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. 

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.

WHAT'S BITING NOW: Fall/Winter 2021-2022

As the conditions start to change we are also seeing a change in the fishing. Our summertime species are reacting to the cooler water temperatures and starting to thin out. At the same time our winter time species are beginning to load up the backcountry. With the variety of life and bait that is coming inshore, all of the predators are following suit. Jacks, barracuda, snapper, grouper, sharks and many more will continue to fill in as the next couple months and weeks go by. 

Don’t fret we will still be able to find some permit, bonefish and tarpon during these cooler months. But keep in mind that the cooler the conditions, the more difficult it will be to find these three up on the flats. Targeting large barracudas in the shallows is a great way to spend these cooler days. We also have jacks, snapper, sharks and plenty of other species we can sight fish for on both spin and fly fishing gear.

Look forward to some rod bending and drag screaming action through these next couple months. Feel free to reach out if you have any questions in regards to booking a trip! 


Fall/Winter Fishing Report

Fall/Winter Fishing Report It seems that the long hot summer days are coming to an end down here in Key West and the Lower Keys. I have to admit as much as I will miss

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Spring Fishing Report

Spring Fishing Report Big Tarpon It’s starting to heat up down here in the Keys and so is the fishing. We are starting to see our first waves of big migratory tarpon. They are filling

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Winter Fishing Report

Winter Fishing Report So our “Key West Winter” is finally upon us and I have to tell you that this is one of the warmest seasons I have ever seen. So far anyway. We have

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Opened in 2009, we are a fly shop located in Key West, Florida. It is our intention to be at the leading edge of fly fishing in the Florida Keys.