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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Two Conchs Charters 
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Greater Amberjack caught while fishing in Naples FL

Switching Gears with Two Conchs Charters

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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

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

Things To Do 

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>

Naples Bay - Collier, FL Fishing Report on 10th Mar, 2026

AUTHOR

Dave Roberts

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Switching Gears with Two Conchs Charters

Naples Bay - Collier, FL

Playin Hooky Fishing Charter Available Trips

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