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Things To Do 

Things To Do In Naples

Changed it up today!
Two Conchs Charters 
@captjccarlson

Greater Amberjack caught while fishing in Naples FL

Switching Gears with Two Conchs Charters

Sing ray bow fishing! Imitation scallops for dinner!


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

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.

Single black drum fish caught in Naples, Florida

Naples Fishing Trip 

Spanish Mackerel

Fishing Charters Naples FL - Ten Thousand Islands Backcountry Fishing

Redfish

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!

Read expert Fishing articles, travel insights, and local stories from Playin Hooky Fishing Charter in Naples. Stay informed and inspired for your next adventure.

Naples Fishing Articles & Insights | 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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Mutton snapper being caught while fishing in FL

Two Spanish Mackerel and Spotted Weakfish, 17-inch fish caught while fishing and hunting in Naples

Sing ray bow fishing! Imitation scallops for dinner!

Unforgettable Fishing Journey with Naples, FL's Finest Charters

Get ready to reel in unforgettable memories with Playin' Hooky Fishing Charter in Naples, FL—book your adventure today and experience the thrill of landing trophy fish with our expert guides! Don’t wait—join us on the water and turn your next fishing trip into a story you’ll be telling for years!

Playin Hooky Fishing Charter, led by Captain Dave Roberts, offers customized fishing trips in Naples, Florida, designed for anglers of all experience levels. Whether you prefer inshore fishing or want to explore the unique waters of the 10,000 Islands, Captain Dave’s local knowledge ensures a productive and enjoyable fishing experience. Specializing in backcountry fishing, you’ll have the opportunity to reel in a variety of species, including redfish, snook, and tarpon, while discovering the natural beauty of Naples. For those looking for a more adventurous outing, shark fishing charters are also available, providing an exciting challenge on the water. With Playin Hooky Fishing Charter, you’ll enjoy a personalized fishing experience tailored to your skill level and interests. Captain Dave’s expertise in navigating Naples' abundant fishing grounds guarantees a memorable day on the water, whether you're a seasoned angler or new to the sport. Our charters target a range of species such as Goliath Grouper, Jack Crevalle, Mangrove Snapper, Spanish Mackerel, and more. We depart from the Port of the Islands Marina (525 Newport Dr, Naples, FL 34114) to offer a top-tier fishing experience in the Gulf of Mexico. Come join us for a day of great fishing and create unforgettable memories.

Captain Dave Roberts is the guiding force behind Playin' Hooky Fishing Charter, bringing decades of experience and a lifelong passion for fishing to every trip. A native of Naples, FL, Captain Dave has spent his life navigating the waters of Southwest Florida, developing an intimate knowledge of local fishing spots, seasonal patterns, and the behavior of key species like tarpon, snook, and redfish. His expertise, combined with a personable and approachable demeanor, has earned him a reputation as one of the region’s most trusted fishing guides. Guests consistently appreciate his ability to personalize trips, making them enjoyable for both experienced anglers and newcomers. Captain Dave’s approach to guiding goes beyond catching fish. He takes pride in teaching and mentoring anglers of all skill levels, sharing techniques, tips, and insights that enhance each outing. From introducing beginners to the basics of casting and baiting to offering seasoned anglers advanced strategies, Captain Dave ensures that everyone gains knowledge and confidence on the water. His adaptive style allows each trip to align with individual goals, whether pursuing trophy tarpon, exploring shallow backwaters for snook, or seeking exciting inshore species like redfish. Building lasting relationships with his clients is central to Captain Dave’s mission. Many guests return year after year, drawn by his dedication, professionalism, and deep appreciation for the natural beauty of Southwest Florida’s waterways. His enthusiasm for both fishing and the environment creates a rewarding, memorable experience for every guest. Through his guidance, anglers not only leave with impressive catches but also with a greater understanding of the local waters and the thrill of learning from a true expert. About The BoatThe Playin’ Hooky fishing boat complements Captain Dave’s expertise, providing a safe, reliable, and fully equipped platform for every trip. Designed for inshore and backcountry excursions, the boat allows access to the hidden gems of the 10,000 Islands and shallow coastal waters. It is stocked with top-quality fishing gear, bait, and tackle, while advanced navigation and safety features ensure peace of mind. Regular maintenance and careful attention to detail by Captain Dave guarantee that every outing runs smoothly, letting guests focus entirely on the fishing and the experience of exploring Naples’ spectacular waters.

Meet Your Captain Dave Roberts from Playin' Hooky Fishing Charter

Book a 4-hour inshore shark fishing trip in Naples, FL. Expert guides, gear provided. Perfect for all skill levels.

Inshore Sharks

Naples Shark Fishing: 4-Hour Inshore Adventure

Join our 4-hour inshore night shark bowfishing trip in Naples, FL. Perfect for all skill levels. Book now!

Bowfish Blast

World-Class Bowfishing Charter in Naples

Join The Python Huntress for a 5-hour active hunting adventure in South Florida. Learn to track and capture invasive pythons safely. Book now!

Python Hunt

Expert-Guided Python Hunt in South Florida

Book a premium 4-hour inshore night shark fishing trip in Naples, FL. Expert guides, all gear provided. Reserve now!

Night Sharks

Naples Night Shark Fishing: 4-Hour Adventure

Book a top-rated 8-hour wreck fishing trip in Naples, FL. Target cobia, tarpon & more with Playin' Hooky Charters!

Wreck Fishing

Naples 8-Hour Wreck Fishing Adventure

Experience world-class flats fishing in Naples, FL. Target trout, sheepshead & more on this 4-hour guided trip. Book now!

Hooky Flats

Top-Rated 4-Hour Flats Fishing in Naples, FL

Book a top-rated full-day inshore fishing trip in Naples, FL. Target diverse species with expert guides. Reserve now!

Full Day Fun

Naples FL's Premier 8-Hour Inshore Charter Trip

Family Friendly Florida Fishing Charters

Inshore and Nearshore Fishing In Naples

Top Of The Line Fishing Gear Provided

Fishing License is Covered!

Common Questions: What types of fishing trips does Playin Hooky Fishing Charter offer?<ul><li>Playin Hooky offers a variety of trips, including inshore fishing, backcountry fishing, shark fishing, and trips to the 10,000 Islands. Each trip is designed to suit anglers of all skill levels and interests.</li></ul> How long are the fishing trips with Captain Dave?<ul><li>Trips typically range from half-day (4 hours) to full-day (8 hours) adventures, depending on your preference. Custom trip lengths can also be arranged upon request.</li></ul> What are the rates for a fishing charter with Playin Hooky?<ul><li>Rates vary depending on the type and length of the trip. Generally, half-day trips start around $400, while full-day trips can range from $700 to $900. Prices may vary based on the season and specific requirements.</li></ul> Do I need a fishing license to fish in Naples with Playin Hooky?<ul><li>No, Captain Dave takes care of all licensing needs. All passengers are covered under the charter’s fishing license, so you don’t need to worry about getting your own.</li></ul> What is included in the price of the charter?<ul><li>All charters include fishing gear, tackle, bait, licenses, and the expertise of Captain Dave. Water and ice are also provided, but feel free to bring your own snacks and drinks.</li></ul> Can I keep the fish I catch during the trip?<ul><li>Yes, you can keep fish that are within Florida’s regulations. Captain Dave will clean and fillet your catch so you can take it home, or you can choose to practice catch and release.</li></ul> What type of fish can we expect to catch?<ul><li>Depending on the season and trip, you can catch snook, redfish, tarpon, trout, and even sharks. Each trip offers a chance to target different species based on conditions and your preferences.</li></ul> Is Playin Hooky Fishing Charter kid-friendly?<ul><li>Yes, Captain Dave welcomes anglers of all ages, making it a great option for a family fishing adventure. He’s experienced in teaching kids how to fish and ensures a safe, fun experience for the whole family.</li></ul> How far in advance should I book a trip?<ul><li>It’s recommended to book at least a few weeks in advance, especially during peak fishing seasons, to ensure availability. However, last-minute bookings may be possible depending on the schedule.</li></ul> What should I bring for the fishing trip?<ul><li>Bring sunscreen, sunglasses, a hat, and any personal snacks or drinks you’d like. A cooler is provided on the boat, so you can keep your refreshments cold. Don't forget your camera to capture the memories!</li></ul>

Air Fee

Bait Fee

Divemaster Fee

Mate's Fee

Nitrox Fee

Service Fee

State Taxes

Trimix Fee

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.

Black Drum

Sea Trout

Sheepshead

Snook

Tarpon

Playin Hooky

4 hrs 

Half Day Guided Fishing Trip In Naples, Florida  - Trout, Sheepshead And More

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.

Blacktip Shark

Bull Shark

Half Day Guided Morning Shark Fishing Trip In Naples, Florida

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.

4.00hour

Half Day Guided Night Shark Fishing Trip In Naples, Florida

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.

Half Day Guided Night Shark Bowfishing Trip In Naples, Florida

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.

Crevalle Jack

8 hrs 

Full Day Guided Fishing Trip In Naples, Florida - Sheepshead, Mackerel And More

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.

Cobia

Permit

Full Day Guided Fishing Trip In Naples, Florida - Cobia, Tarpon And More

Bait's fee

Mate's fee

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.

5.00hour

Half Day Guided  Python Hunting Trip in South Florida

Great Guide

Great For Top Anglers

Best Spots

Good with Kids

Captain

Freshly caught salmon being held on fishing boat deck over ocean waters

Two people standing on dock next to charter fishing boat with Lake Michigan salmon and trout fishing signage

Angler holding large Chinook salmon on fishing boat in open ocean waters

Chinook salmon caught on fishing boat during sunset on open water

Fishing charter success with salmon catch on boat deck with fishing rods and ocean backdrop