Your Captain
Dave Roberts
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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.
What's Included
This guide offers trips that you are able to take home your catch.
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Your Guide has some important details about your trip with them.
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Read about the licensing details that is / is not covered in the below trips.
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This guide offers trips with nature and wildlife views.
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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
This guide offers trips that you are able to take home your catch.
Show More
Your Guide has some important details about your trip with them.
Show More
Read about the licensing details that is / is not covered in the below trips.
Show More
This guide offers trips with nature and wildlife views.
Show More
When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
Show More
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.
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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.
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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.
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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.
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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.
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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.
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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.
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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
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.
Playin Hooky
Boat Type:
Boat Guest Capacity:
3
Boat Length:
20 ft
Vehicle Details
Sing ray bow fishing! Imitation scallops 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.
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
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!