Playin' Hooky Sportfishing Charters
4.9/5 (15 reviews)
641 Riverfront Drive, Sheboygan, WI 53081, United States–
Playin' Hooky Sportfishing Charters
4.9/5 (15 reviews)
641 Riverfront Drive
Sheboygan, WI, United States
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
Boat
4.8/5
Crew
4.9/5
Experience
4.8/5
Photos & videos by reviewers (23)
+20Angler rating
13
1
0
0
0
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
93%
Caught fish
100%
Showing 1 - 5 of 15 reviews
Showing: 5 of 15 reviews
Garett Hamilton
5.0
Verified
Excellent First Experience
Half Day Trip (AM) on July 14, 2025 • 2 adults • 2 children
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
Reported Catch:
1
Raymond Krueger
5.0
Verified
Tough day on the water
Half Day Trip (AM) on June 28, 2025 • 4 adults
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.
Reported Catch:
Response from Captain
July 8, 2025
Thanks very much for fishing with us Raymond! We look forward to guiding you again in the future! Thanks for the great review.
1
Jehvana Cook
4.7
Verified
Beautiful evening even though fish weren’t biting
Evening Mini Charter on May 24, 2025 • 2 adults • 3 children
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!)
Response from Captain
May 29, 2025
Thanks for the wonderful review, Jehvana! We’re glad you enjoyed your trip even though the fish were in a negative mood for those three hours. Nature can be goofy for a couple hours at a time. We’d love to have you back any time of day! Monday night during the same time frame we ended up getting a 15 fish limit in almost no time. It really is up to Mother Nature.
We’re glad your kids had fun and we hope to see you all again soon!
Captain Dave
1
Heather Eastlund
5.0
Verified
Knowledgeable and Friendly Crew
Evening Mini Charter on June 29, 2025 • 2 adults • 2 children
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! :)
Reported Catch:
0
Jordan Tamminga
5.0
Verified
Great Trip
Half Day Trip (PM) on July 5, 2025 • 4 adults
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.
Reported Catch:
Response from Captain
July 6, 2025
Thank you very much for fishing with us yesterday, Jordan! We’re glad we were able to get you some nice fish before we had to go in. Can’t wait to fish with you again!
0
Trip availability and prices
Trip Date:
Days:
Group Size:
Select date to see availability
October 2025
| Su | Mo | Tu | We | Th | Fr | Sa | |
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Number of days
1
Group Size
2 adults • 0 children
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Evening Mini Charter
Low rate deposit non-refundable
3 Hour Trip, starts at 5:00 PM
Seasonal trip May 1 - Oct 1
US $507
Entire boat: up to 6 people
Half Day Trip (AM)
Low rate deposit non-refundable
5 Hour Trip, starts at 5:00 AM
Seasonal trip May 1 - Oct 1
US $655
Entire boat: up to 6 people
Half Day Trip (Midday)
Low rate deposit non-refundable
5 Hour Trip, starts at 10:00 AM
Seasonal trip May 1 - Oct 10
US $655
Entire boat: up to 6 people
Half Day Trip (PM)
Low rate deposit non-refundable
5 Hour Trip, starts at 3:30 PM
Seasonal trip May 1 - Oct 10
US $689
Entire boat: up to 6 people
There are 2 people looking at this charter.
Customer reviews
Rating summary
Boat
4.8/5
Crew
4.9/5
Experience
4.8/5
Photos & videos by reviewers (23)
+20Angler rating
13
1
0
0
0
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
93%
Caught fish
100%
Showing 1 - 5 of 15 reviews
Showing: 5 of 15 reviews
Garett Hamilton
5.0
Verified
Excellent First Experience
Half Day Trip (AM) on July 14, 2025 • 2 adults • 2 children
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
Reported Catch:
1
Raymond Krueger
5.0
Verified
Tough day on the water
Half Day Trip (AM) on June 28, 2025 • 4 adults
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.
Reported Catch:
Response from Captain
July 8, 2025
Thanks very much for fishing with us Raymond! We look forward to guiding you again in the future! Thanks for the great review.
1
Jehvana Cook
4.7
Verified
Beautiful evening even though fish weren’t biting
Evening Mini Charter on May 24, 2025 • 2 adults • 3 children
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!)
Response from Captain
May 29, 2025
Thanks for the wonderful review, Jehvana! We’re glad you enjoyed your trip even though the fish were in a negative mood for those three hours. Nature can be goofy for a couple hours at a time. We’d love to have you back any time of day! Monday night during the same time frame we ended up getting a 15 fish limit in almost no time. It really is up to Mother Nature.
We’re glad your kids had fun and we hope to see you all again soon!
Captain Dave
1
Heather Eastlund
5.0
Verified
Knowledgeable and Friendly Crew
Evening Mini Charter on June 29, 2025 • 2 adults • 2 children
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! :)
Reported Catch:
0
Jordan Tamminga
5.0
Verified
Great Trip
Half Day Trip (PM) on July 5, 2025 • 4 adults
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.
Reported Catch:
Response from Captain
July 6, 2025
Thank you very much for fishing with us yesterday, Jordan! We’re glad we were able to get you some nice fish before we had to go in. Can’t wait to fish with you again!
0
FAQs about Playin' Hooky Sportfishing Charters
The fish you can target
What is the boat like?
Boat category
Sportfishing boatsCapacity
6 personsBoat length
36 ftYear built
1985Boat manufacturer
Chris-CraftBoat type
SportfishingEngine model
MercuryPowered by
2 x 350HPMax cruising speed
25 knots