Backcountry Fishing Charters

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

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

Brian Reams

Experience Backcountry Fishing Like Never Before

Enjoy a peaceful Islamorada backcountry fishing charter led by our expert Captain Drew where you can appreciate the solitude, natural beauty, and unique challenges of remote waters.

Drew is a second-generation fishermen who inherited his love of fishing from his dad. As a born-and-raised island local, he takes great pride in carrying on his father’s legacy and sharing the beauty of Islamorada with visitors.

Islamorada backcountry fishing charters

What You’ll Catch

Man and Woman in water with Shark caught
Man holding Snook
Man and woman holding Goliath Grouper
Goliath Snapper
Man and woman holding a Barracuda
Man holding Mutton Snapper
Mutton Snapper

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

Shallow Reef & Wreck Fishing

Explore some of the most beautiful coral reefs and artificial wrecks on a monumental reef and wreck fishing trip.

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An excellent trip for those looking to bring home fish for dinner.

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Easy fishing for first time anglers to have a successful day.

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A visual experience of beautiful coral, turtles, rays along the way.

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 family-friendly boats are perfect for bringing along your children or fur babies. Captain Drew loves taking little ones on their first fishing excursions!

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Local & Family-Owned

Our team is passionate about all things fishing and Islamorada! As proud long-time locals, we know everything there is to know about the area and what it has to offer.

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Passionate & Knowledgeable Captain

Captain Drew is a passionate and experienced captain born and raised in Islamorada. His father was a seasoned backcountry guide who taught him a great love and talent for fishing.

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Tailored Fishing Trips

We want every guest to have the best possible experience. That’s why we provide tailored trips for all ages to make your fishing dreams come true, regardless of experience level.

Flats, Inshore & Backcountry Fishing in Islamorada, FL

There are many species of fish local to Islamorada and they’re always biting! Guests can catch yellowtail snapper, goliath grouper, red grouper, black grouper, snook, spotted seatrout, mutton snapper, crevalle jack, black drum, tripletail, king mackerel, or cobia.

Backcountry fishing takes place in remote and often untouched bodies of water. This adventurous pastime combines hiking or backpacking with fishing, providing opportunities to catch species that are less impacted by human activity.

Enjoy a Day of Fishing in the Islamorada Backcountry

See what Monroe County has to offer! We are located near many local hotels, resorts, and attractions including Cheeca Lodge & Spa, Green Turtle Inn, Kon-Tiki Resort, Islamorada 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.

Book an Islamorada Backcountry Fishing Tour

Call or submit a form request to book a backcountry fishing tour for a select few or a large group. Everyone is welcome aboard our boat including experts and beginners! Captain Drew has spent his entire life fishing and enjoys guiding guests to isolated locations for a better backcountry fishing experience.

We also have additional package options including Islamorada family fishing charters, Islamorada deep sea 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.