Four Winds Chartering 

4.8
(267 reviews)
 368 Dandy Haven Road, Hampton, VA 23664, United States–

Four Winds Chartering 

Hampton, VA, United States
–
44 ft
19
4.8
(267 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.

Loading...

Select date to see availability

Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
Loading...
Group Size
2 adults • 0 children
Change
Almost there...
2 Hour – Sunset and Fishing Cruise
FREE Cancellation 30 days notice
2 hour trip starts at 7:00 PM
Loading...
Loading...
Loading...
US $660
Entire boat: up to 6 people
3 Hour Kids Trip (PM)
FREE Cancellation 30 days notice
3 hour trip starts at 5:00 PM
Loading...
Loading...
Loading...
US $770
Entire boat: up to 6 people
Half Day Trip
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
Loading...
Loading...
Loading...
US $880
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
Loading...
Loading...
Loading...
US $1,200
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
Loading...
Loading...
Loading...
US $1,250
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
Loading...
Loading...
Loading...
US $1,250
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
Loading...
Loading...
Loading...
US $1,250
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
Loading...
Loading...
Loading...
US $1,400
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
Loading...
Loading...
Loading...
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)
Loading...
Loading...
Loading...
US $1,440
Entire boat: up to 6 people

Customer reviews

Loading...

Rating

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

Anglers' gallery (352)

What anglers say

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

Reviews (267)

  • Hector Perez
    Hector Perez
    us
    New York, US
    Member since 2026
    5.0
    Verified

    Amazing family fun

    Half Day Trip - 5:00 PM on August 7, 2026 • 5 adults • 1 child

    We are truly grateful for the experience and honored to have spent our time aboard with Captain Jon O’Neill and his outstanding crew. We are reviewing this experience as a 100% recommendation for anyone seeking a great time fishing with their loved ones. The crew was welcoming and attentive to every need, allowing my family to create lasting memories. As it was my wife and son’s first fishing trip, it was important that they felt comfortable; when we hit some rough water and my son became frightened and seasick, Captain Jon’s steady presence and ability to guide us into calmer waters saved the day. My son ended up spending a good portion of the trip happily hanging out with the Captain. Jon’s knowledge of the waters was great, leading us to the perfect pockets where we kept reeling them in. We look forward to our next outing and will definitely be returning.

  • Tanya Wilson
    Tanya Wilson
    us
    Massachusetts, US
    Member since 2026
    5.0
    Verified

    Great time!

    Half Day Trip - 1:00 PM on September 20, 2026 • 13 adults • 8 children

    We had a great time! We were celebrating my son’s birthday, and a group of us went out fishing with Captain John. 🎣 Everyone caught a fish, which made the day even more special! Captain John and Ms. Savanna were both incredibly nice, helpful, and made sure everyone had a wonderful experience. We had such a fun time celebrating and making great memories together. We’re definitely looking forward to doing it again! Highly recommend! ⭐️⭐️⭐️⭐️⭐️

  • David Daugherty
    David Daugherty
    Repeat angler
    us
    Pennsylvania, US
    Member since 2025
    2 trips
    5.0
    Verified

    Great Fishing on 4 Hour Charter

    Half Day Trip on August 1, 2026 • 5 adults

    My family and I were looking for a few hours of bay fishing, and Four Winds Chartering delivered a great day on the water. We weren't after any particular species — just wanted to catch fish — and the captain and crew came through. Bottom rigs brought in Croaker, Sea Bass, and Toadfish, while trolling landed us a Bluefish and several Spanish Mackerel. The crew was fantastic from start to finish. Highly recommend Four Winds Chartering for anyone looking to fish the bay. Thank you!

  • Lisa Regan
    Lisa Regan
    us
    Virginia, US
    Member since 2026
    5.0
    Verified

    Great Fishing!

    Half Day Trip on June 29, 2026 • 3 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!

  • Denise Zapf
    Denise Zapf
    us
    Virginia, US
    Member since 2026
    5.0
    Verified

    First Time; Won’t Be the Last

    3/4 Day Trip on September 19, 2026 • 7 adults

    Captain John brought us out to the bay in time for a beautiful sunrise and then put us on the Spanish Mackerel. Later we moved to calmer waters and caught spot, croaker and a few funny puffer fish. The seven of us had a giant feast of grilled mackerel and froze more than we ate.

  • Dalton Jevnick
    Dalton Jevnick
    us
    Pennsylvania, US
    Member since 2026
    5.0
    Verified

    Fishing with John

    Half Day Trip on June 30, 2026 • 3 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

  • Justin Garcia
    Justin Garcia
    us
    New Mexico, US
    Member since 2026
    5.0
    Verified

    Great time had by all!

    Half Day Trip - 1:00 PM on June 17, 2026 • 5 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!

  • Justin Chapman
    Justin Chapman
    us
    Virginia, US
    Member since 2026
    5.0
    Verified

    A great day on the water!

    3 Hour Kids Trip (PM) on June 13, 2026 • 5 adults • 2 children

    It was an amazing time! The captain and his mate savanna were amazing. We had 6 kids with us and none of them went without bait or anything. Would definitely recommend. If you want to catch fish and have a good time while you do it Four winds chartering is the way to go!!

  • Warren Aldredge
    Warren Aldredge
    us
    Virginia, US
    Member since 2026
    5.0
    Verified

    First outing with Grandkid’s

    Half Day Trip - 5:00 PM on September 7, 2026 • 5 adults • 2 children

    Captain John and mate were excellent! Patient with the kids and put us on the fish! At the end of the trip my grandson asked if we could do this yearly and my granddaughter sand twice a year! Highly recommend Captain and crew.

  • Mike Sanofsky
    Mike Sanofsky
    us
    Illinois, US
    Member since 2025
    5.0
    Verified

    Fishing with John

    Half Day Trip on September 7, 2026 • 6 adults

    Great experience with my daughters and family will definitely use them again. Crew and captain were excellent and super friendly! We got to do a bit of trolling and fishing off the bottom, much more unique and fun than just trolling!

Rating

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

Anglers' gallery (352)

What anglers say

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

All reviews (267)

Frequently mentioned
Loading...Loading...Loading...Loading...Loading...Loading...Loading...Loading...
Showing 1 – 5 of 267 reviews
Ora Williams
Ora Williams
us
Virginia, US
Member since 2026
5.0
Verified
Fishing with John
2 Hour – Sunset and Fishing Cruise on September 2, 2026 • 3 adults

We had an absolutely amazing experience on this boat! Captain John and his staff were incredible, and I truly couldn’t have asked for a better fishing experience. The boat was clean, comfortable, and welcoming, and the entire crew was friendly and professional. It was such an amazing trip from start to finish! I would definitely recommend this experience to anyone looking for a fun family outing, a day on the water, or simply a great fishing adventure. Thank you, John, and the entire team, for making our trip so memorable. We will definitely be returning soon! 🎣🚤 Highly recommend!

Hector Perez
Hector Perez
us
New York, US
Member since 2026
5.0
Verified
Amazing family fun
Half Day Trip - 5:00 PM on August 7, 2026 • 4 adults • 1 child

We are truly grateful for the experience and honored to have spent our time aboard with Captain Jon O’Neill and his outstanding crew. We are reviewing this experience as a 100% recommendation for anyone seeking a great time fishing with their loved ones. The crew was welcoming and attentive to every need, allowing my family to create lasting memories. As it was my wife and son’s first fishing trip, it was important that they felt comfortable; when we hit some rough water and my son became frightened and seasick, Captain Jon’s steady presence and ability to guide us into calmer waters saved the day. My son ended up spending a good portion of the trip happily hanging out with the Captain. Jon’s knowledge of the waters was great, leading us to the perfect pockets where we kept reeling them in. We look forward to our next outing and will definitely be returning.

Reported catch:
Spanish Mackerel
Atlantic Croaker
Sarah Penrod
Sarah Penrod
us
Ohio, US
Member since 2026
5.0
Verified
We want to do this again!
3 Hour Kids Trip (PM) on July 14, 2026 • 3 adults • 3 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
Tanya Wilson
Tanya Wilson
us
Massachusetts, US
Member since 2026
5.0
Verified
Great time!
Half Day Trip - 1:00 PM on September 20, 2026 • 5 adults • 8 children

We had a great time! We were celebrating my son’s birthday, and a group of us went out fishing with Captain John. 🎣 Everyone caught a fish, which made the day even more special! Captain John and Ms. Savanna were both incredibly nice, helpful, and made sure everyone had a wonderful experience. We had such a fun time celebrating and making great memories together. We’re definitely looking forward to doing it again! Highly recommend! ⭐️⭐️⭐️⭐️⭐️

David Daugherty
David Daugherty
Repeat angler
us
Pennsylvania, US
Member since 2025
2 trips
5.0
Verified
Great Fishing on 4 Hour Charter
Half Day Trip on August 1, 2026 • 5 adults

My family and I were looking for a few hours of bay fishing, and Four Winds Chartering delivered a great day on the water. We weren't after any particular species — just wanted to catch fish — and the captain and crew came through. Bottom rigs brought in Croaker, Sea Bass, and Toadfish, while trolling landed us a Bluefish and several Spanish Mackerel. The crew was fantastic from start to finish. Highly recommend Four Winds Chartering for anyone looking to fish the bay. Thank you!

Reported catch:
Bluefish (Tailor)
Spanish Mackerel
Atlantic Croaker

FAQs about Four Winds Chartering

Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading
Loading

The fish you can target

Loading
Loading

Real catches by this captain

  • Loading...
  • Loading...
  • Loading...
  • Loading...

What is the boat like?

Boat image
Boat category
Cabin cruisers
Capacity
19 persons
Boat length
44 ft
Year built
1997
Boat manufacturer
Evans
Boat type
Downeast
Engine model
Cummins
Powered by
2 x 225HP
Max cruising speed
22 knots
Loading
Loading
Loading
Loading
Loading

What’s biting in Hampton right now

Loading

Compare similar fishing charters

Loading...
Loading...
Loading...