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Expert-Guided Winter Flounder Fishing on Cape Cod Bay

  • Published Date: July 17, 2025
  • Fishing
  • Cape Cod, MA
  • $550 - $1,400 price range
  • Updated Date: September 20, 2025

Summary

Join Grey Dolphin Sportfishing Charters for a half-day winter flounder fishing trip on Cape Cod Bay. These 4-hour trips run in May and early June, with flexible morning or afternoon options to fit your schedule. Our experienced team welcomes anglers of all skill levels, from complete beginners to seasoned pros. We'll teach you the techniques to land some of the bay's best-tasting fish. With a small group size of just 5 guests, you'll get plenty of personalized attention and hands-on fishing time. The calm inshore waters are perfect for focusing on your catch without worrying about rough seas. Want more time on the water? We can arrange extended hours too. Grab your fishing buddies or bring the family for a fun day chasing flounder in one of New England's most scenic bays.
Expert-Guided Winter Flounder Fishing on Cape Cod Bay

Flounder Fishing Action

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Five people enjoying a day of fishing at Cape Cod

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Striped bass fishing in MA

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Single fisherman fishing in MA

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Striped Bass caught on fishing trip at Cape Cod

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Striped bass fishing in MA

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Striped bass caught while fishing in MA

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Striped bass caught while fishing in MA

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One striped bass caught on fishing trip in Cape Cod

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Two striped bass and white bass caught on a fishing trip in Cape Cod

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Group of 5 people fishing on the beach in Cape Cod

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Five people enjoying a day of fishing at Cape Cod

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Striped bass fishing in MA

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Single fisherman fishing in MA

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Striped Bass caught on fishing trip at Cape Cod

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Striped bass fishing in MA

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Striped bass caught while fishing in MA

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Striped bass caught while fishing in MA

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One striped bass caught on fishing trip in Cape Cod

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Two striped bass and white bass caught on a fishing trip in Cape Cod

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Group of 5 people fishing on the beach in Cape Cod

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Five people enjoying a day of fishing at Cape Cod

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Striped bass fishing in MA

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Single fisherman fishing in MA

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Striped Bass caught on fishing trip at Cape Cod

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Reel in Winter Flounder on Cape Cod Bay

Get ready to drop a line for some of the tastiest fish swimming in Cape Cod Bay! Our half-day winter flounder trips are perfect for anglers looking to squeeze in some quality fishing without taking up the whole day. Whether you're a local pro or just visiting, we've got the know-how to put you on the fish. May and early June is prime time for these flatfish, and we're itching to get you out there.

What's the Deal?

We're talking 4 hours of pure fishing action, folks. You can choose morning or afternoon trips, so it's easy to fit around your schedule. If you're really keen, we can even extend the trip for more time on the water. Our experienced crew will show you the ropes, from baiting up to bringing in your catch. And let me tell you, there's nothing quite like the fight of a good-sized flounder on light tackle.

Fishing the Flats

Winter flounder fishing is all about finesse. We'll be using light tackle and small hooks baited with sea worms or clams. The key is to find those sandy or muddy bottom areas where flounder like to hang out. We'll drift slowly, letting our baits bump along the bottom. When you feel that telltale thump, it's time to set the hook! Don't worry if you're new to this – our crew will walk you through every step, from casting to reeling in your catch.

Target Species

Winter Flounder, also known as blackback flounder, are the stars of this show. These flatfish might not look like much, but they're crafty and put up a good fight for their size. They usually run about 1-3 pounds, but we sometimes hook into 4-5 pounders that'll really test your skills. May and early June is when they're most active in the bay, feeding up before they head to deeper waters. Anglers love targeting these fish not just for the fun of catching them, but also because they're absolutely delicious. There's a reason they're called "tide runners" – they know how to use the current to their advantage, so be ready for some sneaky moves!

Why Anglers Keep Coming Back

Look, I've been guiding trips on Cape Cod Bay for years, and there's something special about flounder fishing that keeps folks coming back. Maybe it's the challenge of outsmarting these bottom-dwellers, or the satisfaction of filling a cooler with prime eating fish. Whatever it is, our half-day trips hit that sweet spot. You get enough time to really get into the groove, learn some new tricks, and hopefully land a few keepers. Plus, with our small group size of just 5 guests, you're getting personalized attention that you won't find on bigger party boats.

Time to Book Your Spot

So, are you ready to get in on some of the best flounder fishing Cape Cod has to offer? Our half-day trips are filling up fast, especially for those prime May and early June dates. Whether you're looking to introduce the kids to fishing, want a fun outing with friends, or just need to scratch that fishing itch, we've got you covered. Give us a call or book online – we'll make sure you're all set with gear, licenses, and everything you need for a great day on the water. Don't let this season's run pass you by – let's get out there and catch some flatties!

Learn more about the species

Winter Flounder

Winter flounder, also called blackbacks, are a unique catch in Cape Cod Bay. These right-eyed flatfish typically run 9-12 inches but can reach up to 25 inches and 8 pounds. You'll find them hanging out on sandy or muddy bottoms, often near vegetation where they blend in thanks to their chameleon-like ability to change color. May and early June are prime time for winter flounder fishing here. Anglers love targeting them for their delicate, sweet meat - some of the best-tasting in the bay. When fishing for these guys, remember they're morning feeders and rely on sight. Use larger baits like sea worms or clams, and bring a sensitive rod to detect their nibbling style. A local tip: try a 14-20 lb line. It might seem overkill, but you never know when you'll hook into that trophy blackback lurking in the weeds.

Winter Flounder

About the Grey Dolphin Sportfishing

Company vehicle

Vehicle Guest Capacity: 6

Manufacturer Name: Cummins

Maximum Cruising Speed: 16

Number of Engines: 1

Horsepower per Engine: 370

Ready for some winter flounder action on Cape Cod Bay? Join us for a 4-hour fishing trip in May and early June that's perfect for both early birds and afternoon adventurers. We've got flexible scheduling to fit your travel plans, and if you're hungry for more time on the water, we can extend the trip too. Our seasoned crew will show you the ropes, whether you're a pro angler or it's your first time holding a rod. Winter flounder are known for being some of the tastiest catches in the bay, so get ready to reel in some delicious dinner. With space for up to 5 guests, it's a great outing for families, friends, or solo fishers looking to join a fun group. Don't miss your chance to land these fantastic flatfish during their peak season in Cape Cod's beautiful waters.
Grey Dolphin Sportfishing Charters

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