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Expert-Guided Full Day Fishing in Chesapeake Bay

  • Published Date: August 19, 2025
  • Fishing
  • $250 - $900 price range
  • Updated Date: August 21, 2025

Summary

Ready for a full day of fishing on the Chesapeake Bay? Captain Wayne Webb's 8-hour trip gives you plenty of time to target a variety of species. Starting at 8 AM, you'll head out to prime spots for bluefish, cobia, sheepshead, and tautog. This private charter is ideal for serious anglers or groups who want to make the most of their time on the water. With a 4-person capacity, there's room for you and your fishing buddies to spread out and cast. Whether you're after a specific catch or just want to enjoy a day on the bay, Captain Wayne knows where the fish are biting. You'll get hands-on experience with different techniques as you try for various species throughout the day. Pack some snacks, grab your sunscreen, and get ready for a full day of fishing action on the Chesapeake.
Expert-Guided Full Day Fishing in Chesapeake Bay

Chesapeake Catches

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Three people fishing in Hampton

On the hunt for the big one.

Fishermen with a cobia catch in Hampton

Hooks, bait, and a little fate.

three people fishing with two fish in va

Today’s agenda: fish and relax.

Two cobia fish caught in Hampton, Virginia

A tug on the line makes everything fine.

Four anglers enjoying a day of fishing in Hampton

Reeling in sunshine and smiles.

Two cobia fish caught during a fishing trip in Hampton

Big catches, bigger stories.

Two cobia fish caught in Hampton, Virginia

Tides change, fishing stays.

Cobia fish caught by fisherman in Hampton

The water is my happy place.

3 ladyfish caught while fishing in VA

Catch more than fish — catch moments.

A group of 4 people fishing in Hampton

Boat life, best life.

Three people fishing in Hampton

On the hunt for the big one.

Fishermen with a cobia catch in Hampton

Hooks, bait, and a little fate.

three people fishing with two fish in va

Today’s agenda: fish and relax.

Two cobia fish caught in Hampton, Virginia

A tug on the line makes everything fine.

Four anglers enjoying a day of fishing in Hampton

Reeling in sunshine and smiles.

Two cobia fish caught during a fishing trip in Hampton

Big catches, bigger stories.

Two cobia fish caught in Hampton, Virginia

Tides change, fishing stays.

Cobia fish caught by fisherman in Hampton

The water is my happy place.

3 ladyfish caught while fishing in VA

Catch more than fish — catch moments.

A group of 4 people fishing in Hampton

Boat life, best life.

Three people fishing in Hampton

On the hunt for the big one.

Fishermen with a cobia catch in Hampton

Hooks, bait, and a little fate.

three people fishing with two fish in va

Today’s agenda: fish and relax.

Two cobia fish caught in Hampton, Virginia

A tug on the line makes everything fine.

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Reel in a Full Day of Chesapeake Bay Action

Ready to spend a full day chasing some of the Chesapeake's finest? Captain Wayne Webb's got you covered with this 8-hour fishing trip that'll have you casting lines from sunup to sundown. Whether you're after hard-fighting bluefish or hoping to tangle with a beast of a cobia, this full-day adventure gives you the time and space to really dig into what the Bay has to offer. It's perfect for serious anglers looking to max out their time on the water or groups wanting to make a day of it. We'll leave the dock at 8 AM sharp, so grab your hat and let's hit the Bay!

What to Expect on the Water

When you step aboard Captain Wayne's boat, you're in for a treat. This isn't some cookie-cutter charter – it's a full 8 hours of customized fishing action. We'll start by getting a feel for what's biting and where the fish are holding. Some days that might mean we're running and gunning for bluefish, other days we might set up on structure to target tautog or sheepshead. The beauty of a full day is we've got time to try different spots and techniques. Don't worry if you're new to this – Capt. Wayne's got years of experience and he'll make sure you're rigged up right and fishing effectively. And hey, if you need a break, there's plenty of time to kick back, enjoy the scenery, and soak in that Chesapeake Bay atmosphere.

Fishing Techniques & Hotspots

On this trip, we'll be pulling out all the stops. For bluefish, we might troll with surgical tubes or cast topwater lures into breaking schools – there's nothing quite like watching a blue crash a surface plug! If we're after cobia, we'll often sight-cast to these bruisers, so keep your eyes peeled for their distinctive brown shapes cruising near the surface. Tautog and sheepshead require a bit more finesse – we'll drop baits right on top of structure and you'll need to develop a feel for their light bites. Spadefish can be a blast on light tackle, and we might chum them up with clam bits. Captain Wayne knows all the local honey holes, from bridge pilings to oyster beds and artificial reefs. Trust me, by the end of the day, your arms will know they've been fishing!

Species You'll Want to Hook

Tautog, or "tog" as the locals call 'em, are one of the Chesapeake's prized catches. These buck-toothed bottom-dwellers are known for their tasty white meat and their knack for cutting lines on structure. They're most active in cooler months, so spring and fall are prime time. Tautog fishing is all about patience and a quick hookset – when you feel that distinctive tap-tap, it's go time!

Bluefish are the Bay's speed demons. These toothy critters will hit just about anything that moves and put up one heck of a fight. They show up in force come spring and stick around into fall. Blues are great for anglers of all levels – they're not picky eaters and they'll give you a real workout on medium tackle. Just watch those teeth when you're unhooking 'em!

Spadefish might look like something out of a tropical aquarium, but don't let their looks fool you – they're tough customers on light tackle. These disc-shaped oddballs show up in summer months around structure. They're known for their finicky feeding habits, but when you dial in the technique, it's non-stop action.

Sheepshead are the Bay's striped bandits, and they're as tricky to catch as they are good to eat. With human-like teeth perfect for crushing crabs and barnacles, these fish require some specialized tactics. They hang around structure and are most active in warmer months. Landing a big sheepshead is a real feather in any angler's cap.

Cobia are the heavyweight champs of the Chesapeake. These bruisers can top 100 pounds and will test every bit of your tackle and skill. They migrate into the Bay in late spring and stick around through summer. Sight-casting to cobia is one of the most exciting types of fishing you can do in these waters – it's like hunting on the ocean!

Why Anglers Keep Coming Back

Look, I could go on all day about the fish, but what really makes this trip special is the whole package. You're out there for a full 8 hours, which means you've got time to really settle in and enjoy the day. Maybe we start off chasing blues in the morning, switch it up for some structure fishing midday, then finish off sight-casting to cobia in the afternoon. Or heck, if we find the hot bite, we might just stick on 'em all day long. The point is, we've got options, and Captain Wayne's got the know-how to make the most of whatever the Bay throws our way. Plus, with a smaller group size of just 4 guests max, you're getting a real personalized experience. It's not about rushing to fill a quota – it's about having a quality day on the water and hopefully putting some fish in the box while we're at it.

Time to Book Your Spot

Alright, let's cut to the chase – if you're looking for the ultimate day of fishing on the Chesapeake, this is it. You've got a full 8 hours to work with, a seasoned captain who knows these waters like the back of his hand, and a shot at some of the Bay's most exciting species. Whether you're a seasoned angler looking to tick some species off your list or a group of friends wanting to make some memories, this trip's got you covered. Just remember to bring your A-game, because these fish won't catch themselves! Don't let this opportunity slip away – get in touch with Chasin' Wake Charters and lock in your date. The Bay's calling, and trust me, you'll want to answer this one.

Learn more about the animals

Bluefish

Bluefish are the bulldogs of the Chesapeake Bay. These aggressive predators typically run 3-10 pounds, but can hit 20 pounds or more. You'll find them churning up the water's surface, chasing schools of baitfish in both the bay and coastal waters. Bluefish are summer visitors, showing up in June and sticking around till October. Anglers love 'em for their hard-fighting spirit and the chaos they create when feeding. They'll hit just about any lure or bait that moves. For a real thrill, try topwater plugs during a blitz - that's when blues go into a feeding frenzy, thrashing at the surface. Just watch your fingers when unhooking them; those razor-sharp teeth are no joke. Pro tip: oily baits like menhaden or mackerel are bluefish magnets. Cut them into chunks and get ready for some fast action.

Bluefish

Cobia

Cobia are the bruisers of the Chesapeake Bay. These powerful fish average 30-50 pounds but can top 100. Often mistaken for sharks, they show up in late spring and stick around till fall. You'll find them near buoys, channel markers, and other structures, often just below the surface. Cobia are prized for their hard fights and excellent table fare. Sight fishing for them is a real thrill - keep your eyes peeled for their dark shapes cruising near the surface. They'll hit live eels, croakers, or big bucktail jigs. Here's a local tip: when you spot a cobia, cast well ahead of it and let your bait sink. Then, slowly retrieve it across the fish's path. Be ready for a powerful strike and a long, tough battle. Landing a big cobia is something you won't soon forget!

Cobia

Sheepshead

Sheepshead are the dentists of the Chesapeake Bay. These striped fish, nicknamed "convict fish," typically weigh 1-8 pounds but can reach up to 20. You'll find them around structures like docks, bridges, and reefs, using their human-like teeth to crunch barnacles and crabs. Spring through fall is prime time for sheepshead fishing. Anglers love the challenge - these guys are notorious bait stealers. They're also prized for their sweet, white meat. To catch one, use light tackle and small hooks. Fiddler crabs or pieces of clam work well as bait. Here's a local trick: scrape some barnacles off a piling to create a chum slick. This'll bring the sheepshead right to you. When you feel a nibble, wait a second, then set the hook hard. These fish have tough mouths, so you'll need to be quick and forceful.

Sheepshead

Spadefish

Spadefish are the oddballs of the Chesapeake Bay. These disk-shaped fish, with their distinctive black stripes, usually weigh 3-10 pounds. You'll find them around structure - reefs, wrecks, and even buoys. They show up in late spring and hang around till early fall. Spadefish are fun to catch because they school up and put up a surprising fight for their size. They're not the easiest to hook, but that's part of the challenge anglers love. These fish have small mouths, so use light tackle and small hooks. Clams are the go-to bait, but here's a local secret: try using small pieces of jellyfish. Spadefish can't resist them. When you spot a school, cast just beyond them and slowly retrieve your bait through the group. Be patient - it might take a few tries, but the reward is worth it.

Spadefish

Tautog

Tautog are a unique catch in the Chesapeake Bay. These stout, mottled fish average 1-3 pounds but can reach up to 28 pounds. They're structure-lovers, hanging around rocky areas, jetties, and wrecks. Tautog fishing really picks up in spring and fall when water temps are cooler. They put up a stubborn fight, using their powerful jaws and teeth to crush shellfish - and your hooks if you're not careful. Anglers love targeting them for their tasty white meat. To land one, use a sensitive rod with a stiff backbone and bait up with green crabs or Asian crabs. Here's a local tip: crush some crab legs and sprinkle the bits around your fishing spot. This creates a scent trail that'll bring the tautog right to you. Just be ready for a tug-of-war when you hook one!

Tautog

About the 23’ Mako

Company vehicle

Vehicle Guest Capacity: 4

Manufacturer Name: Suzuki

Maximum Cruising Speed: 35

Number of Engines: 1

Horsepower per Engine: 250

Captain Wayne Webb's full-day fishing trip on the Chesapeake Bay is a chance to truly immerse yourself in the diverse angling opportunities of these rich waters. Setting out at 8:00 AM for a solid 8 hours on the bay, you'll have ample time to target a variety of prized catches. Whether you're after the hard-fighting bluefish, the sought-after cobia, or aiming to land a sheepshead or tautog, this extended trip maximizes your chances for success. With room for up to 4 guests, it's an ideal outing for a group of friends or family looking to share a memorable day on the water. Captain Wayne's experience and local knowledge ensure you'll be fishing the most productive spots throughout the day. Pack a lunch, bring your favorite beverages, and get ready for a full day of casting, reeling, and hopefully, plenty of catching on the beautiful Chesapeake Bay.
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Embark on an exhilarating fishing adventure with Chasin’ Wake Charters, the top choice for memorable fishing trips on Chesapeake Bay. Guided by the expert Captain Wayne Webb, Chasin’ Wake Charters provides anglers of every skill level the chance to catch trophy fish while enjoying the breathtaking beauty of Chesapeake Bay's pristine waters. Dedicated to customer satisfaction and passionate about fishing, Chasin’ Wake Charters guarantees an unforgettable day on the water filled with excitement, camaraderie, and lasting memories.

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