with Capt. Nick LaBadie

Welcome to Tailing Water Expeditions. A premier fishing guide service based out of beautiful Key West, FL. Providing next level inshore, flats, and backcountry fishing trips. As well as other private specialty charters. Top of the line service and equipment pave the way to an experience of a lifetime.


Below you will find the most popular fishing charters for our clients in Key West. These trips are centered inside of the best in local hot spots that Captain Nick has hand picked through his years of experience here. Aside from the fishing, experiencing this fishery is something that one must fully immerse themselves in, these specific trips do just that. So, if you’re looking for epic fishing, an awesome journey, and memories that will last a lifetime – our Featured Fishing Charters fit the bill.

An angler is hooked up to a bonefish with a spinning rod on a clear shallow flat in the Florida keys with the sunshine bright over the sandy shallows and a single green mangrove island in the background
Flats fishing in Key West is truly world class. Sight fishing in the shallows with a fly rod or spinning gear is an experience of a lifetime. Tarpon, bonefish, permit, barracuda and more!
Catching bonefish on fly is a blast and the Florida Keys are one of the best places in the world to do it!
Bonefish are one of the most sought after gamefish in the world. The Florida Keys are known for being home to a number of world record catches. The experience in itself is worth the price of admission.
Here is a nice tarpon jumping in the backcountry off of Key West
Welcome to the addiction. Key West has one of the best tarpon fisheries in the world. Averaging 60+lbs with drag screaming runs and aerial displays, come find out why these are the perfect gamefish. 


Flats Fishing in the Florida Keys has been an obsession anglers have enjoyed for generations. This legendary fishery is home to many inshore world records on both fly and spinning gear. Thousands of monster tarpon migrate up and down the coastline every spring, world class permit fishing flats are just 10 minutes from the dock, and bonefish scurry around the shallows in some of the most stunning areas we have ever witnessed.

We have many different fish species here in the Florida Keys but the Tarpon, Permit, and Bonefish are considered the top three sport fish lurking around in the shallows. We target them with both fly fishing gear as well as spinning rods depending on the conditions and the anglers experience.


Keys West and the Florida Keys are among the worlds top fly fishing destinations. Fly fishing This is not only a past time, but a sport that has been enjoyed by many generations. 

Fly Fishing down here in the Florida Keys has been made famous by a lot of popular fishing personalities, both past and present. They have made the Keys their home for some of the best long rod action on the planet.

Our crystal clear tropical flats offer some of the best sight fishing opportunities in the world. Whether looking for bonefish, permit, tarpon, barracuda, jacks, or snapper on the fly. Tailing Water Expeditions with fly fishing guide Captain Nick LaBadie is your go-to in Key West. 

There is a big playground out there and the conditions are ever changing. Take a peak at our fishing seasons calendar for an idea of what is biting certain times of year in order to maximize your success on the water. We specialize in fishing the flats and backcountry from Big Pine Key to the Marquesas. Sight fishing in the calm clear water is an experience that you will not forget.


We have been having some of the best fall fishing I have ever seen down here in Key West. I think it has a lot to do with not having any cold fronts yet but we aren’t complaining. There are permit absolutely everywhere. It is hard to leave the dock and not stumble across some it has been incredible. The bonefishing has also been very strong with some good size fish out there and some big schools and hungry fish coming through on the flats. The baby tarpon fishing was pretty slow during a couple of the summer months but it is now coming completely unglued. It has been fantastic with a lot of hungry juvenile tarpon up under the bushes and in backcountry channels. Once we start getting some cold weather I’m sure patterns will change but as of now it is on fire.

The “rod bending” species are all starting to show up as well. Jacks, snapper, and big barracudas to name a few, are all filing in their backcountry haunts to set up for the winter time rally. The cooler months always tend to bring in a wide variety of species into the backcountry surrounding Key West and the Lower Keys. 

Tarpon Season dates are starting to fill up. Be sure to book in advance for spring time dates in 2020.


Fall Fishing Report

Fall Fishing Report The cool north breeze has made its way down to Key West in the past couple weeks. And with the change in weather conditions brings a change in the fishery. The water

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Flats Fishing in Key West

What is Flats Fishing? So when someone says they want to go flats fishing they are referring to generally shallow water. Anywhere from a couple inches to a couple feet would classify as being on

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Fly Fishing For Bonefish

Fly Fishing For Bonefish When someone says they are going “bonefishing” in the Keys the first thing I think about is a couple of us quietly floating across a crystal clear flat and the sun

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