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Four Winds Chartering

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374 Dandy Haven Road Hampton, VA

If you’re looking for first class Chesapeake Bay Fishing Charters, you have come to the right place. Four Winds Chartering provides the best Chesapeake Bay fishing charters and Hampton fishing trips in Virginia. Four Winds Chartering is located in the finest sport fishing location on the East ...

If you’re looking for first class Chesapeake Bay Fishing Charters, you have come to the right place. Four Winds Chartering provides the best Chesapeake Bay fishing charters and Hampton fishing trips in Virginia. Four Winds Chartering is located in the finest sport fishing location on the East Coast and is based out of Hampton, VA.

At the helm is Captain John O’Neal, an expert Chesapeake Bay Charter Fishing Captain with over 20 years of experience. Climb aboard the beautiful 42’ Bay Boat and fish in comfort with your group – whether it’s 1 or 27! Powered by a 225HP Detroit engine, this clean and safe vessel has clean restroom facilities, as well as a multimedia system and top navigational equipment. All safety equipment is U.S. Coast Guard certified (including life jackets, life raft, First Aid Equipment, Flares, VHF Radio, and EPIRB) – we also have CPR-Trained Crew.

Custom Group Charters are our specialty! We are the only Chesapeake Bay boat approved by the U.S. Coast Guard to take groups up to 27 for ocean trips. We fish just about year round, 7 days a week! If you’re looking for bottom fishing, deep sea fishing, drift fishing, or trolling the Chesapeake Bay, we are able to accommodate your next fishing trip!

With Four Winds Chartering you fish for Fall Stripers, Cobia, Croaker, Spot Flounder, Bluefish, Sea Trout, Sea Mullet, Oyster Toad, Sand Shark, and More! We offer 4 hour fishing trips, 6 hour fishing trips, and 8 hour fishing trips – all include exceptional service, rods, reels, tackle & bait, fishing licenses for all anglers, and over 20 years of experience from a Captain and Crew that love fishing! You will want to bring sun block, sunglasses, hat, and your camera. Small coolers are okay. Make sure your personal items are secured (crew is not responsible for lost items).

Your next Chesapeake Bay Fishing Charter will be fun and exciting if you book with Captain John and Four Winds Chartering. You and your fellow anglers will have a safe day on the water, and a successful day of fishing – with stories that you’ll be sure to share with friends & family! Don’t wait… book your next Chesapeake Bay Fishing trip today!

Popular Features:

  • Fishing License Included
  • Fish Cleaning Included
  • Toilet On Board
  • Children Welcome
  • Fishing Tackle Included
  • First Mate

  • Fishing Trips with Four Winds Chartering start at: $550.00

    View Trips

  • Your Captain will provide:

    • Catch Cleaning & Filleting
    • Fishing License
    • Fresh or Live Bait
    • Lures
    • Rods Reels Terminal Tackle

    You’ll need to bring drinks (no glass bottles), snacks, weather appropriate clothing, sunglasses, sunscreen, etc.

  • Weather cancellations are at your Captain’s discretion, your safety is their number one priority! You will receive a refund for any weather cancellation, or you can choose to reschedule your trip for a different date.

  • 374 Dandy Haven Road Hampton, VA

    • Cobia
    • Flounder
    • Spanish Mackerel
    • Striped Bass
    • Triggerfish
    • Weakfish
    • Black Drum
    • Bluefish
    • Spotted Seatrout
    • Tautog
    • Blue Fish
    Your Captain will have you targeting the species biting most frequently on the days leading up to your trip!

Trips:

You will have the opportunity to select backup dates in checkout (if applicable)

Evening Trip

$550.00

Price includes up to 6 guests

+$55.00 per additional guest, max 19 guests

6:00pm - 8:00pm EST (2 hours)
Deposit refundable up to 30 Days before the trip
Trip Details

This trip is 2 hours of fishing on the Chesapeake Bay. We'll go after everything from Flounder, Bluefish, and whatever else is in season. Captain John supplies all of the fishing gear. Flexible start time.

6HR (AM) Bottom Fishing Trip

$990.00

Price includes up to 6 guests

+$99.00 per additional guest, max 19 guests

7:00am - 1:00pm EST (6 hours)
Deposit refundable up to 30 Days before the trip
Trip Details

This is a six-hour bottom fishing trip for Croaker, Spot, Perch, and Trout. This trip includes bait, tackle, and licenses for up to 19 people. You should pack food and drinks, as well as sunglasses and sunscreen. This is a good trip for any fisherman that wants to spend a day on the water, any experience level welcome.

6HR (PM) Fishing Trip

$990.00

Price includes up to 6 guests

+$88.00 per additional guest, max 19 guests

1:00pm - 7:00pm EST (6 hours)
Deposit refundable up to 30 Days before the trip
Trip Details

*Start time is very flexible! Anywhere from 12pm-4pm, this is the trip for YOU*

If you prefer to be moving during the hot weather this may be the trip for you. You will troll briskly for Spanish Mackerel but if you want Blues mixed in they can slow just a bit. This is ideal if you don't want to sit in the same place with the sun baking you. Bring your food, drink, and proper attire. Sunglasses and sunscreen are a great idea, too. You will want a cooler to carry your catch home in.

Half Day Trip (AM)

$770.00

Price includes up to 6 guests

+$77.00 per additional guest, max 19 guests

7:00am - 11:00am EST (4 hours)
Deposit refundable up to 30 Days before the trip
Trip Details

Don't have a full day to spend on the water? This morning trip is for you. Leaving the dock at 6 AM and returning at 10 AM, you and up to 27 of your friends can enjoy time on the water and avoid the hottest part of the day. You will be fishing for Croaker, Spot, Trout, Mullet and several other species. All tackle, bait, and licenses are provided for you. Bring your sunglasses, sunscreen, food, beverages and a desire to have a good time!

Half Day Trip (PM)

$770.00

Price includes up to 6 guests

+$77.00 per additional guest, max 19 guests

4:00pm - 8:00pm EST (4 hours)
Deposit refundable up to 30 Days before the trip
Trip Details

Significant other or boss got your morning tied up? Play hooky for the afternoon. Newbie or pro, you will enjoy this relaxing trip for Croaker, Spot, Trout and Flounder. This unique after work special has a limited area you will fish, so you'll be home for dinner. All tackle, bait, and licenses are provided for you. Don't forget your food, beverages, and a desire to have a good time!

Full Day Trip

$1,440.00

Offered 11/01/24 - 12/31/24

Price includes up to 6 guests

+$99.00 per additional guest, max 19 guests

7:00am - 3:00pm EST (8 hours)
Deposit refundable up to 30 Days before the trip
Trip Details

Full day fishing trip striper trolling. This 8-hour trip departs the dock at 07:00 AM, so bring your camera if you like sunrises over the water. You will cruise the bay to the hot spots and get the lines in the water as fast as possible. You could be near CBBT, north to Wolf Trap or closer to the Eastern Shore, depending on where the fish are biting. License, reporting, and tackle are covered by the boat. Bring your food, drink, and proper attire for the day. Also, bring something to carry your catch home in.

Customer Reviews
Average Review
5
(18)
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Half Day Trip (PM)
Our family spent the afternoon with Captain John and his 2 mates Amber and C.J. We had a blast my 3 sons ages 9,12, and 15 will never forget this day. My husband and I appreciated how well CJ and Amber took the time to ensure that our boys experienced a true fishing expedition. You could tell that they love their jobs and want their charter guests to enjoy every aspect of this boating adventure. They were great at explaining the different types of fish we were looking to catch, their differing qualities and even showed the boys what noises they can make. Amber even got ahold of a blue crab to teach my youngest son about them. The boys not only caught a dozen plus fish that we were able to take home. We also had caught several non-edible fish to feed the birds on our return trip back to the marina. For all you women or men out there that don’t like cleaning fish, this was a total on vacation Mom/wife bonus for me…Amber cleaned, de-boned and filleted the fish. She packed up the fillets nicely into gallon zip loc bags so all we would need to do after getting them back home was cook them up. She has some serious fish fillet skills. Even my husband took notice. We felt safe in Captains Johns boat and he made an everlasting impression on us and we look forward to this becoming a yearly tradition with our family. If your looking for a great family adventure and enjoy the best that Hampton Roads area and its beautiful outdoors has to offer, then definitely pick this Charter boat and you will have an unforgettable adventure. This crew made this trip even more fun, their genuine fishing passion was very contagious and our entire family bonded with them. Thanks Captain John, Amber and C.J. for treating us like old friends and fish on! The Day family Justin,France, Sammy, Grayson and Cooper **hidden content**
Our family spent the afternoon with Captain John and his 2 mates Amber and C.J. We had a blast my 3 sons ages 9,12, and 15 will never forget this day. My husband and I appreciated how well CJ and Amber took the time to ensure that our boys experienced a true fishing expedition. You could tell that they love their jobs and want their charter guests to enjoy every aspect of this boating adventure. They were great at explaining the different types of fish we were looking to catch, their differing qualities and even showed the boys what noises they can make. Amber even got ahold of a blue crab to teach my youngest son about them. The boys not only caught a dozen plus fish that we were able to take home. We also had caught several non-edible fish to feed the birds on our return trip back to the marina. For all you women or men out there that don’t like cleaning fish, this was a total on vacation Mom/wife bonus for me…Amber cleaned, de-boned and filleted the fish. She packed up the fillets nicely into gallon zip loc bags so all we would need to do after getting them back home was cook them up. She has some serious fish fillet skills. Even my husband took notice. We felt safe in Captains Johns boat and he made an everlasting impression on us and we look forward to this becoming a yearly tradition with our family. If your looking for a great family adventure and enjoy the best that Hampton Roads area and its beautiful outdoors has to offer, then definitely pick this Charter boat and you will have an unforgettable adventure. This crew made this trip even more fun, their genuine fishing passion was very contagious and our entire family bonded with them. Thanks Captain John, Amber and C.J. for treating us like old friends and fish on! The Day family Justin,France, Sammy, Grayson and Cooper **hidden content**
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Half Day Trip (PM) (3PM)
I’d heartily recommend booking with Capt. John at Four Winds. We had a group of 3 dads and 5 boys age 12 and under. John and Amber (the first mate) were very friendly and helped the boys every step of the way during the charter. We had a great experience, whether trolling for mackerel or bottom fishing. This charter was better than another one we took out of North Carolina earlier this summer, as when we were bottom fishing everyone had their own line in the water, so all of the boys stayed engaged the entire time - especially since they were catching fish. Amber was great with the kids, helping with their bait if needed, unhooking the big fish (ones with sharp teeth!), and otherwise educating the boys about fish/fishing - including the process of fileting the fish at the end of the day. Both John and Amber were great and worked hard to get us on the fish. I’d definitely book with them again.
I’d heartily recommend booking with Capt. John at Four Winds. We had a group of 3 dads and 5 boys age 12 and under. John and Amber (the first mate) were very friendly and helped the boys every step of the way during the charter. We had a great experience, whether trolling for mackerel or bottom fishing. This charter was better than another one we took out of North Carolina earlier this summer, as when we were bottom fishing everyone had their own line in the water, so all of the boys stayed engaged the entire time - especially since they were catching fish. Amber was great with the kids, helping with their bait if needed, unhooking the big fish (ones with sharp teeth!), and otherwise educating the boys about fish/fishing - including the process of fileting the fish at the end of the day. Both John and Amber were great and worked hard to get us on the fish. I’d definitely book with them again.
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Full Day Trip – Summer
My friends and I wanted a day out on the water to just hang out and catch some fish. Unsurprisingly, that’s exactly what we got when we chartered with Four Winds. We showed up early to make sure we got as much time on the water as possible and had everything stowed just in time for our 7am launch. A quick safety brief and we were out on the bay in no time. Both Captain John and Amber were knowledgeable about the local ecosystem and readily pointed out lots of neat details about the areas we passed. As soon as we cleared the safe channels, the rods were brought out and set up to troll behind as we traveled to our first “spot.” As the mackerel started biting, the crew easily interacted with our group and the laughs were easy to come by as the day went on. We ended up stopping at 2 different fishing locations during the day and trolling for mackerel in between, but the fish were biting nearly the entire time. There was even a stretch of about an hour where nearly the entire group was getting constant hits on our lines. Every single member of our group that was fishing (and even one that hadn’t planned to fish at all) ended up landing a shark, and many “Baby Shark” memes were had. Near the end of the trip, the water started to get choppy, but it wasn’t anything our group had major issue with. Overall, it was an awesome day and every single person in our group had a blast! TL;DR - If you’re looking for a charter with a crew that’s fun to interact with, knows the waters, and is experienced as all get-out, then look no further! Four Winds Chartering is worth every penny.
My friends and I wanted a day out on the water to just hang out and catch some fish. Unsurprisingly, that’s exactly what we got when we chartered with Four Winds. We showed up early to make sure we got as much time on the water as possible and had everything stowed just in time for our 7am launch. A quick safety brief and we were out on the bay in no time. Both Captain John and Amber were knowledgeable about the local ecosystem and readily pointed out lots of neat details about the areas we passed. As soon as we cleared the safe channels, the rods were brought out and set up to troll behind as we traveled to our first “spot.” As the mackerel started biting, the crew easily interacted with our group and the laughs were easy to come by as the day went on. We ended up stopping at 2 different fishing locations during the day and trolling for mackerel in between, but the fish were biting nearly the entire time. There was even a stretch of about an hour where nearly the entire group was getting constant hits on our lines. Every single member of our group that was fishing (and even one that hadn’t planned to fish at all) ended up landing a shark, and many “Baby Shark” memes were had. Near the end of the trip, the water started to get choppy, but it wasn’t anything our group had major issue with. Overall, it was an awesome day and every single person in our group had a blast! TL;DR - If you’re looking for a charter with a crew that’s fun to interact with, knows the waters, and is experienced as all get-out, then look no further! Four Winds Chartering is worth every penny.
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Additional Features:

  • Saftey Equipment

  • Life Jackets
  • Life Raft
  • Fire Extinguishers
  • First-aid Equipment
  • Cpr-trained Crew
  • Epirb
  • Flares
  • Vhf Radio

  • Navigation

  • Gps
  • Fish Finder
  • Radar

  • Price Includes

  • Catch Cleaning & Filleting
  • Fishing License
  • Fresh Or Live Bait
  • Lures
  • Rods Reels Terminal Tackle
  • First Mate

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