Playin Hooky 

5.0/5 (12 reviews)
 525 Newport Drive, Naples, FL 34114, United States

Playin Hooky 

Naples, FL, United States
20 ft
3
5.0/5 (12 reviews)

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Spend an unforgettable day on the waters of Naples with Playin Hooky! Captain Dave has years of experience to share and he's happy to pass on his best tips and tricks to you. Whether you're just taking a rod for the first time or you already have a few fish trophies under your belt, you'll enjoy your time spent on this boat.

You'll be fishing on a 20' Lowe that accommodates up to 3 guests. This bay boat is powered by a 115 HP Mercury engine and reaches the speed of 38 knots, so you'll be on your fishing spot in no time. And for the moments when you need to move quietly but not fast, there's a wireless trolling engine that will let you sneak up on fish.

You'll mostly explore inshore waters, flats, and the backcountry. Nearshore spots and wrecks are also an option but they are weather-dependent. Target Sheepshead, Tripletail, Snook, Tarpon, Redfish, and some larger species, such as Grouper, Blacktip, and Bull Shark. There's also a variety of fishing techniques you can try on, with bow fishing coming soon as well.

Capt. Dave lets you keep the catch and he even cleans it after the trip free of charge. He'll also cover your fishing licenses and equipment, so you only need to pack some food, drinks, and sun protection for the day.

Playin Hooky runs trips all year long. It's always a good time for some fishing action. You only need to choose when you're coming.

Spend an unforgettable day on the waters of Naples with Playin Hooky! Captain Dave has years of experience to share and he's happy to pass on his best tips and tricks to you. Whether you're just taking a rod for the first time or you already have a few fish trophies under your belt, you'll enjoy your time spent on this boat.

You'll be fishing on a 20' Lowe that accommodates up to 3 guests. This bay boat is powered by a 115 HP Mercury engine and reaches the speed of 38 knots, so you'll be on your fishing spot in no time. And for the moments when you need to move quietly but not fast, there's a wireless trolling engine that will let you sneak up on fish.

You'll mostly explore inshore waters, flats, and the backcountry. Nearshore spots and wrecks are also an option but they are weather-dependent. Target Sheepshead, Tripletail, Snook, Tarpon, Redfish, and some larger species, such as Grouper, Blacktip, and Bull Shark. There's also a variety of fishing techniques you can try on, with bow fishing coming soon as well.

Capt. Dave lets you keep the catch and he even cleans it after the trip free of charge. He'll also cover your fishing licenses and equipment, so you only need to pack some food, drinks, and sun protection for the day.

Playin Hooky runs trips all year long. It's always a good time for some fishing action. You only need to choose when you're coming.

Dave Roberts
Captain
Dave Roberts
14 years of experience
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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Almost there...
Fish Fry Special!
FREE Cancellation 3 days notice
4 hour trip starts at 8:00 AM
Bass (Largemouth)
Bass (Peacock)
US $450
Entire boat: 2 people
4 Hour Trip – Backwater 10k Islands
FREE Cancellation 3 days notice
4 hour trip starts at 9:00 AM
Jack Crevalle
Snook
Tarpon
Snapper (Mangrove)
+6
US $550
Entire boat: 2 people
4 Hour Trip - SHARKS!!!
FREE Cancellation 3 days notice
4 hour trip starts at 9:00 AM
Grouper (Goliath)
Jack Crevalle
Shark (Blacktip)
Shark (Bull)
US $600
Entire boat: up to 3 people
Bowfishing - Stingrays and Sharks!
FREE Cancellation 3 days notice
4 hour trip starts at 6:00 PM
Shark (Blacktip)
Shark (Bull)
Skate
US $600
Entire boat: 2 people
8 hour - Near Shore Wreck Fishing
FREE Cancellation 3 days notice
8 hour trip starts at 8:00 AM
Cobia
Permit
Snook
Tarpon
+5
US $900
Entire boat: 2 people
8 Hour Trip – 10k Islands inshore
FREE Cancellation 3 days notice
8 hour trip starts at 8:00 AM
Grouper (Goliath)
Jack Crevalle
Snook
Tarpon
+8
US $900
Entire boat: 2 people
There is 1 person looking at this charter.

Customer reviews

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Rating

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

Anglers' gallery (26)

All reviews (12)

Frequently mentioned
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Showing 15 of 12 reviews
Sarah Neal
Sarah Neal
Repeat angler
us
Akron, OH, US
Member since 2023
5 trips
5.0
Verified
Day out with the Boys
8 Hour Trip – 10k Islands inshore on March 26, 20243 adults

I took my 15 year old son and his friend out. His friend has never been on a charter and we have never been on one so south in FL! Captain Dave delivered! I think we caught 10 different species around the 10K islands! Weather was windy, but Dave knew exactly where to take us to catch stuff still. Was a great time and would book with him again! Next time we might even book the snake hunting trip!

Reported catch:
Jack Crevalle
Black Drum
Redfish
Ladyfish
+3
Dave Roberts
Response from Captain

Thank you Sarah! Had a blast with you and the boys, let me know when you are wanting to do Pythons!

Camryn Caron
Camryn Caron
us
Massachusetts, US
Member since 2024
5.0
Verified
Captain Dave
4 Hour Trip – Backwater 10k Islands on April 7, 20242 adults

Dave was awesome and super knowledgeable. On a day there wasn’t much bites he kept moving until he found us a spot that hit. Will definitely call him next time we’re in Florida! Thanks Dave!

Reported catch:
Mangrove Snapper
Dave Roberts
Response from Captain

Thank you so much Camryn! Had a great day and I'm looking forward to your next trip with the stingrays!

Bart Robertson
Bart Robertson
Repeat angler
us
Texas, US
Member since 2025
7 trips
5.0
Verified
Fishing with Dave
Bowfishing - Stingrays and Sharks! on May 8, 20252 adults

Ryan Claus
Ryan Claus
us
Illinois, US
Member since 2023
5.0
Verified
We had a great time!
4 Hour Trip – Backwater 10k Islands on March 29, 20232 adults

We are so happy we booked this trip! Dave put us on the fish and is very knowledgeable about the area. We caught a variety of species and even landed a nice sized bull shark. Communication was great throughout the booking process. Highly recommend!

Dave Roberts
Response from Captain

Thank you Ryan! It was great to spend the afternoon with you. Looking forward to our next trip!

William Thuilot
William Thuilot
us
New York, US
Member since 2023
5.0
Verified
Fishing 10000 islands on playing hooky
4 Hour Trip – Backwater 10k Islands on April 12, 20231 adult2 children

The captain was excellent and very knowledgeable about the waters , he provides plenty of water and Gatorade , if the fishing is slow he finds something to catch and hits a lot of spots never gives up

Dave Roberts
Response from Captain

Thank you William!

FAQs about Playin Hooky

Playin Hooky offers the following trips to customers:
  • US $450 per group, additional US $50 per person after 2 guests - Fish Fry Special! (4 hours)
  • US $550 per group, additional US $50 per person after 2 guests - 4 Hour Trip – Backwater 10k Islands (4 hours)
  • US $600 per group - 4 Hour Trip - SHARKS!!! (4 hours)
  • US $600 per group, additional US $50 per person after 2 guests - Bowfishing - Stingrays and Sharks! (4 hours)
  • US $900 per group, additional US $50 per person after 2 guests - 8 hour - Near Shore Wreck Fishing (8 hours)
  • US $900 per group, additional US $50 per person after 2 guests - 8 Hour Trip – 10k Islands inshore (8 hours)
When you book a trip with Playin Hooky, you can expect the following amenities onboard:
  • GPS Simrad go 9xse chart plotter.
  • Fishfinder 3 in 1 transducer. Down, side, and echo scan
  • Live bait well Necessity for culling slot fish!
  • Wireless trolling motor Spot lock, we find fish, we stay on fish!
  • Ice box
Trips booked with Playin Hooky include:
  • Rods, reels & tackle
  • Live bait (Live bait includes live shrimp but not live bait fish. Bait fish can be added with 48 hours notice prior to trip. Prices vary.)
  • Lures
  • Catch cleaning & filleting (No charge for cleaning fish except the fish fry listing. ($50) All other cleaning of fish includes fillet, ziplock bags and some ice for short transportation, bring your cooler!)
  • Fishing license (Our OUPV charter fishing license includes all necessary licensing for fishing any of our packages.)
Playin Hooky offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing (Weather dependant)
  • Wreck fishing (Weather dependant)
  • Flats fishing
  • Backcountry fishing
Playin Hooky offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Bottom fishing
  • Trolling
  • Jigging
  • Popping
  • Bowfishing (Coming soon! )
Top targeted fish species with Playin Hooky include:
  • Black Drum
  • Permit
  • Pompano
  • Redfish
  • Shark (Blacktip)
  • Shark (Bull)
  • Sheepshead
  • Snapper (Mangrove)
  • Snook
  • Speckled Trout
  • Tarpon
  • Tripletail

Your captain

Dave Roberts
Dave Roberts
Dave Roberts

Naples, Florida, United States

2 Fishing Reports
12 Customer reviews
Typical response within an hour
Member since February 2021

Captain Dave has been fishing in the area for several years. His specialty are flats and inshore fishing, where he can combine all kinds of different techniques.

2 Fishing Reports
12 Customer reviews
Typical response within an hour
Member since February 2021

Captain Dave has been fishing in the area for several years. His specialty are flats and inshore fishing, where he can combine all kinds of different techniques.

The fish you can target

Black Drum
Black Drum
Permit
Permit
Pompano
Pompano
Redfish
Redfish
Blacktip Shark
Blacktip Shark
Bull Shark
Bull Shark
Sheepshead
Sheepshead
Mangrove Snapper
Mangrove Snapper
Snook
Snook
Speckled Trout
Speckled Trout
Tarpon
Tarpon
Tripletail
Tripletail
Black Drum
Black Drum
Permit
Permit
Pompano
Pompano
Redfish
Redfish
Blacktip Shark
Blacktip Shark

What is the boat like?

Boat image
Boat category
Center console boats
Capacity
3 persons
Boat length
20 ft
Year built
2018
Boat manufacturer
Lowe
Boat type
Bay boat
Engine model
Mercury
Powered by
1 x 115HP
Max cruising speed
38 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Weather dependant
Wreck Fishing
Flats Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Jigging
Popping
Bowfishing
Coming soon!

Which amenities are available onboard

GPS
Simrad go 9xse chart plotter.
Fishfinder
3 in 1 transducer. Down, side, and echo scan
Live bait well
Necessity for culling slot fish!
Wireless trolling motor
Spot lock, we find fish, we stay on fish!
Ice box

What's included in the trip price

Rods, reels & tackle
Live bait
Live bait includes live shrimp but not live bait fish. Bait fish can be added with 48 hours notice prior to trip. Prices vary.
Lures
Catch cleaning & filleting
No charge for cleaning fish except the fish fry listing. ($50) All other cleaning of fish includes fillet, ziplock bags and some ice for short transportation, bring your cooler!
Fishing license
Our OUPV charter fishing license includes all necessary licensing for fishing any of our packages.

How cancellations work

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

What the listing policies are

Pickup not included

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

Child friendly
All kids o er the age of 8 are encouraged! We have life vests and fishing equipment to accomidate!
You keep catch
Catch your dinner! Take it to local restaurant to
Catch and release allowed

How you can pay

Book with 20% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 20% 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

 PayPal

 Bank transfer

What’s biting in Naples right now

Black DrumBlack Drum
PermitPermit
PompanoPompano
RedfishRedfish
Shark (Blacktip)Shark (Blacktip)
Shark (Bull)Shark (Bull)
SheepsheadSheepshead
Snapper (Mangrove)Snapper (Mangrove)
SnookSnook
Speckled TroutSpeckled Trout
TarponTarpon
TripletailTripletail

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US $600