Deep Sea Fishing Charters

  • Child & Pet-Friendly Fishing Trips
  • Custom Trips & Packages
  • Experienced Second-Gen Captain
  • Local Family-Owned Business

Drew knows where the fish are and how to find them any time of the day — best guide in the Keys.

Brian Reams

Deep-Sea Fishing Charters in the Heart of the Florida Keys

Book one of our Islamorada deep sea fishing charters for an unforgettable adventure in the sport fishing capital of the world!

Explore our beautiful shorelines and catch big game with guidance from second-generation fishing guide Captain Drew.

Fishing in the Florida Keys - Fishy Business

What You’ll Catch

Giant Tarpon
Giant Tarpon

When to Catch Them

What you'll catch chart What you'll catch chart

What We Provide

  • Rods, reels, tackle & bait
  • Ice to store your catches
  • Water
  • Fishing licenses
  • Safety equipment
  • Fish cleaning, fileting & bagging
Captain Drew helping hold a fish with woman

What to Bring

  • Lunch & drinks
  • Sunscreen
  • Comfortable clothes
  • Hats & polarized sunglasses
  • Rain jackets
  • A good attitude & camera
  • No bananas on board!
Two male teenagers posing on the water with fish

Welcome Aboard!

Whether you’re a seasoned pro or a first-time fisherman, all experience levels are welcome on board. Captain Drew is here to guide you on your fun-filled fishing expedition.

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A Unique Islamorada Fishing Experience

Whether you’re going solo or bringing the whole family, get ready for an amazing adventure.

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Kid & Pet-Friendly Boats

Our state-of-the-art fishing boats are perfect for the whole family! Welcome aboard our stealthy 22′ Pathfinder tournament edition powered by a 200 Yamaha 4-stroke engine, Garmin electronics, and a 10 ft. Power pole blade with a Minn Kota trolling motor.

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Local Family-Owned Business

We are a family-owned company with a passion for deep-sea fishing and creating amazing memories. Captain Drew’s father was an experienced guide who helped develop his talent and enthusiasm for fishing.

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Passionate & Experienced Captain

Captain Drew is a lifelong fisherman and a native of Islamorada. He is a dedicated second-generation Captain who has fished around the county and is proud to call Islamorada his home.

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Tailored Fishing Trips

We specialize in deep-sea fishing trips for guests of all ages! Choose from our selection of fishing trip packages depending on what kind of experience you’re looking for.

Offshore & Deep Sea Fishing in Islamorada

Book an Islamorada deep sea fishing charter to take your vacation up a notch! With crystal-clear waters filled with different species of marine life, Islamorada is known as the Sport Fishing Capital of the World.

Fishy Business provides the necessary safety equipment, storage, and licenses for everyone on board. Our boat also has plenty of ice and storage space for beverages, snacks, personal items, and all your catches!

Book an Islamorada Deep-Sea Fishing Charter

Enjoy a day on the water in beautiful Monroe County with our Islamorada family fishing charters! We are conveniently located near several hotels and attractions including Cheeca Lodge & Spa, Green Turtle Inn, Kon-Tiki Resort, Moose Lodge, Caribbean Resort, Islander Resort, The Moorings, Theater of the Sea, History of Diving Museum, Florida Keys Brewing Company, Islamorada Brewing Company, and Islamorada Art Gallery.

Child & Pet-Friendly Deep Sea Fishing Trips

Book a deep-sea fishing charter for just a few guests or bring the whole family! Everyone is welcome aboard our boat including kids and dogs. Captain Drew has spent his entire life fishing and enjoys taking guests to coveted and isolated spots for an authentic experience.

Offshore fishing is a great opportunity for advanced anglers looking to land the catch of a lifetime or beginners who are eager to learn. We have several different fishing trip options including Islamorada backcountry fishing charters and Islamorada tarpon and shark fishing charters.

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See What Guests Are Saying About Us

Michelle Castellanos
Michelle Castellanos

I went fishing for the first time ever with Captain Drew, and had the time of my life! I caught more fish than I could’ve ever imagined and he exceeding all my expectations! He was very motivational and kept me in high spirits throughout the whole experience. I highly recommend Captain Drew to anyone looking for a great charter in the Florida Keys.

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Denise Friou
Denise Friou

I’ve gone out twice with Fishy Business Islamorada, and both times, we landed the fish we intended to catch. We did the bait fishing, then headed out for trout, mangrove snapper, and tarpon. Drew has great patience and is a good instructor for those wanting to learn and improve their fishing. The boat setup was great for small groups.

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Charles Castagna
Charles Castagna

Captain Drew made my Keys weekend the trip a lifetime. It seemed as though every time we cast a line, we had a bite within 30 seconds and a fish in the boat within a minute. This can be attributed to Captain Drew’s unparalleled knowledge of the best fishing spots Islamorada has to offer.

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Frequently Asked Questions

All private and group charters will have their deposits returned if cancelled 7 days prior to their charter reservation date. Any cancellations within 7 days of the trip will be charged a $250 cancellation fee. Any cancellation within 24 hours of the trip will be charged full price.

Unfortunately, I do not have a bathroom on board but typically we will be fishing within 15 minutes of a bathroom wherever we are so just ask the captain if you need to go!

Some parts of the year (April-September) we run into mosquitos and horse flies when fishing near Islands. Although it’s not common to get swarmed by bugs, I always suggest that people wear pants instead of shorts in case we come across them. I also keep a can of bug spray in the boat at all times if we need it.

During times of inclement weather we may be forced to reschedule or cancel charter trips. If this occurs, we will contact you personally to make further arrangements.