Islamorada Fishing Guides & Private Charters

Private Offshore & Inshore Fishing Charters in Islamorada, Florida Keys

A Fishing Guru

Two Marinas, Three Boats, Endless Fishing

Islamorada is known for world-class fishing, and our charters are built to match it. Offshore trips run out of Three Waters Marina on our 39’ Contender Big Guru and our 26’ Pathfinder Pirate Guru, built for speed, comfort, and long runs into productive blue water. Inshore and backcountry charters leave from Angler House Marina aboard our 24’ Shallow Sport Little Guru, designed for quiet flats, mangrove shorelines, and calm, shallow water.

Contender boat logo.
Stylized black text logo reading 'Shallow Sport' with angular, sharp-edged typography and a decorative underline.
Pathfinder Boats logo in black and white
Meet The Captains
Smiling young man sitting on a boat holding a large silver fish with water and trees in the background.
Angler holding a large mahi-mahi (bull dolphin) with vivid green and yellow coloring on a charter boat in the open ocean under a blue sky
Our Charters

Two Ways to Fish the Florida Keys

From deep sea action offshore to calm-water days in the backcountry, our private charters give you two great ways to fish Islamorada.

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WHat's Biting
Three men on an Islamorada fishing charter shout and smile in excitement after catching a large sailfish.
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Departs from Three Waters Marina

Deep Sea Fishing & Offshore Fishing

Offshore trips focus on blue-water species such as mahi, tuna, sailfish, wahoo, snapper, and grouper depending on the season and the conditions. If you want a full day of action offshore with a captain who knows these waters, this is the trip.

Half Day & Full Day  
Offshore - Deep Sea
Starting at $1000
6 guests
A woman happily holds up a large silver game fish caught while inshore fishing
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Departs from Angler House Marina

Inshore & Backcountry Fishing

Inshore trips are designed for quiet flats, shallow channels, and close-range fishing. This is where the tarpon, snook, redfish, and trout spend their time. Conditions are calm, the scenery is classic Florida Bay, and the style of fishing is as hands-on as it gets.

Half Day & Full Day  
Inshore - Backcountry
Starting at $650
5 guests
Our Boats

Meet the fleet

Two modern boats, each built for a different style of fishing  and both rigged for a solid day on the water.

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Fishing boat with yellow and green design anchored in clear turquoise water under a blue sky with scattered clouds.

'Big Guru', 39’ Contender

Big Guru is our 39’ Contender ST, powered for long runs offshore and equipped with the range, speed, and stability that deep sea fishing demands. The layout is clean and open, giving anglers plenty of room to work lines when the bite turns on. Electronics include advanced Garmin chartplotting, sounder, and radar all dialed in to keep us on fish throughout the day.

Departs from Three Waters Marina
Offshore - Deep Sea
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6 guests
A mint green and white flats fishing boat floating on clear green water under a blue sky with scattered clouds.

'Little Guru', 24’ Shallow Sport

Little Guru is our 24’ Shallow Sport, designed specifically for the flats, mangroves, and shallow channels of Florida Bay. The draft is minimal, the ride is quiet, and the deck layout gives anglers a stable platform for sight casting. It’s an ideal setup for tarpon, snook, redfish, and trout.

Departs from Angler House Marina
Inshore - Backcountry
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5 guests
A Fishing Guru’s new 26’ Pathfinder inshore and offshore fishing charter. It rests in the still waters of Islamorada, Florida.

Pirate Guru, 26’ Pathfinder

Meet Pirate Guru, our brand-new 26' Pathfinder! The ultimate Islamorada hybrid, this high-performance vessel lets us target the shallow backcountry flats for Tarpon and Snook, or head offshore to chase Sailfish and Mahi. Featuring expansive casting decks, tournament-grade livewells, and a smooth-riding stepped hull, Pirate Guru is built to deliver the ultimate dual-threat fishing charter.

Departs from Three Waters Marina
Offshore - Deep Sea
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6 guests
Inshore - Back Country
Target Species

What we're catching in Islamorada

View the Fishing Calendar

Sailfish

When the air is cold, the bite is hot. Winter is best time to catch sailfish and will stick around through spring.

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Mahi Mahi

Peak season in summer when large schools are abundant, but can be caught other months in small quantities.

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Tuna

Can be targeted in abundance during the spring months, but are occasionally caught in winter and summer as well.

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Grouper & Snapper

Strong and Tasty. will test your strength getting it to your dinner table. Snapper caught year-round, grouper during season.

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Tarpon

A true Islamorada specialty. Peak spring through early summer.

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Redfish

Stalk the shallow waters of the everglades in pursuit of this tasty, tailing, hard fighter.

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Snook

Found in mangroves and creeks; responsive to both artificial and live baits.

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Spotted Seatrout

Lots of fun, rod bending action while targeting Seatrout on the grassbeds of the everglades.

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Charter Highlights

What to expect on your charter

Trips are private, structured around the conditions, and paced to match your experience level. The captains explain the plan before you leave the dock, handle the technical work on the water, and keep the day running smoothly so you can focus on the fishing.

All bait, tackle & fishing licenses included

Bottled water & ice provided

Clean, well-rigged boats and gear

Catch cleaned & bagged after the trip

Two of A Fishing Guru’s fishing charter boats parked near Three Waters Marina in Islamorada, Florida. The water is a beautiful bluish-green hue and the sky is clear.
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Private Group Fishing Charters

Aerial view of the Overseas Highway bridge stretching across turquoise Florida Keys waters between islands, with coral reef flats visible below

Fishing guru bachelor party charter

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Three women laughing and embracing on a boat at golden hour, with calm ocean water and a glowing coastline behind them

Fishing guru bachelorette party charter

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Four friends laughing together on a boat in bright sunlight on the open ocean, wearing sunglasses and summer clothing

Fishing guru birthday party charter

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Snook in the ocean chasing a lure while fishing in Islamorada, FL.

Fishing guru corporate events charter

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Silhouettes of a couple fishing together from the bow of a boat at sunset, with golden light reflecting on calm water and forested hills in the background

Fishing guru couples charter

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A young girl in a red-striped bandana holds a fishing rod over turquoise water on a boat, guided by her mother in a pink cap standing behind her

Fishing guru family charter

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Ready to Fish Islamorada?

Offshore or inshore, half day or full day, your charter is private, fully equipped, and run by captains who know these waters well. Pick the trip that fits your style and we’ll handle the rest.

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Angler holding up a blackfin tuna on the stern of a charter boat in the open ocean, with deep blue water and a clear blue sky behind him
FAQs

Have questions?

Here’s what most guests want to know before they book, from licenses and weather, to what to bring and what we're catching.

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How many people can we bring on a charter?

Offshore trips on the 39’ Contender accommodate up to 6 guests. Inshore trips on the 24’ Shallow Sport are best for up to 5 guests due to space and comfort on the flats.

Do we need a fishing license?

No — your license is included. All required fishing permits are covered under the captain’s charter credentials.

What do we need to bring?

Sunscreen, snacks, drinks beyond water, light layers, and a camera. Everything related to fishing — rods, reels, tackle, bait, and ice — is already on board.

Is this trip good for kids or beginners?

Yes. Inshore charters are especially well-suited for kids and first-time anglers thanks to the calm water and steady action. Offshore trips are also great for families who want a full blue-water experience.

Can we keep our catch?

Yes — within state regulations. The captain will explain what’s legal to harvest and will fillet and bag anything kept at the end of the trip.

What’s the best time of year to fish Islamorada?

There’s good fishing year-round, but each season has its highlights. For a month-by-month breakdown, visit our Fishing Calendar.

‍See What’s Biting →

What happens if the weather looks bad?

Safety comes first. If the conditions aren’t suitable, the captain will reschedule or cancel with a full refund. We monitor the forecast and communicate clearly before and during your trip.

Our blog

Lines & Lessons from the Guru

April Fishing Report: What's Biting in Islamorada

April is one of the best months on the water in Islamorada. Here's what we're seeing offshore and in the backcountry this spring.

Fishing Report
Apr 3, 2026

Fishing Charters Departing from Angler House Marina in Islamorada

Convenient backcountry access from Safe Harbor Angler House in the heart of Islamorada.

Guides
Feb 27, 2026

What’s Biting in Islamorada? A Month-by-Month Guide to Florida Keys Fishing

Month-by-month guide to what’s biting in Islamorada. Learn the best seasons for sailfish, mahi, tuna, snapper, and more in the Florida Keys.

Fishing Report
Nov 21, 2025
Read the Fishing Reports
Angler holding a large redfish on a charter boat with the ocean horizon behind him at golden hour
Man wearing sunglasses and a cap giving thumbs up next to a large fish hanging in front of a white boat docked in a marina.
A mint green and white flats fishing boat floating on clear green water under a blue sky with scattered clouds.
Man wearing sunglasses and a cap holding a large fish on a boat with ocean and clear blue sky background.
A couple standing on the bow platform of a flats boat, each holding a redfish they caught, with calm shallow water and puffy clouds behind them

Testimonial section

“We had a great time and caught so many fish! Captain Dylan and his brother Ryan we wonderful and informative. Even though the boating conditions were not perfect, they made it happen..”

“Captain Pete was great. We had a blast. Caught a ton of fish..”

“Great day with captain pete. Had us on the fish all day while the children out fished the adults catching the bigger trout. 10/10 would recommend booking them if you are down here.”

THREE WATERS MARINA (OFFSHORE)

ANGLER HOUSE MARINA (INSHORE)