Next AvailableJul 01

Book with Dave Roberts

Playin Hooky Fishing Charter

5 7 reviews

Identity Verified

Naples FL

Dave Roberts, Captain at Playin Hooky Fishing Charter

Identity Verified

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.

Upcoming Availability

July 2025

August 2025

Expertise & Attributes

fishing

Drift Fishing

Fly Fishing

Freshwater Fishing

Good with Families

Good with Kids

Good with New Anglers

Live Bait

Master Guide

Nature / Wildlife Views

Saltwater Fishing

Technical Fishing

Fishing Techniques

JiggingTrolling FishingBow FishingHeavy TackleLight TackleDeep Sea / Bottom Fishing

What's Included

Keep your Catch

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

Good to Knows

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

License

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

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Cancellation Policy

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

What's Included

Keep your Catch

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

Good to Knows

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

License

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

Nature / Wildlife Views

This guide offers trips with nature and wildlife views.

Cancellation Policy

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

Trips Available with Playin Hooky Fishing Charter

Fishing

Starting At $750

Naples Fishing | 4 Hour Charter Trip

Fishing Area: Naples

Fishing: Inshore

Fishing Boat:

Playin Hooky • 20' Lowe • Max 3 guests (base trip price includes 3 guests)

Description:

Get ready for a unique 4-hour bowfishing experience that begins with targeting Stingrays, which will serve as the perfect bait for chasing after Bull and Blacktip Sharks. Along the way, you'll also have the chance to catch the agile Skate, adding variety to your fishing day. After using the Stingrays for bait, you can take home any unused ones and enjoy them as a delightful scallop-like treat. With expert guidance and top-quality equipment, you'll have all the tools you need for a successful adventure. Book now and enjoy this action-packed bowfishing experience like no other! *Deposits are non-refundable.

Fishing

Starting At $650

Fishing In Naples Florida | 4 Hour Charter Trip

Fishing Area: Naples

Fishing: Inshore

Fishing Boat:

Playin Hooky • 20' Lowe • Max 3 guests (base trip price includes 3 guests)

Description:

Get ready for a thrilling 4-hour morning fishing trip focused on targeting Bull and Blacktip Sharks, two of the most powerful and exciting predators in the area. These sharks offer an exceptional challenge for anglers looking for an unforgettable experience on the water. Captain and crew will supply all the necessary fishing gear, bait, and licenses to ensure a smooth and enjoyable day. Bring along some snacks and drinks to stay refreshed while you focus on landing your big catch. This trip begins at 9:00 AM and promises an action-packed adventure in some of the most fish-filled waters. *Deposits are non-refundable.

Fishing

Starting At $750

Naples Fishing Charters | 4 Hour Charter Trip

Fishing Area: Naples

Fishing: Inshore

Fishing Boat:

Playin Hooky • 20' Lowe • Max 3 guests (base trip price includes 3 guests)

Description:

Join us for an exciting late evening trip as we target Bull and Blacktip Sharks under the stars. As the sun sets over the Gulf of Mexico, we'll venture into both open ocean and backwater in search of these apex predators. The captain will supply all the top-quality fishing gear, bait, and necessary licenses, so all you need to bring are your snacks and drinks. Along the way, you may also encounter mighty Goliath Grouper, and the powerful Bull and Blacktip Sharks will make for a memorable experience. Book now for a unique night fishing adventure that you won't forget! *Deposits are non-refundable.

Fishing

Starting At $450

Fishing Charters Naples FL | 4 Hour Charter Trip

Fishing Area: Naples

Fishing: Flats

Fishing Boat:

Playin Hooky • 20' Lowe • Max 3 guests (base trip price includes 3 guests)

Description:

Join Playin Hooky for a memorable 4-hour fishing trip through the scenic backwaters and flats of the iconic 10,000 Islands. Our experienced crew will guide you through these serene waters where you can catch a variety of species, including Black Drum, Sea Trout, Sheepshead, Snook, and even Tarpon. As you navigate this unique and peaceful location, you'll have the chance to reel in multiple fish, adding excitement to your day. If the weather allows, there may also be an opportunity to fish nearshore wrecks for an additional experience. Our 20' Lowe vessel accommodates up to 6 guests, and the base trip price covers 2 guests. *Deposits are non-refundable.

Charter Boats Naples FL | 8 Hour Charter Trip

Fishing

Starting At $850

Charter Boats Naples FL | 8 Hour Charter Trip

Fishing Area: Naples

Fishing: Inshore

Fishing Boat:

Playin Hooky • 20' Lowe • Max 3 guests (base trip price includes 3 guests)

Description:

Start your day at 8:00 AM and explore the unique backwaters of the 10,000 Islands, a truly special fishing destination. This full-day package offers ample opportunity to catch a variety of fish, including some perfect options for dinner. If conditions allow, you may also have the chance to fish nearshore wrecks for even more excitement. Target species include Goliath Grouper, Jack Crevalle, Black Drum, Snook, Tarpon, Mangrove Snapper, Redfish, Ladyfish, Spanish Mackerel, Spotted Seatrout, Flounder, Sheepshead, and more. With a full 8 hours on the water, this is a fantastic way to experience the rich fishing opportunities of the area. Deposits are non-refundable.

Fishing

Starting At $850

Naples Charter Fishing | 8 Hour Charter Trip

Fishing Area: Naples

Fishing: Wrecks

Fishing Boat:

Playin Hooky • 20' Lowe • Max 3 guests (base trip price includes 3 guests)

Description:

Join us for an exciting 8-hour nearshore wreck fishing trip in Naples, Florida. We’ll start by gathering fresh bait from our traps as we head out to an offshore wreck located just 3 miles from the shore, keeping land within sight. This productive location offers a variety of fish species, giving you the chance to use different techniques for catching your dinner. Target species include Black Drum, Cobia, Permit, Snook, Tarpon, Redfish, Spotted Seatrout, Tripletail, Sheepshead, and Speckled Trout. With 8 hours of fishing, you’ll have plenty of time to enjoy all that this fantastic fishing spot has to offer. *Deposits are non-refundable.

Hunting

Starting At $1,500

Hunting in Florida | Private 5 Hour Hunting Trip

Hunting Area: Naples

Hunting: Active hunting

Capacity:

Max 4 guests (base trip price includes 4 guests)

Description:

Join professional Python hunter Amy Siewe, also known as The Python Huntress, for an unforgettable guided hunt in South Florida. Amy will take you to her summer hot spots, where you’ll hunt the invasive Burmese pythons from the Snake Deck at the back of her truck. As part of this unique experience, Amy will also share her expert tips, strategies, and tricks of the trade, helping you sharpen your own hunting skills. This guided hunt provides not only the opportunity to track these large and elusive snakes, but also to learn from one of the best in the business. Don’t miss your chance to join this one-of-a-kind hunting adventure! *Deposits are non-refundable.

Vehicle

Playin Hooky

Boat Type:

Boat Guest Capacity:

Boat Length:

20 ft

Manufacturer Name:

Lowe

Model Year:

2018

Engine Manufacturer Name:

Mercury

# of Engines:

Horsepower Per Engine:

115

Maximum Cruising Speed:

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

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

Boat Type:

Boat Guest Capacity:

Boat Length:

20 ft

Vehicle Details

FAQs about Playin Hooky Fishing Charter

What are the trip rates for Playin Hooky Fishing Charter?

What's included in the trip price with Playin Hooky Fishing Charter?

What types of Fishing does Playin Hooky Fishing Charter offer?

What Fishing techniques does Playin Hooky Fishing Charter offer?

Which Fishing species can I catch with Playin Hooky Fishing Charter?

What is the cancellation policy for Playin Hooky Fishing Charter?

Reports and Expert Articles

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

April 8, 2025

Sing ray bow fishing! Imitation scallops for dinner!

Naples Fishing Trip

January 18, 2024

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.

Fishing Charters Naples FL - Ten Thousand Islands Backcountry Fishing

July 10, 2023

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

out of 5

Based on 7 ratings

recommended

Based on 7 recommendations

July 1, 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.

July 1, 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!

July 1, 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!

July 1, 2025

Went out with Playin' Hooky Fishing Charter in September '22 and it was epic! Landed some big redfish and even hooked into a monster tarpon. Best fishing trip ever!

July 1, 2025

Booked a trip with Playin' Hooky for July weekend last year and it was fantastic! The captain was friendly and patient, and we caught some beautiful snook. Highly recommend them!

July 1, 2025

Went out with PHFC in October and had a blast! Caught some nice-sized trout and even saw dolphins swimming by. Can't wait to go back out with them next year!