Playin' Hooky Sportfishing Charters
Make an adventure out of your next trip to Sheboygan and go fishing with Playin’ Hooky Sportfishing Charters. Captain Dave is prepared to put you on fish.
These waters are known for Chinook Salmon, Coho Salmon, Lake Trout, Brown Trout, Rainbow Trout (Steelhead), and occasionally Pink Salmon – with any luck, it won’t take long to hook into some. On these trips, you can expect to troll.
Thinking of bringing the whole family? Kids are absolutely welcome! Children must wear life vests, and there are class 1 life vests on board. Feel free to bring your own if you like instead! And, you can’t go wrong with snacks for a boost of energy when needed!
You’ll be welcome aboard a 36’ Chris-Craft with room for 6 passengers. It comes with downriggers and everything else you need for a productive day on the water. There’s a toilet on board for your convenience. Rods, reels, and tackle are ready for you, as well as lures.
Trips are run with the help of a First Mate. A 15–20% tip is customary to show your appreciation for their hard work.
Before coming aboard, you may need to buy a local fishing license for everyone in your group. There are all licenses and stamps necessary and available for purchase aboard the boat for your convenience.
Don’t leave home without bottled water, sunglasses, and sunscreen (non-spray). Alcohol is allowed in moderation, but you should avoid hard liquor as well as glass bottles. Make sure to bring a cooler along to bring home your catch!
Now, it’s time to hit the water with Playin’ Hooky Sportfishing Charters!
Customer reviews
Rating summary
Photos & videos by reviewers (19)
+16Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Jul 14, 2025
Half Day Trip (AM)
Excellent First Experience
We had an unforgettable morning with Playin Hookey Sport Fishing Charters out of Sheboygan! My wife, our two kids (ages 10 and 4), and I went out on a 5-hour charter with Tony and Jake — and it was a fantastic experience from start to finish. These guys were incredibly knowledgeable, patient, and great with the kids. We caught some beautiful salmon and trout, and the crew made it fun and exciting the entire time. The boat was super comfortable, the equipment was top-notch, and everything was clearly well-maintained. Whether you’re an experienced angler or going out for the first time, you won’t regret choosing Captain Dave and his crew. Highly recommended — we’ll definitely be back! - Garett from Iowa
We had an unforgettable morning with Playin Hookey Sport Fishing Charters out of Sheboygan! My wife, our two kids (ages 10 and...
Jun 28, 2025
Half Day Trip (AM)
Tough day on the water
Today was a very tough bite for us. We did manage to net 2 fish. A decent steelhead and a big lake trout. My daughter got the steelhead and my nephew got the laker. We did have 4 other bites and lost those fish. Captain Tony and his deckhand were amazing. My oldest brother fished with us as well and he is in a wheelchair. With the help of the Captain and other teammates from this charter we were able to load him in the boat. Thank you guys for a memorable trip. The lake trout is my nephews largest fish to date. I would highly recommend these guys. Good luck fishing and hopefully we see you again in the future. God bless.
Today was a very tough bite for us. We did manage to net 2 fish. A decent steelhead and a big lake trout. My daughter got the...
Captain replied
May 24, 2025
Evening Mini Charter
Beautiful evening even though fish weren’t biting
It was beautiful evening for our charter! The captain and first mate were great! Very friendly! We were hopeful for fish, it only got 1 coho salmon. From the sounds of it not many other boats had fish biting either! It was still a beautiful being on the water, having conversations with the captain and first mate. We can’t control the fish, but they helped to still make it an enjoyable experience. They were very nice with our children too (ages 12, 10 and 9). I’d definitely go back on their charter again! Next time, we will do the morning charters (sound alike that’s when more fish are biting!)
It was beautiful evening for our charter! The captain and first mate were great! Very friendly! We were hopeful for fish, it...
Captain replied
Jun 29, 2025
Evening Mini Charter
Knowledgeable and Friendly Crew
Captain Tony and Jake were good hangs in addition to being extremely knowledgeable. We had a weird weather day on the boat with most of our time between two storm fronts, but Jake and Tony made everyone comfortable and answered all of our questions about weather and lakes and fish. In particular, huge shout out to first-mate Jake who took our two kids, 11 and 9, under wing. Would highly recommend Playing Hooky, and while I'm sure everyone on staff is great, you def want Tony and Jake! :)
Captain Tony and Jake were good hangs in addition to being extremely knowledgeable. We had a weird weather day on the boat with...
Jul 5, 2025
Half Day Trip (PM)
Great Trip
We had a great captain and mate that put us on fish almost immediately. Decided to go in a little early because of rough water, but will book with them again.
We had a great captain and mate that put us on fish almost immediately. Decided to go in a little early because of rough water,...
Captain repliedTrip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (19)
+16Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Experience:
Boat
Crew
Overall
Excellent First Experience
Half Day Trip (AM) on July 14, 2025
We had an unforgettable morning with Playin Hookey Sport Fishing Charters out of Sheboygan! My wife, our two kids (ages 10 and 4), and I went out on a 5-hour charter with Tony and Jake — and it was a fantastic experience from start to finish. These guys were incredibly knowledgeable, patient, and great with the kids. We caught some beautiful salmon and trout, and the crew made it fun and exciting the entire time. The boat was super comfortable, the equipment was top-notch, and everything was clearly well-maintained. Whether you’re an experienced angler or going out for the first time, you won’t regret choosing Captain Dave and his crew. Highly recommended — we’ll definitely be back! - Garett from Iowa
We had an unforgettable morning with Playin Hookey Sport Fishing Charters out of Sheboygan! My wife, our two kids (ages 10 and 4), and I went out on a 5-hour charter with Tony and Jake — and it was a fantastic experience from start to finish. These guys were incredibly knowledgeable, patient, and great with the kids. We caught some beautiful salmon and trout, and the crew made it fun and exciting the entire time. The boat was super comfortable, the equipment was top-notch, and everything was...
Experience:
Boat
Crew
Overall
Tough day on the water
Half Day Trip (AM) on June 28, 2025
Today was a very tough bite for us. We did manage to net 2 fish. A decent steelhead and a big lake trout. My daughter got the steelhead and my nephew got the laker. We did have 4 other bites and lost those fish. Captain Tony and his deckhand were amazing. My oldest brother fished with us as well and he is in a wheelchair. With the help of the Captain and other teammates from this charter we were able to load him in the boat. Thank you guys for a memorable trip. The lake trout is my nephews largest fish to date. I would highly recommend these guys. Good luck fishing and hopefully we see you again in the future. God bless.
Today was a very tough bite for us. We did manage to net 2 fish. A decent steelhead and a big lake trout. My daughter got the steelhead and my nephew got the laker. We did have 4 other bites and lost those fish. Captain Tony and his deckhand were amazing. My oldest brother fished with us as well and he is in a wheelchair. With the help of the Captain and other teammates from this charter we were able to load him in the boat. Thank you guys for a memorable trip. The lake trout is my nephews largest...
Experience:
Boat
Crew
Overall
Beautiful evening even though fish weren’t biting
Evening Mini Charter on May 24, 2025
It was beautiful evening for our charter! The captain and first mate were great! Very friendly! We were hopeful for fish, it only got 1 coho salmon. From the sounds of it not many other boats had fish biting either! It was still a beautiful being on the water, having conversations with the captain and first mate. We can’t control the fish, but they helped to still make it an enjoyable experience. They were very nice with our children too (ages 12, 10 and 9). I’d definitely go back on their charter again! Next time, we will do the morning charters (sound alike that’s when more fish are biting!)
It was beautiful evening for our charter! The captain and first mate were great! Very friendly! We were hopeful for fish, it only got 1 coho salmon. From the sounds of it not many other boats had fish biting either! It was still a beautiful being on the water, having conversations with the captain and first mate. We can’t control the fish, but they helped to still make it an enjoyable experience. They were very nice with our children too (ages 12, 10 and 9). I’d definitely go back on their...
Experience:
Boat
Crew
Overall
Knowledgeable and Friendly Crew
Evening Mini Charter on June 29, 2025
Captain Tony and Jake were good hangs in addition to being extremely knowledgeable. We had a weird weather day on the boat with most of our time between two storm fronts, but Jake and Tony made everyone comfortable and answered all of our questions about weather and lakes and fish. In particular, huge shout out to first-mate Jake who took our two kids, 11 and 9, under wing. Would highly recommend Playing Hooky, and while I'm sure everyone on staff is great, you def want Tony and Jake! :)
Captain Tony and Jake were good hangs in addition to being extremely knowledgeable. We had a weird weather day on the boat with most of our time between two storm fronts, but Jake and Tony made everyone comfortable and answered all of our questions about weather and lakes and fish. In particular, huge shout out to first-mate Jake who took our two kids, 11 and 9, under wing. Would highly recommend Playing Hooky, and while I'm sure everyone on staff is great, you def want Tony and Jake! :)
Experience:
Boat
Crew
Overall
Great Trip
Half Day Trip (PM) on July 5, 2025
We had a great captain and mate that put us on fish almost immediately. Decided to go in a little early because of rough water, but will book with them again.
We had a great captain and mate that put us on fish almost immediately. Decided to go in a little early because of rough water, but will book with them again.
FAQs about Playin' Hooky Sportfishing Charters
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