Four Winds Chartering 

4.8/5 (224 reviews)
 368 Dandy Haven Road, Hampton, VA 23664, United States

Four Winds Chartering 

4.8/5 (224)
 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.

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

Anglers' gallery (277)

What anglers say

93%
Great experience
98%
Family friendly
98%
Friendly captain
99%
Good boat
95%
Recommended
86%
Caught fish

All reviews (224)

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Showing 15 of 224 reviews
Michael Sellers
Michael Sellers
us
Virginia, US
Member since 2026
0
5.0
Verified
New
Great fishing experience.
Half Day Trip - 1:00 PM on May 2, 20268 adults
Took my son on this charter as part of his bachelor party. Weather forecast was iffy but the Captain made the call to proceed and it couldn't have been more perfect. Captain John was personable and made it fun. Mates were awsome unhooking fish and keeping bait on the hook. Boat was a nice size and covered for the ride. Four winds was five stars!
Response from Captain
May 2, 2026
hey, thanks for the great review we appreciate it 
Jason Foster
Jason Foster
us
Pennsylvania, US
Member since 2025
0
5.0
Verified
New
Fantastic family trip. Good times and tight lines, fish on!
3/4 Day Trip on May 18, 20267 adults
We had an amazing time out with the Captain and crew. Great conversation, great music and the weather was perfect. The boat was spacious for our group of 7, clean bathroom and shelter available if it would happen to rain or be too sunny for anyone. I would highly recommend them for your next trip.
Reported catch:
Bluefish (Tailor)
Spanish Mackerel
James Thompson
James Thompson
us
Virginia, US
Member since 2026
0
5.0
Verified
New
Terrific Trip!
Half Day Trip - 1:00 PM on May 16, 20265 adults
We had a terrific and great time. Smooth ride out and back, we caught fish even though it was a slow period (water a bit too cold). The captain and mate were exceptional, personable and fun to be around. This is a great trip to book for anyone. Future bookers should be mindful of 64 traffic when heading down.
Reported catch:
Atlantic Croaker
Response from Captain
May 17, 2026
thanks for the great review yes hopefully one day probably not in my lifetime will they ever finish the road construction around here
Dustin Bivins
Dustin Bivins
us
Virginia, US
Member since 2025
1
5.0
Verified
Captain John and Tim
Half Day Trip 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!
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
Brett VanBuren
Brett VanBuren
us
New York, US
Member since 2026
0
5.0
Verified
New
Great team!
3/4 Day Trip on May 16, 202610 adults
Went with a group of 12 guys and had the time of our lives. Captain and first mate were top knotch. Would book again. Caught a ton of croakers which we were happy with given the time of year we went.
Response from Captain
May 17, 2026
hey thanks for the great review and the sandwich was great too

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
May 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
2 hour trip starts at 7:00 PM
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US $550
Entire boat: up to 6 people
3 Hour Kids Trip (PM)
3 hour trip starts at 5:00 PM
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US $660
Entire boat: up to 6 people
Half Day Trip
4 hour trip multiple starting times (7:00 AM, 1:00 PM, 3:00 PM, 5:00 PM)
Seasonal trip
Apr 24 - Oct 31
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US $770
Entire boat: up to 6 people
3/4 Day Trip – Fall
6 hour trip starts at 6:30 AM
Seasonal trip
Oct 31 - Dec 31
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US $990
Entire boat: up to 6 people
3/4 Day Trip – Striper Trolling
6 hour trip starts at 6:30 AM
Seasonal trip
Oct 31 - Dec 31
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US $990
Entire boat: up to 6 people
3/4 Day Trip
6 hour trip starts at 7:00 AM
Seasonal trip
Apr 24 - Oct 31
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US $990
Entire boat: up to 6 people
Chesapeake Bay Shark Fishing (copy)
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 6 people
Chesapeake Bay Shark Fishing
6 hour trip multiple starting times (6:00 AM, 8:00 AM)
Seasonal trip
May 18 - Sep 30
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US $1,200
Entire boat: up to 6 people
Full Day Trip – Fall
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 6 people
Full Day Trip – Summer
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 6 people
There are 47 people looking at this charter.

Rating

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

Anglers' gallery (277)

What anglers say

93%
Great experience
98%
Family friendly
98%
Friendly captain
99%
Good boat
95%
Recommended
86%
Caught fish

All reviews (224)

Filter
Frequently mentioned
Loading...Loading...Loading...Loading...Loading...Loading...Loading...Loading...
Showing 15 of 224 reviews
Michael Sellers
Michael Sellers
us
Virginia, US
Member since 2026
0
5.0
Verified
New
Great fishing experience.
Half Day Trip - 1:00 PM on May 2, 20268 adults
Took my son on this charter as part of his bachelor party. Weather forecast was iffy but the Captain made the call to proceed and it couldn't have been more perfect. Captain John was personable and made it fun. Mates were awsome unhooking fish and keeping bait on the hook. Boat was a nice size and covered for the ride. Four winds was five stars!
Response from Captain
May 2, 2026
hey, thanks for the great review we appreciate it 
Jason Foster
Jason Foster
us
Pennsylvania, US
Member since 2025
0
5.0
Verified
New
Fantastic family trip. Good times and tight lines, fish on!
3/4 Day Trip on May 18, 20267 adults
We had an amazing time out with the Captain and crew. Great conversation, great music and the weather was perfect. The boat was spacious for our group of 7, clean bathroom and shelter available if it would happen to rain or be too sunny for anyone. I would highly recommend them for your next trip.
Reported catch:
Bluefish (Tailor)
Spanish Mackerel
James Thompson
James Thompson
us
Virginia, US
Member since 2026
0
5.0
Verified
New
Terrific Trip!
Half Day Trip - 1:00 PM on May 16, 20265 adults
We had a terrific and great time. Smooth ride out and back, we caught fish even though it was a slow period (water a bit too cold). The captain and mate were exceptional, personable and fun to be around. This is a great trip to book for anyone. Future bookers should be mindful of 64 traffic when heading down.
Reported catch:
Atlantic Croaker
Response from Captain
May 17, 2026
thanks for the great review yes hopefully one day probably not in my lifetime will they ever finish the road construction around here
Dustin Bivins
Dustin Bivins
us
Virginia, US
Member since 2025
1
5.0
Verified
Captain John and Tim
Half Day Trip 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!
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
Brett VanBuren
Brett VanBuren
us
New York, US
Member since 2026
0
5.0
Verified
New
Great team!
3/4 Day Trip on May 16, 202610 adults
Went with a group of 12 guys and had the time of our lives. Captain and first mate were top knotch. Would book again. Caught a ton of croakers which we were happy with given the time of year we went.
Response from Captain
May 17, 2026
hey thanks for the great review and the sandwich was great too

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
2023
Boat manufacturer
Evans
Boat type
Downeast
Engine model
Cummins
Powered by
2 x 225HP
Max cruising speed
22 knots
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