Playin Hooky 

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

Playin Hooky 

5.0/5 (12 reviews)
map-thumbnail
525 Newport Drive
Naples, FL, United States

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.

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Customer reviews

Rating summary

5.0/5
out of 5 stars from 12 reviews
Boat
4.9/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (26)

Captain Dave
Captain Dave
Captain Dave
+23

Angler rating

10
0
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

75%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

83%

Caught fish

90%

Showing 1 - 5 of 12 reviews
Showing: 5 of 12 reviews
Bart R.
Bart R.
5.0/5

May 8, 2025

Bowfishing - Stingrays and Sharks!

Fishing with Dave

VERIFIED

 

 Bart R. recommends Playin Hooky
 Bart R. recommends Playin Hooky

Sarah N.
Sarah N.
5.0/5

Mar 26, 2024

8 Hour Trip – 10k Islands inshore

Day out with the Boys

VERIFIED

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!

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...  

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+4
Captain replied
 Sarah N. recommends Playin Hooky
 Sarah N. recommends Playin Hooky
undefined (The Captain)
Replied on March 27, 2024
Thank you Sarah! Had a blast with you and the boys, let me know when you are wanting to do Pythons!

Camryn C.
Camryn C.
5.0/5

Apr 7, 2024

4 Hour Trip – Backwater 10k Islands

Captain Dave

VERIFIED

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!

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...  

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Captain replied
 Camryn C. recommends Playin Hooky
 Camryn C. recommends Playin Hooky
undefined (The Captain)
Replied on April 8, 2024
Thank you so much Camryn! Had a great day and I'm looking forward to your next trip with the stingrays!

Tom M.
Tom M.

Feb 27, 2025

The captain canceled

VERIFIED

The charter operator canceled on trip date. This is an automated posting.

 


Ryan C.
Ryan C.
5.0/5

Mar 29, 2023

4 Hour Trip – Backwater 10k Islands

We had a great time!

VERIFIED

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!

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...  

Captain replied
 Ryan C. recommends Playin Hooky
 Ryan C. recommends Playin Hooky
undefined (The Captain)
Replied on March 30, 2023
Thank you Ryan! It was great to spend the afternoon with you. Looking forward to our next trip!

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
November 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Fish Fry Special!
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
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US $450 
Entire boat: up to 3 people
4 Hour Trip – Backwater 10k Islands
FREE Cancellation 3 days notice
4 Hour Trip, starts at 9:00 AM
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US $550 
Entire boat: up to 3 people
4 Hour Trip - SHARKS!!!
FREE Cancellation 3 days notice
4 Hour Trip, starts at 9:00 AM
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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
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US $600 
Entire boat: up to 3 people
8 hour - Near Shore Wreck Fishing
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
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US $900 
Entire boat: up to 3 people
8 Hour Trip – 10k Islands inshore
FREE Cancellation 3 days notice
8 Hour Trip, starts at 8:00 AM
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US $900 
Entire boat: up to 3 people

Customer reviews

Rating summary

5.0/5
out of 5 stars from 12 reviews
Boat
4.9/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (26)

Captain Dave
Captain Dave
Captain Dave
+23

Angler rating

10
0
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

75%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

83%

Caught fish

90%

Showing 1 - 5 of 12 reviews
Showing: 5 of 12 reviews
Bart R.
Bart R.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Fishing with Dave

VERIFIED

Bowfishing - Stingrays and Sharks! on May 8, 2025

 

 Bart R. recommends Playin Hooky

Sarah N.
Sarah N.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Day out with the Boys

VERIFIED

8 Hour Trip – 10k Islands inshore on March 26, 2024

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!

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!  

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+4
 Sarah N. recommends Playin Hooky
undefined (The Captain)
Replied on March 27, 2024
Thank you Sarah! Had a blast with you and the boys, let me know when you are wanting to do Pythons!

Camryn C.
Camryn C.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Captain Dave

VERIFIED

4 Hour Trip – Backwater 10k Islands on April 7, 2024

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!

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!  

Review media 0
Review media 1
Review media 0
Review media 1
 Camryn C. recommends Playin Hooky
undefined (The Captain)
Replied on April 8, 2024
Thank you so much Camryn! Had a great day and I'm looking forward to your next trip with the stingrays!

Tom M.
Tom M.

The captain canceled

VERIFIED

Trip was supposed to happen on February 27, 2025

The charter operator canceled on trip date. This is an automated posting.

 


Ryan C.
Ryan C.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

We had a great time!

VERIFIED

4 Hour Trip – Backwater 10k Islands on March 29, 2023

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!

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!  

 Ryan C. recommends Playin Hooky
undefined (The Captain)
Replied on March 30, 2023
Thank you Ryan! It was great to spend the afternoon with you. Looking forward to our next trip!

FAQs about Playin Hooky

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The fish you can target

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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
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