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Premier Chesapeake Bay Fishing Charters | 2-8 Hours
- Published Date: July 16, 2025
- Fishing
- $250 - $900 price range
- Updated Date: August 21, 2025
Summary
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Sunset Catches
On the hunt for the big one.
Hooks, bait, and a little fate.
Today’s agenda: fish and relax.
A tug on the line makes everything fine.
Reeling in sunshine and smiles.
Big catches, bigger stories.
Tides change, fishing stays.
The water is my happy place.
Catch more than fish — catch moments.
Boat life, best life.
On the hunt for the big one.
Hooks, bait, and a little fate.
Today’s agenda: fish and relax.
A tug on the line makes everything fine.
Reeling in sunshine and smiles.
Big catches, bigger stories.
Tides change, fishing stays.
The water is my happy place.
Catch more than fish — catch moments.
Boat life, best life.
On the hunt for the big one.
Hooks, bait, and a little fate.
Today’s agenda: fish and relax.
A tug on the line makes everything fine.
Cast & Relax: Evening Fishing on Chesapeake Bay
Ready for a quick escape on the water? This 2-hour sunset fishing trip on Chesapeake Bay is the perfect way to unwind after a long day. Whether you're a seasoned angler or just looking to wet a line, Captain Jim at Chasin' Wake Charters has got you covered. Grab the family, pack some snacks, and get ready to make some memories as the sun dips below the horizon.
Trip Overview
You'll meet up with the captain at 6:30 PM, just as the day's heat starts to fade. The boat's all prepped and ready to go – no need to fuss with gear or bait. As you cruise out onto the Bay, keep an eye out for ospreys diving for their dinner or dolphins playing in the wake. The captain knows all the honey holes where fish like to hang out as evening sets in. You might drop anchor near a rocky outcropping or drift along a channel edge. Either way, you're in for some laid-back fishing and gorgeous views. With room for up to 4 guests, it's ideal for small groups or families looking to spend some quality time together on the water.
What to Expect on the Water
This trip is all about light tackle fishing – perfect for anglers of all skill levels. The captain will get you set up with rods, reels, and the right bait for whatever's biting. You might be tossing soft plastics for bluefish one minute, then switching to cut bait for sheepshead the next. Don't worry if you're new to fishing; the crew's always happy to show you the ropes. They'll teach you how to cast, set the hook, and reel in your catch like a pro. And if you're an old hand? Feel free to bring your favorite rod along. As the sun starts to set, the Bay takes on a whole new character. The water turns to liquid gold, and the fish often get more active. It's the perfect time to be out there, rod in hand, waiting for that telltale tug on the line.
Species You'll Want to Hook
Bluefish: These guys are the fireworks of the fishing world. Known for their aggressive strikes and hard-fighting spirit, bluefish can turn a quiet evening into an adrenaline-pumping adventure in seconds. They usually show up in the Bay from spring through fall, with peak action in the summer months. Bluefish travel in schools, so when you find one, you've often found a whole bunch. They're great fun on light tackle, and their oily flesh makes them perfect for smoking if you want to take some home for the grill.
Sheepshead: Don't let their goofy-looking teeth fool you – these striped battlers are no joke to catch. Sheepshead are masters of structure, hanging around pilings, rocks, and oyster beds. They're known for their light bite and ability to steal bait, making them a true test of an angler's skills. The satisfaction of hooking one of these crafty fish is hard to beat. They're around most of the year but really pick up in the warmer months. As a bonus, they're excellent eating fish with firm, white flesh.
Cobia: The prize catch of many Chesapeake Bay anglers, cobia are like the supermodels of the fishing world – they don't show up often, but when they do, everyone gets excited. These powerful fish start showing up in the Bay in late spring and stick around through early fall. They can grow to over 100 pounds, though most are in the 30-50 pound range. Cobia love to follow rays, so keep an eye out for those "sea pancakes" gliding through the water. Hooking a cobia on this trip would be like hitting the jackpot – it doesn't happen every day, but it's always possible.
Tautog: Often called "tog" or "blackfish," these wrasse family members are the tough guys of the Bay. They hang out around hard structure like wrecks, reefs, and rocky areas. Tautog fishing is all about finesse and timing – they have a quick, subtle bite that can be tricky to detect. But once hooked, they put up a stubborn fight that'll test your gear and your patience. They're around year-round but are most active in cooler months. Tautog are prized for their tasty white meat, often compared to lobster in flavor.
Spadefish: These distinctive-looking fish with vertical black bars are a unique catch in the Bay. They show up in late spring and hang around until early fall, often forming large schools around structure. Spadefish can be finicky eaters and challenging to hook, but they're a blast on light tackle. They might look small, but don't be fooled – these pancake-shaped fighters can really pull when hooked. While not as well-known as some other Bay species, catching a spadefish is always a memorable experience.
Why Anglers Keep Coming Back
There's something special about fishing as the day winds down. The water calms, the air cools, and the fish often get more active. It's a chance to decompress, connect with nature, and maybe land a few fish for dinner. But what really sets this trip apart is the flexibility. Got kids with short attention spans? No problem – the 2-hour timeframe is perfect. New to fishing and don't want to commit to a full day? This is your ideal intro. Even for experienced anglers, sometimes you just want to sneak in a quick session after work. And let's be honest, watching the sunset over the Bay while you're reeling in a fish? That's hard to beat.
Time to Book Your Spot
Look, we all need a break sometimes. And this trip? It's like a mini-vacation you can squeeze into a weeknight. No need to take time off work or plan for weeks. Just show up, hop on the boat, and let the stress melt away as you cast your line into the golden waters of Chesapeake Bay. Whether you're looking to introduce the kids to fishing, impress a date with a unique evening out, or just need some "you time" on the water, this trip fits the bill. The hardest part will be deciding who gets to reel in the big one. So why wait? Grab your favorite snacks, maybe a cold drink or two, and book your spot on this sunset fishing adventure. The fish are waiting, and so is your perfect evening on the Bay.
Learn more about the species
Bluefish
Bluefish are one of the Bay's hardest-fighting fish, pound for pound. These toothy predators show up in late spring, sticking around until fall when water temps drop. Look for them busting bait on the surface - that's the "bluefish blitz" in action. Blues run 3-5 pounds on average but can top 20. They'll hit just about any lure, but metal spoons and topwater poppers are local favorites. When they're in a frenzy, blues will attack anything that moves. Watch those razor-sharp teeth when unhooking them. Bluefish make great sport on light tackle. Their aggressive strikes and acrobatic jumps are a blast. For eating, bleed and ice them quickly. Smaller ones under 5 pounds taste best. Try grilling fresh bluefish steaks with lemon - delicious! During summer, we often find them around the Bay Bridge or cruising the shallows.
Cobia
Cobia are the bruisers of the Bay, often mistaken for sharks with their long, sleek bodies. These fish are loners, so spotting one is always exciting. They show up in late spring, hanging around through summer. Most run 20-40 pounds, but 60+ pounders aren't uncommon. Look for them near buoys, channel markers, and other structure, often just below the surface. Cobia are curious fish - they'll investigate splashes and commotion. Try live eels, big bucktail jigs, or sight-cast with large swimbaits. When hooked, cobia put up a grueling fight with powerful runs. They're excellent eating too, with firm, white meat. Here's a local secret: on calm days, cruise the shallows looking for rays. Cobia often follow them, picking off crabs and small fish the rays kick up.
Sheepshead
Sheepshead are the Bay's toothy bandits, known for their human-like chompers and convict stripes. Most run 2-5 pounds, but 10+ pounders turn up around deeper structures. You'll find them hanging around bridge pilings, reefs, and docks, crushing crabs and barnacles with those powerful jaws. Sheepshead are masters at stealing bait, so bring your A-game. Use a small, strong hook with fiddler crabs or pieces of clam. When you feel that telltale nibble, set the hook fast and hard. These fish put up a stubborn fight, often trying to wrap you around pilings. The challenge of hooking them, combined with their excellent table fare, makes sheepshead a favorite target. Pro tip: Scrape some barnacles off pilings to chum them up. Peak season is late summer through fall when water temps start cooling off.
Spadefish
Spadefish are one of the Bay's most unique-looking catches. With their disc-shaped bodies and bold black stripes, they're sometimes called "angelfish." Most run 3-5 pounds, but 10+ pounders aren't unheard of. You'll find them around structure like bridge pilings, buoys, and wrecks from late spring through early fall. Spadefish travel in large schools, so when you find them, the action can be non-stop. They're notorious bait stealers, so use small hooks and be ready for subtle bites. Fresh clam strips or small pieces of jellyfish work well. Despite their size, spades put up a scrappy fight on light tackle. Their firm white meat is excellent eating too. Here's a local trick: Chum with bits of clam to keep a school interested, then drop your bait right in the middle of the frenzy.
Tautog
Tautog, also called blackfish, are a tough, structure-loving fish that'll give you a real workout. These bruisers typically run 1-3 pounds but can get up to 20+. You'll find them around rocks, wrecks, and pilings in the Bay, especially in cooler months. They've got powerful jaws full of teeth for crushing crabs and shellfish, so bring sturdy gear. Tautog put up a stubborn fight, often trying to dive back into their rocky homes. For best results, use green crabs or clams on a fishfinder rig with a short leader. Work it slowly right on the bottom. When you feel that telltale tap-tap, set the hook hard - these guys have tough mouths. The meat is white, flaky, and delicious, making tautog a prized catch for the dinner table too.
