Playin' Hooky Sportfishing Charters 

4.9
(22 reviews)
 641 Riverfront Drive, Sheboygan, WI 53081, United States

Playin' Hooky Sportfishing Charters 

Sheboygan, WI, United States
36 ft
6
4.9
(22 reviews)

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!

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!

Playin' Hooky Sportfishing Charters
Charter Operator
Playin' Hooky Sportfishing Charters
19 years of experience
ID & credentials verified
responds within an hour

Select date to see availability

Trip availability and prices

Trip date:
Group Size:
September 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
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Evening Mini Charter
Non-refundable
3 hour trip starts at 5:00 PM
Seasonal trip
May 1 - Oct 1
Lake Trout
Rainbow Trout (Steelhead)
Brown Trout
Salmon (Chinook)
+1
US $507
Entire boat: up to 3 people
Half Day Trip (AM)
Non-refundable
5 hour trip starts at 5:00 AM
Seasonal trip
May 1 - Oct 1
Lake Trout
Rainbow Trout (Steelhead)
Brown Trout
Salmon (Chinook)
+1
US $655
Entire boat: up to 3 people
Half Day Trip (Midday)
In high demand Last booked: 1 day ago
Non-refundable
5 hour trip starts at 10:00 AM
Seasonal trip
May 1 - Oct 10
Lake Trout
Rainbow Trout (Steelhead)
Brown Trout
Salmon (Chinook)
+1
US $655
Entire boat: up to 3 people
Half Day Trip (PM)
Non-refundable
5 hour trip starts at 3:30 PM
Seasonal trip
May 1 - Oct 10
Lake Trout
Rainbow Trout (Steelhead)
Brown Trout
Salmon (Chinook)
+1
US $689
Entire boat: 2 people
There are 12 people looking at this charter.

Customer reviews

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Rating

4.9
22 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (35)

All reviews (22)

Frequently mentioned
Showing 15 of 22 reviews
Stephen Brady
Stephen Brady
us
Pennsylvania, US
Member since 2026
5.0
Verified
New
Great fishing trip!
Half Day Trip (AM) on August 24, 20262 adults

J ust wanted to say thank you for a great trip on the Happy Hooker this past Sunday morning! I really appreciated the attention Jake gave me as first mate, and Ryan did an exceptional job navigating the choppy seas. It was also a pleasure meeting John, a great gentleman. I brought home 2 coho salmon and a brown trout, froze them, and cooked some of them up last night for dinner - they were great! Thanks again to you guys for a great time. PS - my banana was my lucky charm

Reported catch:
Coho Salmon
Brown Trout
Patrick Riepe
Patrick Riepe
us
Iowa, US
Member since 2026
5.0
Verified
Nice haul of rainbow trout
Evening Mini Charter on July 11, 20261 adult2 children

Dad and twin 13-year-old boys took the Gilligan tour (three hours) and went four-for-four, landing four beautiful rainbow trout, about 8-10 pounds on average. Captain Mitch and First Mate Tom were very knowledgeable, patient, and friendly. Fish cleaned, filleted and frozen at The Wharf where we’ll pick it up for the trip home. The evening clientele at Parker John’s were in awe as we hauled our catch off the Sea Dog 2! Highly recommend.

Reported catch:
Rainbow Trout (Steelhead)
Playin' Hooky Sportfishing Charters
Response from Charter operator

thanks so much for fishing with us Patrick!! 👊👊👊

Thomas Lappin
Thomas Lappin
us
Michigan, US
Member since 2026
5.0
Verified
My best Lake Michigan fishing trip ever.
Half Day Trip (Midday) on July 5, 20264 adults

We caught 15 rainbows, one coho and one king. 10am 3pm fish time. Captain Mitch put us on the fish within the first hour and it was action packed for the rest of the day. First Mate Jake was working netting all the fish and setting us up for the next one. Great fishing and lots of fun with a great crew. thanks again to Captain Mitch and First Mate Jake !!!!

Reported catch:
Rainbow Trout (Steelhead)
Coho Salmon
Chinook Salmon
Playin' Hooky Sportfishing Charters
Response from Charter operator

Thanks very much for the great review, Tom! we hope to see you again some time when youre in the area!!

Peter Retzloff
Peter Retzloff
us
Wisconsin, US
Member since 2024
5.0
Verified
Great time
Half Day Trip (AM) on May 30, 20265 adults1 child

Captain and first mate were very helpful and friendly. Caught some nice fish and would recommend to anyone.

Playin' Hooky Sportfishing Charters
Response from Charter operator

thanks very much for fishing with us, Peter! hope to see you again!!

Leonard Hafner
Leonard Hafner
us
Illinois, US
Member since 2026
The captain canceled
June 21, 2026
Trip was supposed to happen on June 21, 2026

The charter operator canceled 1 days prior to the trip date. This is an automated posting.

FAQs about Playin' Hooky Sportfishing Charters

Playin' Hooky Sportfishing Charters offers the following trips to customers:
  • US $507 per group, additional US $34 per person after 3 guests - Evening Mini Charter (3 hours)
  • US $655 per group, additional US $34 per person after 3 guests - Half Day Trip (AM) (5 hours)
  • US $655 per group, additional US $34 per person after 3 guests - Half Day Trip (Midday) (5 hours)
  • US $655 per group, additional US $34 per person after 1 guest - Half Day Trip (PM) (5 hours)
When you book a trip with Playin' Hooky Sportfishing Charters, you can expect the following amenities onboard:
  • Toilet Full flushable toilet.
  • GPS
  • Fishfinder
  • Flybridge
  • Radar
Trips booked with Playin' Hooky Sportfishing Charters include:
  • Rods, reels & tackle
  • Lures
  • Catch cleaning & filleting (We fillet fish or bring them to a local business to be filleted free of charge.)
  • First mate (Works for tips)
Playin' Hooky Sportfishing Charters offers the following types of fishing:
  • Lake fishing
  • Nearshore fishing (We fish close to shore when the fish are there.)
  • Offshore fishing (We fish offshore when the fish are offshore.)
Playin' Hooky Sportfishing Charters offers the following fishing technique:
  • Trolling
Top targeted fish species with Playin' Hooky Sportfishing Charters include:
  • Brown Trout
  • Lake Trout
  • Rainbow Trout (Steelhead)
  • Salmon (Chinook)
  • Salmon (Coho)

Your operator

Playin' Hooky Sportfishing Charters
Playin' Hooky Sportfishing Charters

Sheboygan, Wisconsin, United States

3 Fishing Reports
ID & license verified
22 Customer reviews
Typical response within an hour
Member since January 2020

I began guiding because I fell in love with hearing the reel scream with a big King Salmon on the line. I wanted to share that experience with as many people as I could!

Playin' Hooky Sportfishing Charters
Playin' Hooky Sportfishing Charters
Fully verified
3
reports
22
reviews
2020
member since
~1h
response
I began guiding because I fell in love with hearing the reel scream with a big King Salmon on the line. I wanted to share that experience with as many people as I could!

The fish you can target

Brown Trout
Brown Trout
Lake Trout
Lake Trout
Rainbow Trout (Steelhead)
Rainbow Trout (Steelhead)
Chinook Salmon
Chinook Salmon
Coho Salmon
Coho Salmon
Brown Trout
Brown Trout
Lake Trout
Lake Trout
Rainbow Trout (Steelhead)
Rainbow Trout (Steelhead)
Chinook Salmon
Chinook Salmon
Coho Salmon
Coho Salmon

Real catches by this captain

  • Great fishing trip!
    Stephen B.
    Stephen B.
  • Nice haul of rainbow trout
    Patrick R.
    Patrick R.
  • My best Lake Michigan fishing trip ever.
    Thomas L.
    Thomas L.
  • June fishing trip
    Justin V.
    Justin V.
  • Big fish
    Terry H.
    Terry H.
  • Excellent First Experience
    Garett H.
    Garett H.
  • Great Trip
    Jordan T.
    Jordan T.
  • Tough day on the water
    Raymond K.
    Raymond K.
  • Beautiful evening even though fish weren’t biting
    Jehvana C.
    Jehvana C.
  • Great time fishing
    Jim B.
    Jim B.

What is the boat like?

Boat image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
36 ft
Year built
1985
Boat manufacturer
Chris-Craft
Boat type
Sportfishing
Engine model
Mercury
Powered by
2 x 350HP
Max cruising speed
25 knots

What kind of fishing will you do?

Lake Fishing
Nearshore Fishing
We fish close to shore when the fish are there.
Offshore Fishing
We fish offshore when the fish are offshore.

Which fishing techniques you can try

Trolling

Which amenities are available onboard

Toilet
Full flushable toilet.
GPS
Fishfinder
Flybridge
Radar
What's included in the trip price
Rods, reels & tackle
Lures
Catch cleaning & filleting
We fillet fish or bring them to a local business to be filleted free of charge.
First mate
Works for tips

How cancellations work

Deposit non-refundable

If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.

More details

What the listing policies are

Pickup not included

Transfer to/from departure site is not included in trip rates.

Child friendly
No age limits whatsoever. Our charters are very child-friendly. Use your own discretion as to whether or not a fishing trip is right for your child, no matter their age.
You keep catch

How you can pay

Book with 10% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 10% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

 Cash

 Visa

 Mastercard

 American Express

 Checks

When paying the remaining balance with a credit card, an additional 3.5% charge will apply.

What’s biting in Sheboygan right now

Brown TroutBrown Trout
Lake TroutLake Trout
Rainbow Trout (Steelhead)Rainbow Trout (Steelhead)
Salmon (Chinook)Salmon (Chinook)
Salmon (Coho)Salmon (Coho)

Compare similar fishing charters

Current
Playin' Hooky Sportfishing Charters
Playin' Hooky Sportfishing Charters
4.9
(22)
36 ft
Group size 1 - 6
1 - 6
Fish 1
Fish 2
+3
3 hour trip • 3 persons
US $507