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Premier Chesapeake Bay Fishing Charters | 2-8 Hours
- Published Date: July 16, 2025
- Fishing
- $250 - $900 price range
Summary
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Bay Fishing Moments
Saltwater, sunshine, and family love.
Good vibes only, out here on the ocean.
Living our best boat life with every trip.
Anchored in good times and great company.
Nothing beats a day on the water with Chasin’ Wake
Making memories, one cast at a time.
Big smiles, salty air, and fresh catches.
Captain Wayne leads the way to epic fishing days.
Chasing sunrises and trophy fish all day long.
Where every cast comes with a side of adventure.
Saltwater, sunshine, and family love.
Good vibes only, out here on the ocean.
Living our best boat life with every trip.
Anchored in good times and great company.
Nothing beats a day on the water with Chasin’ Wake
Making memories, one cast at a time.
Big smiles, salty air, and fresh catches.
Captain Wayne leads the way to epic fishing days.
Chasing sunrises and trophy fish all day long.
Where every cast comes with a side of adventure.
Saltwater, sunshine, and family love.
Good vibes only, out here on the ocean.
Living our best boat life with every trip.
Anchored in good times and great company.
Reel In Adventure on Chesapeake Bay
Hey there, fellow anglers! Ready to hit the water for some top-notch fishing action? Our private charters on Chesapeake Bay are just the ticket. Whether you're looking for a quick evening trip or a full day on the water, we've got options to fit your schedule. With trips ranging from 2 to 8 hours, you'll have plenty of time to cast your line and hopefully land some impressive catches. Our boat can accommodate up to 4 guests, so grab your buddies and let's get out there!
What to Expect on the Water
Picture this: You're cruising across the iconic Chesapeake Bay, rod in hand, with the salty breeze in your hair. Our trips kick off bright and early at 7 AM for those morning people, or if you prefer to sleep in, we've got afternoon departures at noon. For the night owls, our 2-hour sunset trips starting at 6:30 PM are perfect for catching that golden hour glow while you fish. And for those who want to make a full day of it, our 6 and 8-hour trips give you plenty of time to explore different fishing spots and really get into the groove.
On board, you'll find all the gear you need to target some of the Bay's most sought-after species. We're talking about tautog, bluefish, spadefish, sheepshead, and even the mighty cobia. Our experienced captain knows all the local hotspots and will put you right on top of the action. Just remember to pack some snacks and drinks, as meals aren't included in the trip.
Casting and Catching Tips
Alright, let's talk technique. Depending on what we're after, we might be bottom fishing for tautog or sheepshead around structure, or trolling for bluefish in open water. For those elusive cobia, sight fishing is often the name of the game. We'll show you how to work different baits and lures to entice these fish to bite. If you're new to fishing, don't sweat it – we'll walk you through everything from baiting your hook to setting the drag on your reel. And for you seasoned anglers, feel free to bring your favorite rod and we can swap fish stories while we wait for the big one to bite.
Species You'll Want to Hook
Tautog, or "tog" as we call 'em, are like the bulldogs of the bay. These tough fighters love to hang around rocky bottoms and sunken structure. They're notorious for their hard mouths and ability to bust your line on the nearest obstacle. But man, are they tasty! Best time to target these guys is in the cooler months, from fall through spring.
Bluefish are the speed demons of Chesapeake Bay. When a school of blues moves through, hold onto your rod! These toothy critters will hit just about anything that moves and put up one heck of a fight. They're most active in the warmer months, from late spring through early fall. Nothing beats the thrill of a topwater bluefish blitz!
Spadefish might look a bit funny with their disk-like bodies, but don't let that fool you. These striped fighters can pull hard for their size and often school up around buoys and wrecks. They're a summer specialty in the Bay, usually showing up in June and sticking around until September.
Sheepshead are the bay's escape artists. With their human-like teeth and zebra stripes, these fish are as unique as they come. They love to hang around pilings and bridges, using their chompers to crush crabs and barnacles. Catching a big sheepshead is a real feather in any angler's cap, and they're available from spring through fall.
Last but not least, we've got cobia. These bruisers can grow over 100 pounds and will test your stamina and your tackle. Cobia migrate into the Bay in late spring and stick around until early fall. Sight fishing for cobia is an adrenaline rush like no other – spotting that big brown shadow cruising near the surface and making the perfect cast... it's what fishing dreams are made of!
Time to Book Your Spot
So, what do you say? Ready to get out on the water and try your luck? Whether you're a seasoned pro or a first-timer, our Chesapeake Bay charters offer something for everyone. With flexible trip lengths and start times, we can accommodate even the busiest schedules. Don't miss out on the chance to create some lasting memories and maybe even catch your personal best. Give us a call or book online – the fish are waiting, and so are we!
Learn more about the species
Bluefish
Bluefish are aggressive predators that put up a serious fight. They typically range from 3 to 20 pounds, with some monsters hitting 40 pounds. You'll find them in the Bay from mid-June to mid-October, often churning up the water in feeding frenzies called "blitzes." These fish are fast swimmers with a mouthful of sharp teeth. They'll hit just about any bait or lure, making them exciting for anglers of all skill levels. Bluefish travel in schools, so when you find one, you've usually found many. Late summer is prime time for catching "snappers" – young bluefish that are perfect for introducing kids to fishing. For bigger blues, try tidal rivers and sandy harbors. Use oily bait like eel chunks or try fast-moving lures. Just watch those teeth when you're unhooking them – they can leave a nasty bite! Bluefish make good eating when prepared right, especially the smaller ones. Their aggressive nature and strong fight make them a favorite among sport fishers looking for an adrenaline rush.
Cobia
Cobia are the bruisers of the Chesapeake, often mistaken for sharks with their long, dark bodies. These solitary fighters average around 30-50 pounds but can grow to a whopping 100 pounds and 6 feet long. They show up in the Bay from late May through September, with peak fishing in July and August. You'll find cobia near structure like buoys, wrecks, and channels. They love hanging around rays, so keep an eye out for "cobia shadows" following big rays in shallow water. Sight fishing for cobia is a thrill – they're often visible just below the surface. Cobia put up an epic fight and make excellent table fare, which is why anglers get so excited about them. They're strong, unpredictable, and known for long runs and acrobatic jumps. To target cobia, live eels or large bucktail jigs work well. Cast ahead of the fish and retrieve slowly. When a cobia hits, hang on tight – these fish are notorious for their powerful initial run. Local tip: chum with cut menhaden to bring cobia to the surface, then sight cast to them. It's an exciting way to land one of the Bay's most prized catches!
Sheepshead
Sheepshead are the convicts of the Chesapeake, sporting distinctive black and white stripes. These fish typically run 1-8 pounds and 14-20 inches, though some giants can hit 20 pounds. They're structure-loving fish, hanging around docks, bridges, and reefs. Spring is prime time for sheepshead fishing, as they form massive spawning groups of up to 10,000 fish. Anglers prize them for their fight and excellent table fare – their white, sweet meat is delicious. To catch sheepshead, you've got to think like a crab. These fish have human-like teeth perfect for crushing shellfish. Use fiddler crabs, small stone crabs, or barnacles as bait. Get as close to structure as you can without spooking them. Here's a local trick: scrape some barnacles off the pilings to create a chum slick. The scent will draw sheepshead in. Be ready for subtle bites – these fish are masters at stealing bait. When you feel weight, set the hook hard. Their tough mouths and sneaky nature make landing a sheepshead a real accomplishment!
Spadefish
Spadefish are a unique catch in the Chesapeake, known for their disk-shaped bodies and striking black stripes. These silvery fish usually weigh 3-10 pounds and grow to about 18 inches, though some can reach 3 feet and 14 pounds. You'll find spadefish around structures like reefs, shipwrecks, and near the coastline. They're social creatures, often schooling in groups of 500 or more. Late spring through summer is prime time for spadefish in the Bay. Anglers love targeting spadefish for their surprisingly strong fight and the challenge they present. They're known for their finicky eating habits and can be tricky to hook. For bait, clams are your best bet. Use a small circle hook and cast just past the school, slowly dragging your bait through. Jellyfish chunks can work too. Be patient – spadefish are notorious nibblers. When you feel weight on the line, set the hook quickly. These fish may look docile, but they'll give you a run for your money once hooked!
Tautog
Tautog, or blackfish, are a unique catch in the Chesapeake. These stout, mottled fish average 1-3 pounds but can reach up to 28 pounds. They're structure-loving fish, hanging around rocks, wrecks, and jetties. Tautog are most active during the day, often lying on their sides at night. Spring and fall are prime seasons, with spawning happening from late April to early August. Anglers love tautog for their strong fight and tasty white meat. They're notoriously tricky to catch, thanks to their bait-stealing skills and tendency to dive into structure. To land one, use a sensitive rod with a sturdy backbone. Bait with green or Asian crab – crush some for chum. The scent drives tautog wild. Keep your bait fresh, changing every 4-5 minutes for best results. When you feel that distinctive nibble, set the hook hard. These fish have powerful jaws built for crushing shellfish, so be ready for a battle.
