Four Winds Chartering 

4.8/5 (197 reviews)
  Recent reports
 368 Dandy Haven Road, Hampton, VA 23664, United States–
4.8/5 (197 reviews)
• 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 197 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.8/5

Photos & videos by reviewers (229)

Fun time
Fun time
Fun time
+226

Angler rating

184
6
6
0
1

Anglers claimed

Good experience

94%

Appropriate for children

98%

Friendly captain

99%

Satisfied with the boat

99%

Recommend this charter

95%

Caught fish

84%

Showing 1 - 5 of 197 reviews
Showing: 5 of 197 reviews
Dustin B.
Dustin B.
5.0/5

Jun 20, 2025

Half Day Trip (AM)

Captain John and Tim

VERIFIED

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!

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...  

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Captain replied
 Dustin B. recommends Four Winds Chartering
 Dustin B. recommends Four Winds Chartering
undefined (The Captain)
Replied on 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

Christine G.
Christine G.
5.0/5

Jul 17, 2025

3 Hour Kids Trip (PM)

Awesome Trip!

VERIFIED
NEW

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!

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...  

 Christine G. recommends Four Winds Chartering
 Christine G. recommends Four Winds Chartering

Cassidy S.
Cassidy S.
5.0/5

Jun 22, 2025

Half Day Trip (AM)

Great family trip

VERIFIED

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!

Four Winds Charter was perfect for our big family. They were so family oriented and laid back which is just what we need with...  

Review media 0
Captain replied
 Cassidy S. recommends Four Winds Chartering
 Cassidy S. recommends Four Winds Chartering
undefined (The Captain)
Replied on June 22, 2025
Awesome family thanks for coming out today 🤗 and thanks for choosing us

LaTisha W.
LaTisha W.
5.0/5

May 16, 2025

2 Hour – Sunset and Fishing Cruise

Book your excursion today!

VERIFIED

I recently booked a fishing excursion with Four Winds Chartering for my husband’s birthday, and it was an unforgettable experience! The boat was well-equipped and spacious. The crew was extremely welcoming. My husband and his friends had such a fantastic time that they ended up extending their outing by paying for an extra hour on the water. If you’re looking for a fun day out, I highly recommend Four Winds Chartering!

I recently booked a fishing excursion with Four Winds Chartering for my husband’s birthday, and it was an unforgettable experience!...  

 LaTisha W. recommends Four Winds Chartering
 LaTisha W. recommends Four Winds Chartering

LARRY W.
LARRY W.
5.0/5

Jul 19, 2025

Half Day Trip (AM)

Generational Fun

VERIFIED
NEW

I took my sons and grandson on this trip. I told the captain that we wanted trophies AND dinner. Four Winds didn’t disappoint. We’re already planning next time. Great captain and crew. “Don’t miss it if you possibly can.”

I took my sons and grandson on this trip. I told the captain that we wanted trophies AND dinner. Four Winds didn’t disappoint....  

 LARRY W. recommends Four Winds Chartering
 LARRY W. recommends Four Winds Chartering

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
August 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
Loading...
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 9 people looking at this charter.

Customer reviews

Rating summary

4.8/5
out of 5 stars from 197 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.8/5

Photos & videos by reviewers (229)

Fun time
Fun time
Fun time
+226

Angler rating

184
6
6
0
1

Anglers claimed

Good experience

94%

Appropriate for children

98%

Friendly captain

99%

Satisfied with the boat

99%

Recommend this charter

95%

Caught fish

84%

Showing 1 - 5 of 197 reviews
Showing: 5 of 197 reviews
Dustin B.
Dustin B.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Captain John and Tim

VERIFIED

Half Day Trip (AM) on June 20, 2025

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!

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...  

Review media 0
Review media 1
Review media 2
Review media 3
 Dustin B. recommends Four Winds Chartering
undefined (The Captain)
Replied on 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

Christine G.
Christine G.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Awesome Trip!

VERIFIED
NEW

3 Hour Kids Trip (PM) on July 17, 2025

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!

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!  

 Christine G. recommends Four Winds Chartering

Cassidy S.
Cassidy S.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great family trip

VERIFIED

Half Day Trip (AM) on June 22, 2025

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!

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...  

Review media 0
 Cassidy S. recommends Four Winds Chartering
undefined (The Captain)
Replied on June 22, 2025
Awesome family thanks for coming out today 🤗 and thanks for choosing us

LaTisha W.
LaTisha W.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Book your excursion today!

VERIFIED

2 Hour – Sunset and Fishing Cruise on May 16, 2025

I recently booked a fishing excursion with Four Winds Chartering for my husband’s birthday, and it was an unforgettable experience! The boat was well-equipped and spacious. The crew was extremely welcoming. My husband and his friends had such a fantastic time that they ended up extending their outing by paying for an extra hour on the water. If you’re looking for a fun day out, I highly recommend Four Winds Chartering!

I recently booked a fishing excursion with Four Winds Chartering for my husband’s birthday, and it was an unforgettable experience! The boat was well-equipped and spacious. The crew was extremely welcoming. My husband and his friends had such a fantastic time that they ended up extending their outing by paying for an extra hour on the water. If you’re looking for a fun day out, I highly recommend Four Winds Chartering!  

 LaTisha W. recommends Four Winds Chartering

LARRY W.
LARRY W.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Generational Fun

VERIFIED
NEW

Half Day Trip (AM) on July 19, 2025

I took my sons and grandson on this trip. I told the captain that we wanted trophies AND dinner. Four Winds didn’t disappoint. We’re already planning next time. Great captain and crew. “Don’t miss it if you possibly can.”

I took my sons and grandson on this trip. I told the captain that we wanted trophies AND dinner. Four Winds didn’t disappoint. We’re already planning next time. Great captain and crew. “Don’t miss it if you possibly can.”  

 LARRY W. recommends Four Winds Chartering

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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What’s biting in Hampton right now

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Recent fishing reports


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