Miss Penny Islamorada Fishing Charters
Are you considering your next family vacation? Looking to compete in a tournament? Perhaps you’re planning a team-building experience for your office? Or maybe you’re looking to enjoy some quality time on the water with your significant other? If any of these sound like you, come down to the Florida Keys and discover some of the finest deep-sea fishing Key Largo and Islamorada have to offer.
Miss Penny is a clean, fast, air-conditioned, comfortable 43′ Tiara Yacht 4300 Express powered by twin, turbo charged Cummins QSM11 Diesels. We offer everything from Snapper to Swordfish for all ages and skill levels.
Miss Penny Split Charters
Looking to enjoy deep-sea fishing on a budget? Consider opting for a split charter. Up to a maximum of 4, the cost per angler is determined at the charter’s start time, calculated by dividing the total charter duration by the number of anglers.
Note: Fishing on a split charter is contingent on it being fully booked. If a private charter secures the same day and time before the split charter is filled, the private charter takes precedence, and a full refund will be issued to you.
400 ¾ Day Anglers
500 Full Day Anglers
6 Hrs
8 Hrs
Sold by Seat
*Prices subject to change without notice
Half Day Fishing Charter
Opt for our briefest adventure with a half-day trip, encompassing 4 hours of reef and wreck fishing tailored to your preferences. The excursion commences with the excitement of capturing live bait. Subsequently, we engage in a collaborative decision-making process: either daringly aim for a sizable catch on the wrecks or anchor up at the reef to pursue Snapper and Grouper. The choice is yours!
¾ Day Fishing Charter
Introducing our “Dinner and a Show” package: a thrilling 6-hour fishing expedition just a short distance from the coastline. Our journey kicks off at the reef, where we reel in live bait and some delectable Snapper and Grouper for a satisfying dinner. With our catch safely stored, we venture offshore to nearby wrecks, seeking larger game such as Sailfish, Wahoo, Tuna, Amberjack, and even Sharks for an action-packed experience!
Full Day Fishing Charter
Join us for an exhilarating full-day fishing excursion spanning 8 hours. Start your day with the excitement of catching live bait on the patch reefs. Depending on the bait secured, our adventure will take us in search of Sailfish, Wahoo, Tuna, or Mackerel near the wrecks initially. Later in the day, we’ll anchor up at the reef to target Snapper, Grouper, Amberjack, and other species. The sequence of activities is subject to change based on prevailing conditions and fishing success.
Swordfish Charters
The allure of swordfishing charters has grown, attracting anglers globally to pursue these coveted deep-sea predators. Our daytime swordfish expeditions plunge into depths ranging from 1400 to 1800 feet, promising both excitement and challenge. Experience the unparalleled thrill of capturing a swordfish while relishing the chance to encounter other captivating species on the way. Choose Miss Penny Charters for an unforgettable adventure at the heart of Islamorada, where we’ll guide you through an extraordinary experience.
Miss Penny – Your Premier Destination for Islamorada Fishing
No matter your age, your journey to the Florida Keys will remain etched in your memory for years to come. Are you ready for an unparalleled deep-sea fishing adventure? Miss Penny stands as the leading Fishing Charter in Islamorada, committed to delivering an exceptional experience with every customer, every time, surpassing all others.
Creating Unforgettable Memories
Relax and let Miss Penny handle all the details of your Islamorada fishing trip while you enjoy your vacation! Our top priority is ensuring that our guests have the most exceptional experience possible. Enjoy all the comforts of our air-conditioned, tournament-rigged, 43-foot Tiara, including a bathroom and a spacious cockpit.
Local Expertise
Our expertise in Florida fishing charters comes from our daily lives in the area – we are familiar with all the sites and hidden bays that we can recommend to you. While our primary fishing grounds are in Islamorada, we can also reach Key Largo fishing charters waters.
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Flexible Packages to Suit Your Needs
Choose from a variety of options for half-day, three-quarter, or full-day Florida fishing charters, tailored to your preferences and budget. Miss Penny stands out among Florida Keys fishing charters with its competitive pricing and exceptional service.
Catch a Variety of Fish
Whether you’re after Swordfish, Sailfish, Mahi-mahi, Snapper, or Grouper, Miss Penny has you covered. Our luxurious Florida Keys fishing charters can accommodate up to six passengers in style.
Commemorate your once-in-a-lifetime trip with our unique Miss Penny UV Performance shirt – the perfect souvenir!
Dependable, High-Quality Customer Service
Our fishing charter crew is dedicated to ensuring that your vacation runs as smoothly as possible. Our phone lines are open 24/7 to provide the highest level of customer service and address any questions or concerns.
The Story Behind Your Next Islamorada Fishing Charter
Ever wondered about the heart and soul behind your favorite fishing charter? Well, let me tell you a story about passion, family, and a boat named Miss Penny. It’s a tale that begins with a childhood dream and evolves into a legacy on the water.
From Trout Pond to the Florida Keys: A Lifelong Obsession
It all started with a simple trip to a trout pond. I was just three years old, and my mom took me fishing in California. That first tug on the line? I was hooked. Suddenly, it was, “Let’s go back! Let’s go back!” every single day.
Even when I couldn’t be on the water, I was soaking it all in. Watching fishing shows, devouring online content—I couldn’t get enough. It was an eye-opening experience that ignited a lifelong passion.
My mom always encouraged me to follow that passion. She knew being a fishing guide was my dream, and she wanted me to pursue it. But life, as it often does, threw a few curveballs.
I remember telling her I was going to join the army right before high school graduation. She wasn’t thrilled. “You need to go out and fish,” she said. “You need to go down to Florida, live there full-time, and be a fishing guide.” We had a huge argument. I was stubborn, and so was she. I joined the army anyway. But guess what? She was right. Look where I am now, doing exactly what she envisioned.
When I finally brought my mom down to the Florida Keys, she loved it. More than anything, she loved seeing me doing what I love. She was content to chill on the beach with a book, but she always made time to see me come back from the Islamorada fishing charter trips. She even came out on a few of them! Seeing me catch those fish? It was pretty cool for her. I remember her saying, “Man, the look you get on your face when you catch those fish is something else for sure.”
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Finding Strength: Lessons from Miss Penny
Life isn’t always smooth sailing. In 2008, my mom was diagnosed with white blood cell cancer. It was one of the hardest things our family has ever gone through. I was still pretty young, and I didn’t fully grasp how serious it was at the time.
But seeing her strength, her composure, as she went through treatment? It was inspiring. It showed me that anything is possible. If she could face that challenge with such grace, I could face anything.
The Birth of a Legacy: The Story of the Miss Penny
Fast forward to August 2023. We bought a boat. It needed some serious TLC. The previous owner had a few boats, and this one had been neglected. My captain, Chad, and my mate, Matt, worked tirelessly for almost 20 weeks straight, breathing new life into her. New upholstery, a complete overhaul—it doesn’t even look like the same boat anymore.
When I first bought it, I was racking my brain for a name. The Broad Bill? Something swordfish-related? Nothing felt right. Then, one night, it hit me. It took me long enough, honestly. There was only one name that truly fit: Miss Penny.
She’s the whole reason this charter exists. She’s the reason I even took on this adventure. There was no other name that could possibly capture the essence of what we’re doing.
Naming the boat after her is my way of honoring her legacy. It’s my gift to her. When people step on board, the first thing they see is “Miss Penny.” They ask about it. They want to know the story behind the name. And that’s exactly what I want. I want to share her story, her impact, with everyone who comes on this boat.
Sharing the Passion: The Islamorada Fishing Experience
Down here in the Florida Keys, there’s a real sense of community among anglers. We’re known as the sport fishing capital of the world, and people come from all over to experience it. Some have never even held a fishing rod before!
That’s what I love most. Taking people out on the water and seeing the transformation in just a few hours. Anyone can hire a captain and watch them work. But we want our clients to feel involved. We want them to feel like they’re part of the experience. Because they are. They’re sharing my passion, my favorite place in the world.
And seeing the look on someone’s face when they catch their first fish? There’s nothing like it. Maybe, just maybe, we’re igniting a lifelong passion in them, too.
When you step onto the Miss Penny, I want you to understand where it comes from. You’re stepping onto something that is a legacy. This is my way of honoring my mom and keeping her memory alive. I want as many people as possible to know who she was and what she did for us. Naming this boat after her, having people see that name and ask questions? It’s the perfect way to keep her spirit alive.
Meet Captain Chad: Your Guide to an Unforgettable Adventure
“Hi, my name is Chad Puit, and I’m the captain of the Miss Penny down in beautiful Islamorada, Florida. If you come fishing with us, it’s going to be a good time. It’s going to be fun, and it’ll be very informative. We have all the amenities you need to fish. We have a beautiful boat that’s 45 feet long, with air conditioning inside and out. We have toilets, top-of-the-line tackle, and very friendly service. Anything you need, we can make happen. If you want anything special, just let us know ahead of time, and we’ll make it happen. We like to create memories. We love to catch fish, but in the end, we’ll create memories. You get to come do something in a beautiful, wonderful place – the Florida Keys. You’re creating a memory that you can take with you for the rest of a lifetime. We hope to see you soon!”
Ready to Make a Memory?
So, are you ready to experience the magic of the Florida Keys and create memories that will last a lifetime? Come join us on the Miss Penny for an unforgettable Islamorada fishing charter adventure.
Address:
Robbie’s Marina
77522 Overseas Highway – Charter Dock Slip 8
Islamorada, FL 33036