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.
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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.
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
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.
'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
6 guests
'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
5 guests
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
6 guests
Inshore - Back Country
Target Species
What we're catching in Islamorada
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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
Private Group Fishing Charters
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.
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.
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
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.”
