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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Rating

4.8
216 reviews
5
201
4
8
3
6
2
0
1
1
4.9
Boat & equipment
4.9
Captain & crew
4.8
Fishing Experience

Anglers' gallery (270)

Great Crew
Great Crew
Great Crew
Great Crew
Great Crew
great boat and crew. Capt John and first mate Tim are both excellent
+264

What anglers say

93%
Great experience
98%
Family friendly
98%
Friendly captain
99%
Good boat
94%
Recommended
85%
Caught fish

All reviews (216)

Filter
Showing 15 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
Craig Mills
Craig Mills
5.0
Verified
Captain and First Mate
Half Day Trip (AM) on July 26, 202511 adults
We had a great time catching fish and learning how to reel in them in. A new experience for our crew. The Captain and First Mate was great in helping and teaching us. Takes patience to teach newbies how to fish in the open water. The waves got a bit tough at times, but that wasn't a pond we were in! Thanks!
Review media 0
Review media 0
Review media 0
Response from Captain
August 8, 2025
Thanks for the great review team work makes the dream work
1
Alton Wilder
Alton Wilder
5.0
Verified
Amazing Experience
2 Hour – Sunset and Fishing Cruise on September 20, 202510 adults
We booked a trip to celebrate my aunt's birthday. It was an amazing experience. Captain John and his mate made it an incredible event. Auntie loved it. That evening, she said it was her best birthday. I highly recommend, and I'll be back to take another trip with them in the future!
Response from Captain
September 22, 2025
awesome glad she enjoyed 75 is a major milestone we had a great time with you guys i just wish the clouds were gone so we could enjoy the beautiful sunset
0
Recoldemon Winn
Recoldemon Winn
5.0
Verified
Fishing on the Bay
Half Day Trip (PM) on September 5, 20257 adults
Our day of fish g on the bay was great !! Family day with my Dad uncles brothers and cousins was a very great and exploring memorable occasion’ captain john and first mate bat were very accommodating and extremely helpful in making the trip a great one
Review media 0
Reported catch:
Bluefish
Spanish Mackerel
Response from Captain
September 6, 2025
hey thanks for the great review we appreciate you and can’t wait to do it again
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
January 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
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 15 people looking at this charter.

Rating

4.8
216 reviews
5
201
4
8
3
6
2
0
1
1
4.9
Boat & equipment
4.9
Captain & crew
4.8
Fishing Experience

Anglers' gallery (270)

Great Crew
Great Crew
Great Crew
Great Crew
Great Crew
great boat and crew. Capt John and first mate Tim are both excellent
+264

What anglers say

93%
Great experience
98%
Family friendly
98%
Friendly captain
99%
Good boat
94%
Recommended
85%
Caught fish

All reviews (216)

Filter
Showing 15 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
Craig Mills
Craig Mills
5.0
Verified
Captain and First Mate
Half Day Trip (AM) on July 26, 202511 adults
We had a great time catching fish and learning how to reel in them in. A new experience for our crew. The Captain and First Mate was great in helping and teaching us. Takes patience to teach newbies how to fish in the open water. The waves got a bit tough at times, but that wasn't a pond we were in! Thanks!
Review media 0
Review media 0
Review media 0
Response from Captain
August 8, 2025
Thanks for the great review team work makes the dream work
1
Alton Wilder
Alton Wilder
5.0
Verified
Amazing Experience
2 Hour – Sunset and Fishing Cruise on September 20, 202510 adults
We booked a trip to celebrate my aunt's birthday. It was an amazing experience. Captain John and his mate made it an incredible event. Auntie loved it. That evening, she said it was her best birthday. I highly recommend, and I'll be back to take another trip with them in the future!
Response from Captain
September 22, 2025
awesome glad she enjoyed 75 is a major milestone we had a great time with you guys i just wish the clouds were gone so we could enjoy the beautiful sunset
0
Recoldemon Winn
Recoldemon Winn
5.0
Verified
Fishing on the Bay
Half Day Trip (PM) on September 5, 20257 adults
Our day of fish g on the bay was great !! Family day with my Dad uncles brothers and cousins was a very great and exploring memorable occasion’ captain john and first mate bat were very accommodating and extremely helpful in making the trip a great one
Review media 0
Reported catch:
Bluefish
Spanish Mackerel
Response from Captain
September 6, 2025
hey thanks for the great review we appreciate you and can’t wait to do it again
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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