30 days notice
6 hour trip starts at 6:30 AM
Seasonal trip
Oct 31 - Dec 31
Bass (Striped)
Bluefish (Tailor)
Tautog
US $990
Entire boat: up to 6 people
Chesapeake Bay Shark Fishing (copy)
FREE Cancellation 30 days notice
4 hour trip starts at 6:00 AM
Seasonal trip
May 18 - Sep 30
Cobia
Bluefish (Tailor)
Spanish Mackerel
Shark (Blacktip)
+3
US $1,000
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 30 days notice
6 hour trip starts at 7:00 AM
Seasonal trip
Apr 24 - Oct 31
Cobia
Bluefish (Tailor)
Black Drum
Spanish Mackerel
+7
US $1,100
Entire boat: up to 6 people
Chesapeake Bay Shark Fishing
FREE Cancellation 30 days notice
6 hour trip multiple starting times (6:00 AM, 8:00 AM)
Seasonal trip
May 18 - Sep 30
Dogfish
Shark (Sandbar)
Shark (Atlantic Sharpnose)
US $1,200
Entire boat: up to 6 people
Full Day Trip – Fall
FREE Cancellation 30 days notice
8 hour trip starts at 6:30 AM
Seasonal trip
Oct 31 - Dec 31
Bass (Striped)
US $1,400
Entire boat: up to 6 people
Full Day Trip – Summer
FREE Cancellation 30 days notice
8 hour trip starts at 7:00 AM
Seasonal trip
May 1 - Sep 30 (Wed)
Cobia
Spanish Mackerel
Flounder
Sheepshead
+8
US $1,440
Entire boat: up to 6 people
There are 24 people looking at this charter.

Customer reviews

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Rating

4.8
241 reviews
4.9
Boat & equipment
4.9
Captain & crew
4.8
Fishing Experience

Anglers' gallery (313)

What anglers say

92%
Great experience
98%
Family friendly
98%
Friendly captain
99%
Good boat
95%
Recommended
87%
Caught fish

All reviews (241)

Frequently mentioned
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Showing 15 of 241 reviews
Sarah Penrod
Sarah Penrod
us
Ohio, US
Member since 2026
5.0
Verified
New
We want to do this again!
3 Hour Kids Trip (PM) on July 14, 20263 adults3 children

We took the 3 hour Kids fishing cruise with Captain John. This was our first time doing a fishing charter and we don’t have much experience fishing. We all had a lot of fun and lost count of all the fish we pulled in (most too small to keep but we came home with a gallon size bag of fillets still). Captain John and the first mate Rylan were very laid back, helpful, and had everything we needed - we practically just had to reel the fish in. For the kids charters Captain John said he prioritizes quantity vs size of the fish and we got lucky and the fish were hungry. All of our kids want to do it again and the adults had a great time too. We appreciated that the boat had a toilet and plenty of shaded area too. Bring a cooler and some snacks and get ready for a great time.

Reported catch:
Atlantic Croaker
Lisa Regan
Lisa Regan
us
Virginia, US
Member since 2026
5.0
Verified
New
Great Fishing!
Half Day Trip on June 29, 20263 adults

Since it was rough out we were trolling on the Chesapeake. Captain John kept us in the Spanish mackerel so that all three of us always had a fish on the line. Mate Riley was awesome, keeping the lines clear and getting them back in the water. Captain and mate were friendly, engaging and answered all our fishing questions. We look forward to our next trip out with Four Winds Chartering!

Reported catch:
Spanish Mackerel
John O'Neal
Response from Captain

awesome review thanks we look forward to seeing you guys again soon

Stephanie Micheau
Stephanie Micheau
Repeat angler
us
Wisconsin, US
Member since 2024
2 trips
5.0
Verified
New
Fishing with John
Half Day Trip - 1:00 PM on June 26, 20263 adults

we had a great time on the boat. It was a beautiful day, the captain and 1st mate were great and informative. Showed us some pretty cool sites to and from the Bay. The only fish we caugh were Croakers so, i wish we had more of a variey..but, thats why they call it fishing..Right 😃 Regardless...it was a beautiful day on the boat and we had a great time!

Dalton Jevnick
Dalton Jevnick
us
Pennsylvania, US
Member since 2026
5.0
Verified
New
Fishing with John
Half Day Trip on June 30, 20263 adults

Captain John and his mates definitely have the customer experience in mind. It was very easy and convenient to book the trip. They are great with kids and inexperienced anglers. They cater to everyone of all skill sets. Highly recommended. I will be back. Dalton

Reported catch:
Spanish Mackerel
John O'Neal
Response from Captain

thank you we enjoyed you guys stay safe up on the iron

Justin Garcia
Justin Garcia
us
New Mexico, US
Member since 2026
5.0
Verified
New
Great time had by all!
Half Day Trip - 1:00 PM on June 17, 20265 adults

Captain John and Savannah made this a memorable time. Both made sure all enjoyed the trip. My mom who hates fishing, said she had fun, after catching a fish. An afternoon of fun! We are already looking forward to another character with the Four Winds crew!

John O'Neal
Response from Captain

thanks for the great review

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 $660 per group, additional US $66 per person after 6 guests - 3 Hour Kids Trip (PM) (3 hours)
  • US $770 per group, additional US $77 per person after 6 guests - Half Day Trip (4 hours)
  • US $770 per group, additional US $77 per person after 6 guests - Half Day Trip - 1:00 PM (4 hours)
  • US $770 per group, additional US $77 per person after 6 guests - Half Day Trip - 3:00 PM (4 hours)
  • US $770 per group, additional US $77 per person after 6 guests - Half Day Trip - 5:00 PM (4 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 $1,000 per group, additional US $110 per person after 6 guests - Chesapeake Bay Shark Fishing (copy) (4 hours)
  • US $1,100 per group, additional US $110 per person after 6 guests - 3/4 Day Trip (6 hours)
  • US $1,200 per group, additional US $150 per person after 6 guests - Chesapeake Bay Shark Fishing (6 hours)
  • US $1,200 per group, additional US $150 per person after 6 guests - Chesapeake Bay Shark Fishing - 8:00 AM (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)
When you book a trip with Four Winds Chartering, you can expect the following amenities onboard:
  • Toilet We have a full bathroom with mirror
  • GPS
  • Fishfinder
  • Flybridge
  • Live bait well
  • Refrigerator
  • Ice box
  • Radar
Trips booked with Four Winds Chartering include:
  • Rods, reels & tackle
  • Live bait (Sometimes we catch the live bait while out sometimes we use frozen and sometimes we just buy the bait before )
  • 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 (Fishing license is included and covers all guest )
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 (Tailor)
  • Cobia
  • Dogfish
  • Flounder
  • Shark (Blacktip)
  • Sheepshead
  • Spanish Mackerel
  • Speckled Trout
  • Triggerfish (Gray)
  • Weakfish

Your captain

John O'Neal
John O'Neal
John O'Neal

Hampton, Virginia, United States

12 Fishing Reports
ID & license verified
241 Customer reviews
Typical response 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.

Our Team
John O.

John O.

Captain

12 Fishing Reports
ID & license verified
241 Customer reviews
Typical response 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.

Our Team
John O.

John O.

Captain

The fish you can target

Striped Bass
Striped Bass
Black Drum
Black Drum
Bluefish (Tailor)
Bluefish (Tailor)
Cobia
Cobia
Dogfish
Dogfish
Flounder
Flounder
Blacktip Shark
Blacktip Shark
Sheepshead
Sheepshead
Spanish Mackerel
Spanish Mackerel
Speckled Trout
Speckled Trout
Gray Triggerfish
Gray Triggerfish
Weakfish
Weakfish
Striped Bass
Striped Bass
Black Drum
Black Drum
Bluefish (Tailor)
Bluefish (Tailor)
Cobia
Cobia
Dogfish
Dogfish

What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
19 persons
Boat length
44 ft
Year built
1987
Restored in
2024
Boat manufacturer
Evans
Boat type
Downeast
Engine model
Cummins
Powered by
2 x 225HP
Max cruising speed
22 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Reef Fishing
Wreck Fishing
Flats Fishing

Which fishing techniques you can try

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

Which amenities are available onboard

Toilet
We have a full bathroom with mirror
GPS
Fishfinder
Flybridge
Live bait well
Refrigerator
Ice box
Radar

What’s included in the trip price

Rods, reels & tackle
Live bait
Sometimes we catch the live bait while out sometimes we use frozen and sometimes we just buy the bait before
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
Fishing license is included and covers all guest

How cancellations work

Free cancellation up to 30 days prior to trip

You can cancel or modify your booking up to 30 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

What the listing policies are

Pickup not included

Transfer to/from departure site is not included in trip rates.

Child friendly
Kids our the future please bring them along ?
You keep catch
Catch and release allowed
Disabled accessible
we will do our best to get you on the boat

How you can pay

Pay online in full

Pay online in full through FishingBooker and save on credit card fees at the dock.

No additional fees.

Book with 30% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 30% 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.

What’s biting in Hampton right now

Bass (Striped)Bass (Striped)
Black DrumBlack Drum
Bluefish (Tailor)Bluefish (Tailor)
CobiaCobia
FlounderFlounder
SheepsheadSheepshead
Spanish MackerelSpanish Mackerel
Speckled TroutSpeckled Trout
WeakfishWeakfish

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