Four Winds Chartering 

4.8/5 (216 reviews)
 368 Dandy Haven Road, Hampton, VA 23664, United States

Four Winds Chartering 

4.8/5 (216)
 Angler's Choice
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368 Dandy Haven Road
Hampton, VA, United States

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.

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Customer reviews

Rating summary

4.8/5
out of 5 stars from 216 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.8/5

Photos & videos by reviewers (270)

Great Crew
Great Crew
Great Crew
+267

Angler rating

201
8
6
0
1

Anglers claimed

Good experience

93%

Appropriate for children

98%

Friendly captain

98%

Satisfied with the boat

99%

Recommend this charter

94%

Caught fish

85%

Showing 1 - 5 of 216 reviews
Showing: 5 of 216 reviews
Dustin Bivins
Dustin Bivins
5.0
Verified
Captain John and Tim
Half Day Trip (AM) on June 20, 20253 adults1 child
Captain John and Tim took great care of us today on a last minute inshore charter. Boat was spacious and well taken care of. Tim made sure everyone had turns reeling in fish and John was awesome making sure my daughter was as comfortable as possible while feeling a bit green. She was able to rally and finish the trip in great spirits. This team showed a great amount of professionalism and excitement even in relatively tough conditions. Everyone had a great time and the only complaint was that we didn’t book a full day. My bad. I’ll definitely book with these guys again. Thanks guys!
Review media 0
Review media 1
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Reported catch:
Spanish Mackerel
Response from Captain
June 21, 2025
👍👍👍👍👍 five thumbs up to your daughter little dicey there for a little while but pulled through great I was hoping we could get more at the island but the weather man had messed that forecast by a few feet awesome family we look forward to seeing you guys again soon
0
Cassidy Smart
Cassidy Smart
5.0
Verified
Great family trip
Half Day Trip (AM) on June 22, 20255 adults6 children
Four Winds Charter was perfect for our big family. They were so family oriented and laid back which is just what we need with 7 kids under the age of 13 coming on the trip! We booked a 4 hour charter and caught so many croakers. The captain handled the younger kids so well. Right off the bat we saw dolphins and capt John picked up the 5 year old to set him up on his seat to have a better view. The mates on the boat worked hard and kept everyone set up the whole time. Would definitely recommend this crew!
Review media 0
Response from Captain
June 22, 2025
Awesome family thanks for coming out today 🤗 and thanks for choosing us
0
Christine Greene
Christine Greene
5.0
Verified
Awesome Trip!
3 Hour Kids Trip (PM) on July 17, 20254 adults3 children
We had a great time with Captain John and Tim! We had 4 adults with 3 kids ages 9, 12 & 14 and had plenty of room and everyone caught something. We did some bottom fishing and trolling for some bigger fish. The crew was patient and flexible- bringing us out for a great 3 hour trip! We Highly recommend them for a fabulous family fishing trip! We'll be back for sure! Thanks Captain John! See you next time!
Reported catch:
Spanish Mackerel
Spotted Seatrout
1
Skye Brickhouse
Skye Brickhouse
5.0
Verified
All around great experience
2 Hour – Sunset and Fishing Cruise on June 21, 20258 adults
My family and I were pleasantly impressed with Captain John and Tim’s experience as we embarked on our scheduled trip. They kept us laughing and took care of us the whole way through. They had even sparked a greater interest in fishing for a few of us! They have our utmost respect and appreciation. Highly recommend them to fellow anglers!
Review media 0
1
Stephen Wright
Stephen Wright
5.0
Verified
Great trip
3/4 Day Trip on June 7, 20258 adults
It was a tough day on the water but definitely not the Captain or Crew's fault. We did catch some fish! Definitely had a new experience with targeting Cobia. Trolled for Spanish Mackerel and Blues as well. All in all the crew were knowledgeable the boat was clean, fast and comfortable. Thanks for a great time with family and friends.
Reported catch:
Bluefish
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
November 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
2 Hour – Sunset and Fishing Cruise
FREE Cancellation 14 days notice
2 Hour Trip, starts at 2:00 PM
Seasonal trip Aug 4 - Aug 4
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US $550 
Entire boat: up to 19 people
2 Hour – Sunset and Fishing Cruise
FREE Cancellation 14 days notice
2 Hour Trip, starts at 7:00 PM
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US $550 
Entire boat: up to 19 people
3 Hour Kids Trip (PM)
FREE Cancellation 14 days notice
3 Hour Trip, starts at 5:00 PM
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US $660 
Entire boat: up to 19 people
Half Day Trip (AM)
FREE Cancellation 14 days notice
4 Hour Trip, starts at 7:00 AM
Seasonal trip Apr 24 - Oct 31
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US $770 
Entire boat: up to 19 people
Half Day Trip (PM)
FREE Cancellation 14 days notice
4 Hour Trip, starts at 1:00 PM
Seasonal trip Apr 24 - Oct 31
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US $770 
Entire boat: up to 19 people
Half Day Trip (3PM)
FREE Cancellation 14 days notice
4 Hour Trip, starts at 3:00 PM
Seasonal trip Apr 24 - Oct 31
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US $770 
Entire boat: up to 19 people
3/4 Day Trip – Fall
FREE Cancellation 14 days notice
6 Hour Trip, starts at 6:30 AM
Seasonal trip Oct 31 - Dec 31
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US $990 
Entire boat: up to 19 people
3/4 Day Trip – Striper Trolling
FREE Cancellation 14 days notice
6 Hour Trip, starts at 6:30 AM
Seasonal trip Oct 31 - Dec 31
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US $990 
Entire boat: up to 19 people
3/4 Day Trip
FREE Cancellation 14 days notice
6 Hour Trip, starts at 7:00 AM
Seasonal trip Apr 24 - Oct 31
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US $990 
Entire boat: up to 19 people
Chesapeake Bay Shark Fishing (copy)
FREE Cancellation 14 days notice
4 Hour Trip, starts at 6:00 AM
Seasonal trip May 18 - Sep 30
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US $1,000 
Entire boat: up to 19 people
Chesapeake Bay Shark Fishing
FREE Cancellation 14 days notice
6 Hour Trip, starts at 6:00 AM
Seasonal trip May 18 - Sep 30
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US $1,200 
Entire boat: up to 19 people
Full Day Trip – Fall
FREE Cancellation 14 days notice
8 Hour Trip, starts at 6:30 AM
Seasonal trip Oct 31 - Dec 31
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US $1,400 
Entire boat: up to 19 people
Full Day Trip – Summer
FREE Cancellation 14 days notice
8 Hour Trip, starts at 7:00 AM
Seasonal trip May 1 - Sep 30 (Wed)
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US $1,440 
Entire boat: up to 19 people
There are 7 people looking at this charter.

Customer reviews

Rating summary

4.8/5
out of 5 stars from 216 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.8/5

Photos & videos by reviewers (270)

Great Crew
Great Crew
Great Crew
+267

Angler rating

201
8
6
0
1

Anglers claimed

Good experience

93%

Appropriate for children

98%

Friendly captain

98%

Satisfied with the boat

99%

Recommend this charter

94%

Caught fish

85%

Showing 1 - 5 of 216 reviews
Showing: 5 of 216 reviews
Dustin Bivins
Dustin Bivins
5.0
Verified
Captain John and Tim
Half Day Trip (AM) on June 20, 20253 adults1 child
Captain John and Tim took great care of us today on a last minute inshore charter. Boat was spacious and well taken care of. Tim made sure everyone had turns reeling in fish and John was awesome making sure my daughter was as comfortable as possible while feeling a bit green. She was able to rally and finish the trip in great spirits. This team showed a great amount of professionalism and excitement even in relatively tough conditions. Everyone had a great time and the only complaint was that we didn’t book a full day. My bad. I’ll definitely book with these guys again. Thanks guys!
Review media 0
Review media 1
Review media 2
Review media 3
Reported catch:
Spanish Mackerel
Response from Captain
June 21, 2025
👍👍👍👍👍 five thumbs up to your daughter little dicey there for a little while but pulled through great I was hoping we could get more at the island but the weather man had messed that forecast by a few feet awesome family we look forward to seeing you guys again soon
0
Cassidy Smart
Cassidy Smart
5.0
Verified
Great family trip
Half Day Trip (AM) on June 22, 20255 adults6 children
Four Winds Charter was perfect for our big family. They were so family oriented and laid back which is just what we need with 7 kids under the age of 13 coming on the trip! We booked a 4 hour charter and caught so many croakers. The captain handled the younger kids so well. Right off the bat we saw dolphins and capt John picked up the 5 year old to set him up on his seat to have a better view. The mates on the boat worked hard and kept everyone set up the whole time. Would definitely recommend this crew!
Review media 0
Response from Captain
June 22, 2025
Awesome family thanks for coming out today 🤗 and thanks for choosing us
0
Christine Greene
Christine Greene
5.0
Verified
Awesome Trip!
3 Hour Kids Trip (PM) on July 17, 20254 adults3 children
We had a great time with Captain John and Tim! We had 4 adults with 3 kids ages 9, 12 & 14 and had plenty of room and everyone caught something. We did some bottom fishing and trolling for some bigger fish. The crew was patient and flexible- bringing us out for a great 3 hour trip! We Highly recommend them for a fabulous family fishing trip! We'll be back for sure! Thanks Captain John! See you next time!
Reported catch:
Spanish Mackerel
Spotted Seatrout
1
Skye Brickhouse
Skye Brickhouse
5.0
Verified
All around great experience
2 Hour – Sunset and Fishing Cruise on June 21, 20258 adults
My family and I were pleasantly impressed with Captain John and Tim’s experience as we embarked on our scheduled trip. They kept us laughing and took care of us the whole way through. They had even sparked a greater interest in fishing for a few of us! They have our utmost respect and appreciation. Highly recommend them to fellow anglers!
Review media 0
1
Stephen Wright
Stephen Wright
5.0
Verified
Great trip
3/4 Day Trip on June 7, 20258 adults
It was a tough day on the water but definitely not the Captain or Crew's fault. We did catch some fish! Definitely had a new experience with targeting Cobia. Trolled for Spanish Mackerel and Blues as well. All in all the crew were knowledgeable the boat was clean, fast and comfortable. Thanks for a great time with family and friends.
Reported catch:
Bluefish
0

FAQs about Four Winds Chartering

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Cabin cruisers
Capacity
19 persons
Boat length
44 ft
Year built
1987
Restored in
2021
Boat manufacturer
Evans
Boat type
Downeast

Engine model
Cummins
Powered by
2 x 225HP
Max cruising speed
22 knots
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