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Best Reviews

Naples Backwater Bite and Wreck Fishing

Work the 10,000 Islands Flats, Then Explore Nearshore Structure When Conditions Allow

Very Good

(1 Review)

5

Naples Backwater Bite and Wreck Fishing
Naples Backwater Bite and Wreck FishingMost Booked This Week
Naples Backwater Bite and Wreck Fishing

Naples

Naples Backwater Bite and Wreck Fishing

Fishing - Flats

Naples Backwater Bite and Wreck Fishing

Playin Hooky • 20' Lowe

Explore the winding backwaters and productive flats of Naples’ 10,000 Islands, with the possibility of fishing nearshore wrecks when weather conditions allow. This trip offers more variety than an outing spent in just one setting, giving guests opportunities to pursue Snook, Sea Trout, Sheepshead, Black Drum, Tarpon, and other local species. Beginners receive patient, hands-on guidance, while experienced anglers can enjoy moving between different waters and fishing situations. Bait, tackle, and equipment are provided, allowing guests to focus on casting, learning, and enjoying the surroundings. The 20-foot Lowe vessel is well suited for navigating shallow areas where larger boats may have difficulty reaching. From working quiet flats to fishing around structure, guests can experience several sides of the Naples fishery in one well-rounded trip.

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    Naples Face-to-Face Shark Fishing

    Feel the Power of Bull and Blacktip Sharks with Hands-On Guidance from Captain Dave

    Very Good

    (1 Review)

    5

    Naples Face-to-Face Shark Fishing
    Naples Face-to-Face Shark Fishing

    Naples

    Naples Face-to-Face Shark Fishing

    Fishing - Inshore

    Naples Face-to-Face Shark Fishing

    Playin Hooky • 20' Lowe

    Discover a different side of Naples fishing by pursuing Bull and Blacktip Sharks in productive coastal waters. Built for both first-time shark anglers and experienced guests, this trip focuses on the raw power and unpredictable runs that make these predators so memorable to catch. Captain Dave and his crew provide hands-on instruction throughout the outing, covering the techniques and safety practices needed to handle shark fishing responsibly. All required fishing gear, bait, and licenses are included, so guests can arrive ready for the experience. The well-equipped vessel provides a comfortable base while the crew searches for active areas and helps each angler stay prepared when a shark takes the bait. Bring your preferred snacks and drinks for an engaging Naples outing centered on powerful fish and practical guidance.

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      Naples After-Dark Shark Showdown

      Battle Bull and Blacktip Sharks Across Gulf Waters and Shadowy Backwaters with Captain Dave

      Naples After-Dark Shark Showdown
      Naples After-Dark Shark Showdown

      Naples

      Naples After-Dark Shark Showdown

      Fishing - Inshore

      Naples After-Dark Shark Showdown

      Playin Hooky • 20' Lowe

      Watch the Gulf sunset give way to a completely different fishing atmosphere as Captain Dave leads the search for Bull and Blacktip Sharks around Naples. Guests may move between open water and quieter backwater areas, adding variety to the experience and creating the possibility of encountering Goliath Grouper and other notable species along the way. The crew provides practical instruction on shark-fishing techniques and safe handling, making the outing approachable for first-timers while keeping seasoned anglers involved. Quality gear, bait, and required licenses are provided, allowing everyone to concentrate on the fishing. The well-equipped vessel offers a secure and comfortable platform as darkness settles over the water. Guests should bring snacks and drinks for a memorable evening shaped by powerful fish, changing scenery, and hands-on learning.

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        Take Aim After Dark in Naples

        A Two-Part Hunt That Turns Stingray Bowfishing into the Setup for Serious Shark Action

        Take Aim After Dark in Naples
        Take Aim After Dark in Naples

        Naples

        Take Aim After Dark in Naples

        Fishing - Inshore

        Take Aim After Dark in Naples

        Playin Hooky • 20' Lowe

        This is not a standard cast-and-wait fishing trip. The experience begins with guests using specialized bows to target Stingrays in Naples’ coastal waters. Successful shots can supply bait for the next challenge: fishing for hard-fighting Bull and Blacktip Sharks. Barndoor Skate may add another target as the trip unfolds, keeping the night varied and unpredictable. Captain Dave guides guests through each stage, from aiming and shooting to preparing for the strength of a shark on the line. Fishing equipment, bait, and licenses are included, and safety instruction is provided throughout the outing. Any unused Stingrays may be taken home and prepared as a scallop-like dish. For anglers looking to try something beyond traditional rod-and-reel fishing, this trip delivers an unusual combination of precision, teamwork, and powerful fish.

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          Naples Fresh-Bait Wreck Fishing for Cobia, Permit and Tarpon

          Gather Fresh Bait, Keep the Coast in View, and Work a Productive Wreck with Captain Dave

          Naples Fresh-Bait Wreck Fishing for Cobia, Permit and Tarpon
          Naples Fresh-Bait Wreck Fishing for Cobia, Permit and Tarpon

          Naples

          Naples Fresh-Bait Wreck Fishing for Cobia, Permit and Tarpon

          Fishing - Wrecks

          Naples Fresh-Bait Wreck Fishing for Cobia, Permit and Tarpon

          Playin Hooky • 20' Lowe

          The fishing begins before the boat reaches its main destination. Guests first collect fresh bait from the charter’s traps, adding a hands-on step that connects directly to the day’s fishing. From there, Captain Dave heads to a productive wreck only three miles off Naples, where land remains visible while anglers pursue anything from Cobia and Permit to Tarpon, Snook, Tripletail, and Sheepshead. The extended time on the water allows the crew to settle into the bite, adjust techniques, and explore the structure without rushing the experience. All necessary gear, bait, and fishing licenses are provided, with guidance available for every skill level. It is a well-rounded choice for guests who want wreck fishing and varied species without traveling far into the Gulf.

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            Naples 10,000 Islands Backwaters and Nearshore Wreck Bite

            Follow the Fish from Hidden Island Channels to Open Gulf Structure with Captain Dave

            Naples 10,000 Islands Backwaters and Nearshore Wreck Bite
            Naples 10,000 Islands Backwaters and Nearshore Wreck Bite

            Naples

            Naples 10,000 Islands Backwaters and Nearshore Wreck Bite

            Fishing - Inshore

            Naples 10,000 Islands Backwaters and Nearshore Wreck Bite

            Playin Hooky • 20' Lowe

            Cover more of Naples’ diverse fishing grounds as Captain Dave guides guests through the winding backwaters of the 10,000 Islands. These protected channels create opportunities to pursue Snook, Redfish, Mangrove Snapper, Spotted Seatrout, Sheepshead, and other local favorites in changing surroundings. When conditions cooperate, the boat can leave the islands behind and work nearby wrecks for a completely different style of action, with Spanish Mackerel, Goliath Grouper, and other species potentially entering the picture. This flexibility gives anglers more variety and allows the crew to respond to the day’s conditions. All fishing gear, bait, and required licenses are included, while hands-on guidance makes the experience accessible to beginners and enjoyable for seasoned guests. It is a complete look at both the sheltered and open-water sides of Naples fishing.

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              Eyes on the Road: South Florida Python Hunt

              Ride the Snake Deck with Amy Siewe and Learn How to Spot a Giant Hiding in Plain Sight

              Eyes on the Road: South Florida Python Hunt
              Eyes on the Road: South Florida Python Hunt

              Naples

              Eyes on the Road: South Florida Python Hunt

              Hunting - Active hunting

              Finding a Burmese python is a test of patience, sharp vision, and knowing exactly where to look. Amy Siewe takes guests into active summer territory aboard her truck, where the elevated Snake Deck provides a clear view of the surrounding habitat. Along the way, she explains the subtle shapes, shadows, and movements that can reveal a well-camouflaged snake. Once one is spotted, the experience shifts from observation to a carefully managed capture, with Amy directing every move and teaching safe handling methods. No previous hunting experience is required, and all necessary equipment is supplied. Because the outing is private, guests can ask questions and take an active role at a comfortable pace. It is a rare chance to join real invasive-python removal work with one of South Florida’s best-known hunters.

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              Playin Hooky Fishing Charter Fishing Trip Information

              TRIPS ARE SCHEDULED FROM 3RD WEEK OF SEPTEMBER

              Schedule a Trip Now!

              Good To Know’s

              • Trip is Child Friendly
              • Catch and Release Allowed
              • Quality Rods, Reels, & Tackle Are Provided

              Common Questions:


              What types of fishing trips does Playin Hooky Fishing Charter offer?

              • 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.


              How long are the fishing trips with Captain Dave?

              • 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.


              What are the rates for a fishing charter with Playin Hooky?

              • 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.


              Do I need a fishing license to fish in Naples with Playin Hooky?

              • 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.


              What is included in the price of the charter?

              • 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.


              Can I keep the fish I catch during the trip?

              • 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.


              What type of fish can we expect to catch?

              • 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.


              Is Playin Hooky Fishing Charter kid-friendly?

              • 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.


              How far in advance should I book a trip?

              • 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.


              What should I bring for the fishing trip?

              • 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!

              Playin Hooky Fishing Charter

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              Catch Memories in Naples!

              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!

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