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Guides > Captain Dave Roberts

Playin Hooky Fishing Charter

Naples FL

Playin Hooky Fishing Charter
Playin Hooky Fishing Charter
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Guidesly Guarantee

Excellent

(9 reviews)

5

Your Captain

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Dave Roberts

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Guides > Captain Dave Roberts

Playin Hooky Fishing Charter

locationNaples FL

Guidesly Guarantee
5 9 reviews

Your Captain

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Dave Roberts

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Dave Roberts, Captain at Playin Hooky Fishing Charter

Embark on an unforgettable fishing expedition in the beautiful waters of Naples with Playin Hooky, led by the experienced and dedicated Captain Dave. With his extensive expertise and deep-rooted love for fishing, Captain Dave is well-equipped to guide you through an exciting adventure on the water. His years of experience have allowed him to master the intricacies of the local fishing locations, ensuring a remarkable fishing charter tailored to your desires. Whether you're a novice angler or a seasoned pro, Captain Dave's wealth of knowledge will make your time aboard Playin Hooky an exceptional experience.


Playin Hooky specializes in providing exceptional inshore fishing experiences, allowing you to explore the bountiful waters of Naples, including the flats and backcountry. Depending on weather conditions, there may also be opportunities to venture into nearshore spots and wrecks for added excitement. Captain Dave is highly skilled in a diverse range of fishing techniques, ensuring that anglers of all proficiency levels can partake in a successful and exhilarating fishing outing. Whether you prefer light tackle, heavy tackle, bottom fishing, trolling, jigging, or popping, or are eagerly anticipating the upcoming introduction of bow fishing, Playin Hooky has you covered with a comprehensive selection of techniques to suit your preferences and enhance your adventure.


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.


While weather conditions may determine the availability of nearshore spots and wrecks, there is still an exciting array of targeted species awaiting your angling skills. Prepare to encounter an impressive range of fish, including Sheepshead, Tripletail, Snook, Tarpon, Redfish, and even some larger species like Grouper, Blacktip, and Bull Shark.


Enjoy a hassle-free fishing charter with Playin Hooky. Captain Dave provides all the necessary fishing equipment and covers fishing licenses, allowing you to focus on the thrill of fishing. Complimentary drinks, meals, and snacks are included, but feel free to bring your own. Captain Dave lets you keep your catch and offers cleaning services.


Book your unforgettable fishing charter in Naples' year-round waters.

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Upcoming Availability

September 2025
October 2025

Expertise & Attributes

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fishing

fishing

Master GuideMaster GuideTechnical FishingTechnical FishingFly FishingFly FishingDrift FishingDrift FishingGood with New AnglersGood with New AnglersGood with FamiliesGood with FamiliesGood with KidsGood with KidsNature / Wildlife ViewsNature / Wildlife ViewsSaltwater FishingSaltwater FishingFreshwater FishingFreshwater FishingLive BaitLive Bait

Fishing Techniques

JiggingTrolling FishingBow FishingHeavy TackleLight TackleDeep Sea / Bottom Fishing

What's Included

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Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

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Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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License

License

Read about the licensing details that is / is not covered in the below trips.

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Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

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Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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What's Included

Keep your Catch

Keep your Catch

This guide offers trips that you are able to take home your catch.

Show More

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

Show More

License

License

Read about the licensing details that is / is not covered in the below trips.

Show More

Nature / Wildlife Views

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Show More

Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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Trips Available with Playin Hooky Fishing Charter

4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea Trout
Best Price Guarantee
4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea TroutTop-Rated
4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea TroutInstant Booking
4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea TroutFishing - Flats
4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea Trout

Playin Hooky20'Lowe Max 3 guests (base trip price includes 3 guests)

4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea Trout

Join Playin' Hooky Fishing Charter for a focused 4-hour trip through Naples’ iconic 10,000 Islands flats. This guided trip is ideal for anglers of all skill levels and targets species such as Black Drum, Sea Trout, Sheepshead, Snook, and Tarpon. The outing begins from our 20' Lowe vessel, accommodating up to six guests, with the base price covering two. Guests will navigate serene backwaters, flats, and, weather permitting, nearshore wrecks, while our experienced crew provides guidance, bait, tackle, and equipment. This trip emphasizes hands-on fishing experience, opportunities for multiple catches, and safe, educational instruction designed for both beginners and seasoned anglers.

Morning Trip

4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea TroutMaximum 3 persons allowed
(base trip price includes 3 guests)
4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea Trout4 Hours
4-Hour Flats Fishing Charter in Naples, FL Targeting Black Drum and Sea Trout9:00 AM
$450

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Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks
Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksTop-Rated
Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksInstant Booking
Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksFishing - Inshore
Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks

Playin Hooky20'Lowe Max 3 guests (base trip price includes 3 guests)

Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks

Join Playin' Hooky Fishing Charter for a 4-hour inshore trip in Naples, FL, focused on landing Bull Sharks and Blacktip Sharks. This guided outing is suitable for anglers with all skill levels and includes full use of fishing gear, bait, and required licenses. Departing at 9:00 AM, guests will navigate productive inshore waters known for these apex predators. The trip emphasizes hands-on shark fishing techniques, multiple catch opportunities, and safety instruction from our experienced crew. Bring snacks and drinks, and enjoy a structured, engaging experience designed for thrill-seekers and first-time shark anglers alike, all on our well-equipped vessel.

Morning Trip

Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksMaximum 3 persons allowed
(base trip price includes 3 guests)
Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks4 Hours
Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks9:00 AM
$650

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Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks
Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksTop-Rated
Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksInstant Booking
Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksFishing - Inshore
Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks

Playin Hooky20'Lowe Max 3 guests (base trip price includes 3 guests)

Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks

Experience Playin' Hooky Fishing Charter’s 4-hour evening inshore fishing trip in Naples, FL, designed to target Bull Sharks and Blacktip Sharks as the sun sets over the Gulf of Mexico. This guided trip is suitable for all skill levels and includes high-quality fishing gear, bait, and required licenses. Guests will explore both open ocean and backwater areas, with the chance to encounter Goliath Grouper and other notable species along the way. The outing emphasizes hands-on shark fishing techniques, safety instruction, and multiple catch opportunities while providing a structured, engaging experience. Bring snacks and drinks to enjoy a night on the water focused on action and skill development in a safe, well-equipped vessel.

Evening Trip

Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip SharksMaximum 3 persons allowed
(base trip price includes 3 guests)
Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks4 Hours
Evening Inshore Shark Fishing Charter in Naples, FL Targeting Bull and Blacktip Sharks6:00 PM
$750

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Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip Sharks
Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip SharksTop-Rated
Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip SharksInstant Booking
Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip SharksFishing - Inshore
Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip Sharks

Playin Hooky20'Lowe Max 3 guests (base trip price includes 3 guests)

Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip Sharks

Join Playin' Hooky Fishing Charter for a 4-hour inshore bowfishing trip in Naples, FL, where guests begin by targeting Stingrays to use as live bait for Bull Sharks and Blacktip Sharks. This guided trip accommodates anglers of all skill levels and includes top-quality fishing gear, bait, and necessary licenses. Participants may also catch agile Barndoor Skate along the way, adding variety to the experience. Unused Stingrays can be taken home as a scallop-like treat. The outing emphasizes hands-on bowfishing techniques, safety instruction, and multiple catch opportunities, all on a well-equipped vessel designed for inshore adventures in productive local waters.

Evening Trip

Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip SharksMaximum 3 persons allowed
(base trip price includes 3 guests)
Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip Sharks4 Hours
Inshore Bowfishing Charter in Naples, FL Targeting Bull and Blacktip Sharks6:00 PM
$750

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Private Python Hunting Guided Trip in South Florida
Private Python Hunting Guided Trip in South FloridaTop-Rated
Private Python Hunting Guided Trip in South FloridaInstant Booking
Private Python Hunting Guided Trip in South FloridaHunting - Active hunting

Private Python Hunting Guided Trip in South Florida

Join Amy Siewe, The Python Huntress, for a 5-hour private hunting trip in South Florida focused on tracking and capturing invasive Burmese pythons. This guided experience is suitable for hunters of all skill levels and includes hands-on instruction, expert tips, and strategies for safely locating and handling these large snakes. The trip begins at designated summer hotspots, where participants hunt from the Snake Deck at the back of Amy’s truck, gaining access to prime python territory. All necessary equipment and guidance are provided, ensuring a safe, educational, and engaging adventure while developing your hunting skills in a controlled, structured environment.

Evening Trip

Private Python Hunting Guided Trip in South FloridaMaximum 4 persons allowed
(base trip price includes 4 guests)
Private Python Hunting Guided Trip in South Florida5 Hours
Private Python Hunting Guided Trip in South Florida8:00 PM
$1,500

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Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and Cobia
Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and CobiaTop-Rated
Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and CobiaInstant Booking
Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and CobiaFishing - Wrecks
Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and Cobia

Playin Hooky20'Lowe Max 3 guests (base trip price includes 3 guests)

Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and Cobia

Join Playin' Hooky Fishing Charter for an 8-hour nearshore wreck fishing trip in Naples, FL, designed for anglers of all skill levels. The trip begins by collecting fresh bait from our traps before heading to a productive wreck just three miles offshore, keeping land in sight. Guests will target species including Black Drum, Cobia, Permit, Snook, Tarpon, Redfish, Spotted Seatrout, Tripletail, Sheepshead, and more. The outing includes all necessary fishing gear, bait, and licenses, allowing anglers to focus on hands-on techniques, multiple catch opportunities, and learning from experienced guides. With ample time to explore this nearshore hotspot, participants can enjoy a structured, safe, and engaging fishing experience on a well-equipped vessel.

Full Day Trip

Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and CobiaMaximum 3 persons allowed
(base trip price includes 3 guests)
Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and Cobia8 Hours
Nearshore Wreck Fishing Charter in Naples, FL Targeting Black Drum and Cobia8:00 AM
$850

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Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack Crevalle
Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack CrevalleTop-Rated
Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack CrevalleInstant Booking
Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack CrevalleFishing - Inshore
Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack Crevalle

Playin Hooky20'Lowe Max 3 guests (base trip price includes 3 guests)

Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack Crevalle

Experience Playin' Hooky Fishing Charter’s 8-hour inshore fishing trip in Naples, FL, departing at 8:00 AM to explore the backwaters of the 10,000 Islands. This guided trip is suitable for anglers of all skill levels and includes all fishing gear, bait, and licenses. Guests will target a variety of species including Black Drum, Jack Crevalle, Goliath Grouper, Snook, Tarpon, Mangrove Snapper, Redfish, Ladyfish, Spanish Mackerel, Spotted Seatrout, Flounder, and Sheepshead. Depending on conditions, the trip may also include nearshore wreck fishing to diversify the experience. The outing emphasizes hands-on instruction, multiple catch opportunities, and safe, structured guidance while navigating productive inshore and nearshore waters, all on a well-equipped vessel designed for full-day excursions.

Full Day Trip

Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack CrevalleMaximum 3 persons allowed
(base trip price includes 3 guests)
Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack Crevalle8 Hours
Inshore Fishing Charter in Naples, FL Targeting Black Drum and Jack Crevalle8:00 AM
$850

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Vehicle

Playin Hooky

Boat Type:

Boat Guest Capacity:

3

Boat Length:

20 ft

Manufacturer Name:

Lowe

Model Year:

2018

Engine Manufacturer Name:

Mercury

# of Engines:

1

Horsepower Per Engine:

115

Maximum Cruising Speed:

38

Features: Bait Tank Ice-Box Trolling Motor Fish Finder GPS

Playin Hooky Fishing Charter Lowe Boat

The 20-foot Lowe boat features spacious casting decks at the front and rear, perfect for anglers who love to cast. It also includes a bait well and a large 60-gallon livewell, ideal for culling slot fish.

Boat

Playin Hooky Fishing Charter Lowe Boat image 0

Playin Hooky

Boat Type:

Boat Guest Capacity:

3

Boat Length:

20 ft

Vehicle Details

FAQs about Playin Hooky Fishing Charter

Reports and Expert Articles

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Secondary Title: Stingray Bowfishing – Catch Your Bait, Enjoy Scallop-Like Delights for Dinner!

Sing ray bow fishing! Imitation scallops for dinner!

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Naples Fishing Trip

We had a fantastic fishing trip with Naples Fishing Charter. We successfully caught several sheepshead and black drum. Everyone was thoroughly impressed and delighted with the experience.

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Fishing Charters Naples FL - Ten Thousand Islands Backcountry Fishing

Summer fishing is on fire! The trout are massive, giving anglers some exciting battles. Spanish mackerel have arrived, adding even more action to the waters. And if that's not enough, big reds are lurking nearby, promising heart-pounding encounters. Don't miss out on this incredible fishing opportunity—grab your gear and head out for a memorable day on the water!

Ratings & Reviews Summary

5.00
out of 5
Based on 9 ratings
100%
recommended
recommended
Based on 9 recommendations
5
9
4
3
2
1

September 6, 2025

We're thrilled with our decision to book this trip! Dave expertly located the fish and showcased his deep knowledge of the region. We managed to catch different types of fish, including an impressively sized bull shark. The communication during the booking was excellent. Strongly recommended!

September 6, 2025

The captain demonstrated exceptional expertise in navigating the waters and ensured an ample supply of water and Gatorade. If fishing proves unproductive, he actively seeks alternative catches and tirelessly explores numerous locations, never relenting in his efforts.

September 6, 2025

This guy knows and loves fishing. Had a great time, catching many different species in the 10,000 Islands. Off the top of my head I remember catching, snook, reddish, mangrove snapper, Bonita, mackerel, and a pretty small Goliath grouper, along others. I'll definitely be contacting Dave again. Maybe next time I'll be able to bring in a full grown Goliath and/or a shark! If you find yourself in Southwest Florida looking for a charter, book with Playin' Hooky.

September 6, 2025

If you want to catch fish and lots of them, Dave is your guy! We hit 10 different spots and with in the first or second cast we were catching fish at each locations. His passion and knowledge of fishing around the islands was shown through out the day as we fished. It didn’t matter if we fished with live or artificial baits and caught fish! His professionalism was top notch and I plan on booking again soon.

September 6, 2025

Wow, PHFC took us out last year and it was insane! Caught some massive snook and had a blast. Can't wait to go again!

September 6, 2025

Had an awesome trip with Playin' Hooky last summer. The captain was super knowledgeable and put us on the fish right away. Highly recommend!

Captain Fishing Species

Barndoor Skate

Species Name: Dipturus Laevis

Habitat: Onshore, Offshore, Ocean Floor, Continental Shelves

Weight: 4 - 44 lbs.

Black Drum

Species Name: Pogonias Cromis

Habitat: Brackish Waters, Onshore

Weight: 15 - 90 lbs.

Blacktip Shark

Species Name: Carcharhinus Limbatus

Habitat: Onshore, Nearshore, Continental Shelves, Insular Shelves

Weight: 100 - 150 lbs.

Bull Shark

Species Name: Carcharhinus Leucas

Habitat: Warm, Shallow Nearshore, River

Weight: 200 - 500 lbs.

Cobia

Species Name: Rachycentron Canadum

Habitat: Onshore, Nearshore, Offshore, Reef, Wreck

Weight: 10 - 80 lbs.

Crevalle Jack

Species Name: Caranx Hippos

Habitat: River, Onshore, Nearshore, Offshore, Reef, Flats Backcountry, Wreck

Weight: 15 - 60 lbs.

Goliath Grouper

Species Name: Epinephelus Itajara

Habitat: Onshore, Nearshore, Reef, Backcountry, Flats, Wreck

Weight: 75 - 150 lbs.

Permit

Species Name: Trachinotus Falcatus

Habitat: Inshore, Flats, Offshore, Reefs, Jetties

Weight: 9 - 60 lbs.

Redfish

Species Name: Sciaenops Ocellatus

Habitat: Onshore, Flats, Backcountry, Nearshore

Weight: 10 - 45 lbs.

Sea Trout

Species Name: Salmo Trutta

Habitat: Inshore, Nearshore, Covered River

Weight: 1 - 6 lbs.

Sheepshead

Species Name: Archosargus Probatocephalus

Habitat: Onshore, Nearshore, Offshore, Reef, Wreck

Weight: 1 - 8 lbs.

Snook

Species Name: Centropomus Undecimalis

Habitat: Inshore, Flats, Backcountry

Weight: 12 - 29 lbs.

Spanish Mackerel

Species Name: Scomberomorus Maculatus

Habitat: offshore, onshore, nearshore

Weight: 8 - 120 lbs.

Tarpon

Species Name: Megalops Atlanticus

Habitat: Inshore, Flats, Backcountry

Weight: 25 - 63 lbs.

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