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Choose Your Fun Adventure

We know choosing the right fishing or island-hopping charter can feel like a big decision. Will it live up to your expectations? Will the guide truly know the best spots? We get it—and that’s why we do things differently.

  • Experienced & trusted captain who knows these waters inside and out
  • Tailored trips—whether you want serious fishing, a family-friendly adventure, or a bit of both
  • No guesswork—just a seamless, stress-free experience from start to finish

From sunrise-to-sunset fishing to shelling, island exploring, and more—we’re here to make your trip unforgettable.

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Day Fishing

4 - 8 hrs

4 Hours Minimum
All Gear is Included
Top-notch Rods and Reels
Bait & Tackle
Fishing License

Night Fishing

4 hrs

4 Hours Minimum
All Gear is Included
Top-notch Rods and Reels
Bait & Tackle
Fishing License

Shelling

4 - 8 hrs

4 Hours Minimum
All Gear is Included
Shelling Gear
Life Jackets for All Ages

Island Adventure

6 - 8 hrs

8 Hours
All Gear is Included
Shelling Gear
Life Jackets for All Ages

Federal Offshore Fishing

8 - 10 hrs

All Gear is Included
Top-notch Rods and Reels
Bait & Tackle
Fishing License

Pulley Ridge Expeditions

15 - 18 hrs

2 licensed 100-Ton Master Captains
Limited-availability premium Gulf expeditions
Can be extended up to 25 hours
Premium extended experience

Fishing trips.
Night or day.

4 - 8 hrs

Day Fishing
BAY BOAT

4 hrs

Night Fishing
BAY BOAT

8 - 10 hrs

Offshore Fishing
CONTENDER 39ST

Experience world-class fishing in Southwest Florida, fully customized to your preferences. Whether you're after trophy Tarpon, Snook, Redfish, Sea Trout, Tripletail, Cobia, Snapper, Grouper, or more, we’ll craft the perfect trip for you.

  • Choose from half-day, full-day, or sunset-to-sunrise excursions
  • Try night fishing for monster sharks
  • Take a break at a water-access-only restaurant
  • Enjoy a completely personalized experience—we handle everything

Think of us as your concierge on the water—just tell us what you want, and we’ll make it happen.

All gear, bait, and fishing licenses included.

4 Hours Minimum
Day Fishing
Night Fishing

Top of the line Robalo and Contender boats powered by Yamaha engines

All Gear is Included
Top-notch Rods and Reels
Bait & Tackle
Fishing License

4 Hours Minimum

Top of the line Robalo and Contender boats powered by Yamaha engines

All Gear is Included
Shelling Gear
Life Jackets for All Ages

Shelling
Excursions

4 - 8 hrs

BAY BOAT

Price includes 2 people; shelling gear provided when needed.

Let us guide you to the most abundant shelling locations on Florida’s west coast. From rare finds to breathtaking treasures, you’ll collect stunning shells in pristine, boat-access-only areas.

  • Expert-guided shelling experience
  • Access to the best, untouched shelling spots
  • Shelling gear provided when needed

Island
Adventures

6 - 8 hrs

BAY BOAT

6 - 8 hrs

CONTENDER 39ST

Pricing for the trip is based on the boat selected.

Embark on a private, boat-access-only journey to the hidden gems of SW Florida. Explore untouched islands, fish in crystal-clear waters, and discover stunning marine life—including dolphins, manatees, and exotic birds.

  • Chase breathtaking sunsets
  • Hunt for giant conch shells
  • Relax on a secluded island—picnic, play, or sway in a hammock
  • Dine at exclusive waterfront restaurants

This excursion is fully customizable—you dream it, we make it happen!

8 Hours+

Top of the line Robalo and Contender boats powered by Yamaha engines

All Gear is Included
Shelling Gear
Life Jackets for All Ages

Pulley
Ridge

15 - 18 hrs

Extendable (up to 25 hours)

Two 2 licensed 100-Ton Master Captains are onboard every Pulley Ridge expedition, ensuring maximum safety, redundancy, and long-range capability.

These Limited-availability premium Gulf expeditions are designed as premium, extended-range experiences for serious anglers seeking something beyond the ordinary.

  • 2 licensed 100-Ton Master Captains
  • Limited-availability premium Gulf expeditions
  • Can be extended up to 25 hours
  • Premium extended experience

Meet Our Captains

captain-john

Captain John

Anglers Choice

Licensed

30+ Years Experience

With over 30 years of experience fishing the backcountry and nearshore waters of Southwest Florida, Captain John Gauntt knows these waters like the back of his hand. From the 10,000 Islands to Boca Grande, he’ll take you to the best fishing spots, ensuring you not only land impressive catches—but make lifelong memories, too.

Whether you're after a high-energy fishing trip, a family-friendly shelling adventure, or an exciting night excursion targeting Florida’s most impressive predators, your trip is completely customizable. Just tell him what you want, and he’ll make it happen.

Captain John is on the water up to six days a week- so he always knows exactly where the action is.

What's the best part of his job? Simple: Doing what he loves! A lifelong fisherman, Captain John thrives on being on the water, guiding guests of all ages and experience levels, and helping them reel in Southwest Florida’s world-famous species.

Captain Parker

Licensed

30+ Years Experience

Captain Parker Gauntt grew up casting lines and chasing big fish in the waters of Southwest Florida alongside his brother, Captain John. Over the years, he’s mastered the art of targeting some of North America’s most sought-after species, ensuring every trip puts you right where the bite is hottest—whether inshore or nearshore.

With Day 5, Captain Parker is all about customizing your adventure. Want a relaxing island getaway? A thrilling day of battling hard-hitting sport fish? Or maybe an adrenaline-pumping night chasing Florida’s apex ocean predators? Whatever your dream trip looks like, he’ll make it happen.

Captain Parker welcomes anglers of all experience levels, from first-timers to seasoned pros. His mission? To make sure you have the gear, guidance, and excitement needed to land that once-in-a-lifetime catch. And if there’s one sound he loves more than anything—it’s the scream of a drag peeling off line.

When he’s not leading unforgettable fishing excursions, you’ll find him on the water with his brothers or his own kids—raising the next generation of dedicated, die-hard anglers.

Ready for the fishing trip of a lifetime? Captain Parker’s got you covered!

captain-parker
captain-josh

Captain Josh

Anglers Choice

Licensed

10+ Years Experience

With over 10 years of experience navigating inshore and offshore waters, Captain Joshua Cribbett is a seasoned guide who knows how to put you on the fish. His deep passion for fishing and commitment to sharing his expertise ensure that every trip is not just about the catch—but also about the experience.

Whether you're chasing trophy fish or simply looking to relax and enjoy nature, Captain Josh provides personalized trips tailored to all skill levels. His friendly, professional approach makes every outing both educational and exciting.

As a strong advocate for sustainable fishing practices, he’s dedicated to creating unforgettable experiences while respecting and preserving the environment.

Last Call on Our Best Deal

Don’t miss this season’s biggest saving offer!

What Our Clients Say

“I recently had the pleasure of embarking on a fishing adventure with Day 5 Charters and it was truly an amazing experience. From the moment we set sail, I could tell that this was going to be a fun and memorable trip. The captain and crew were incredibly knowledgeable and made sure we had everything we needed for a successful day of fishing. But what really stood out to me was the beautiful island adventure we had while on the boat. The stunning shell collection on display was a sight to behold and added an extra layer of excitement to the trip. It was clear that the crew had put a lot of effort into creating a unique and enjoyable experience for their guests. Overall, I highly recommend Day 5 Charters for anyone looking for a fun and unforgettable fishing adventure. The combination of amazing fishing and island exploration made for a perfect day on the water. Thank you to the entire team for an incredible experience. I can't wait to come back and do it all again!”

Bill M.

“Had an amazing time working with Day 5 Charters! Everything from initial phone conversations to day of fishing went perfectly. John and Parker are great to work with, highly recommended!”

Dave A.

“Absolutely one of the most memorable experiences for our family of 6. My kids Are 10, 8, 6, and 3 and they had a blast. We did an all day island adventure and caught some fish to eat. Did some swimming and shelling and enjoyed fighting some sharks on the line too. Captain John was extremely friendly and kind. He helped my 6 and 3 year old daughters reel in some trout. I can’t wait to go out with Day 5 Charters again. They know their stuff and enjoy doing it. If you are looking for a charter in the Ft Myers area. Look no further.”

Matthew K.

FAQ

Fort Myers
Beach Location

Meeting Place: Joe’s Dockside Marina
Address: 18400 San Carlos Blvd., Fort Myers Beach, FL 33931
Phone: (239) 994-4027

* We can accommodate local/home dock pick ups (accommodation and additional fee contingent on distance from Joe’s Dockside Marina). Call to inquire.