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.

Full Day Fishing Charter

8 hours • Up to 6 people • $2000

¾ Day Fishing Charter

6 hours • Up to 6 people • $1600

Half Day Fishing Charter

4 hours • Up to 6 people • $1200

Swordfishing Charters

Up to 10 hours • Up to 6 people • $2500

Split/Shared Charters

6 or 8 hours • Up to 4 • Sold by the seat!!

Upcoming Split Charters

No Split Charters are currently running. Click here, or call (305)209-5594 to start one.

Drop us a line and we’ll hook you up!

    Contact us

    Robbie’s Marina
    77522 Overseas Highway – Charter Dock Slip 8
    Islamorada, FL 33036



    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.

    More Than Just Fishing

    For those looking to stay active on vacation, we offer various optional extras beyond fishing. Whether you’re interested in biking, kayaking, stand-up paddleboarding, or custom-made vacations and personalized services, we’re here to help you make the most of your Islamorada fishing charters experience.

    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.