About Your Guide

Dylan McClaugherty

Outfitter
Captain Dylan and his team invite you to experience the incredible variety of fishing that makes Islamorada one of the most celebrated destinations in the Florida Keys. Alongside Dylan, the team includes Captains Travis and Peter, experienced inshore captains who help cover the backcountry, flats, and surrounding waters of Islamorada.

These guys spend their time fishing the local waters and understand that a successful day starts with being flexible. Tides, currents, bait movement, water color, weather, and the season all play a role in determining where they'll fish and what they'll target. Instead of sticking to the same routine every day, the crew builds each trip around what's happening on the water.

Their trips cover everything from shallow backcountry and Florida Bay fishing to reef fishing and offshore runs into blue water. Depending on the adventure you choose, you might find yourself casting around mangroves for Snook and Tarpon, working the flats for Redfish and Trout, dropping baits over a productive reef for Snapper and Grouper, or heading offshore in search of Mahi Mahi, Tuna, Sailfish, and Wahoo.

The fleet...

About Your Guide

Dylan McClaugherty

Outfitter
Captain Dylan and his team invite you to experience the incredible variety of fishing that makes Islamorada one of the most celebrated destinations in the Florida Keys. Alongside Dylan, the team includes Captains Travis and Peter, experienced inshore captains who help cover the backcountry, flats, and surrounding waters of Islamorada.

These guys spend their time fishing the local waters and understand that a successful day starts with being flexible. Tides, currents, bait movement, water color, weather, and the season all play a role in determining where they'll fish and what they'll target. Instead of sticking to the same routine every day, the crew builds each trip around what's happening on the water.

Their trips cover everything from shallow backcountry and Florida Bay fishing to reef fishing and offshore runs into blue water. Depending on the adventure you choose, you might find yourself casting around mangroves for Snook and Tarpon, working the flats for Redfish and Trout, dropping baits over a productive reef for Snapper and Grouper, or heading offshore in search of Mahi Mahi, Tuna, Sailfish, and Wahoo.

The fleet
gives Dylan, Travis, and Peter plenty of flexibility. Their 26' Pathfinder is a versatile hybrid bay boat capable of working shallow backcountry water or heading offshore, while the 39' Contender provides the speed, space, and offshore capability needed for serious reef and deep-sea fishing.

Most importantly, Dylan and the crew want the experience to fit the anglers onboard. Whether you're an experienced fisherman looking to chase a specific species, bringing the family out for a fun day, or wetting a line in the Florida Keys for the first time, they'll work to make your time on the water comfortable, engaging, and memorable.
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A Fishing Guru Trips

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Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

Offshore Deep Sea Fishing - 39'

NEW
39 ft 1 - 6 People From $1,300
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Islamorada

Inshore Backcountry Fishing

NEW
26 ft 1 - 5 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Islamorada

4-8 Hour Trip – Offshore 26'

NEW
26 ft 1 - 5 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Islamorada

Reef Fishing

NEW
39 ft 1 - 6 People From $1,000

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Potential Target Species

Color-coded seasonality below is based on .
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

A Fishing Guru Photo Gallery

Inshore Backcountry Fishing
September 1st, 2026
Islamorada, Florida
Offshore Deep Sea Fishing - 39'
September 1st, 2026
Islamorada, Florida
Reef Fishing
September 1st, 2026
Islamorada, Florida
4-8 Hour Trip – Offshore 26'
September 1st, 2026
Islamorada, Florida
Inshore Backcountry Fishing
September 1st, 2026
Islamorada, Florida
Offshore Deep Sea Fishing - 39'
September 1st, 2026
Islamorada, Florida
4-8 Hour Trip – Offshore 26'
September 1st, 2026
Islamorada, Florida
Reef Fishing
September 1st, 2026
Islamorada, Florida
Offshore Deep Sea Fishing - 39'
September 1st, 2026
Islamorada, Florida
Inshore Backcountry Fishing
September 1st, 2026
Islamorada, Florida
4-8 Hour Trip – Offshore 26'
September 1st, 2026
Islamorada, Florida
Reef Fishing
September 1st, 2026
Islamorada, Florida
Reef Fishing
September 1st, 2026
Islamorada, Florida
4-8 Hour Trip – Offshore 26'
September 1st, 2026
Islamorada, Florida
Inshore Backcountry Fishing
September 1st, 2026
Islamorada, Florida
Offshore Deep Sea Fishing - 39'
September 1st, 2026
Islamorada, Florida
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