with Capt. Nick LaBadie

Welcome to Tailing Water Expeditions. A premier guide service based out of beautiful Key West, FL. We provide 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. 

and 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!
this picture is taken right at water level of a Florida keys redfish ready for release into the clear backcountry waters.
Beautiful mangrove islands and crystal clear flats pave the way to an incredible adventure. The backcountry off of Key West is full of non-stop rod bending action and fun for everyone!
Cool jump shot of a fun size tarpon hooked in Key West, Florida
The Marquesas Keys are home to a world class fishery. Everything from renown flats fishing to an epic reef line are just around the corner. It is the wild west of Lower Keys fishing and anything can happen.


Key West is home to a plethora of targeted gamefish fishing opportunities. Florida itself is dubbed as the “Fishing Capital of the World”, and it is this specific area of Florida that houses nearly 1,000 square miles of interconnected basins, grassy mud banks, and mangrove islands in its estuary system. The estuary is where these popular gamefish spawn and reproduce. Combine this with nearby reefs, waterways, and direct ocean access on both coasts – and you will find yourself in the heart of Florida fishing. Below we have listed our most popular species as chosen by our clients, but this is just the tip of the iceberg: See All Species for more information.

We get some monster tarpon here in the Florida Keys!
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. 
A close up picture of nick labadie holding a beautiful lower keys bonefish caught on fly on a clear backcountry flat with blue skies and mangrove islands in the background.
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.
An angler is holding up a beautiful thirty plus pound permit caught in the backcountry off of key west.
The Florida Keys are known for sight fishing these shallow water gamefish and for good reason. They are arguably one of the most difficult and impressive fish to catch on the flats - in the world.


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.

There is a big playground out there and the conditions are always 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.


The Florida Keys are one of the worlds top fly fishing destinations. 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.

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


Well it is summertime here in the beautiful Florida Keys and without a doubt one of my favorite times of year to be out on the water. Temperatures warm up and so does the sport fishing. First and foremost, tarpon are still here in great numbers and are a blast to target on light tackle spinning gear. If you are into fly fishing, it is hard to beat the summertime fishery here in Key West. The winds are light and the sight fishing is off the chain!

Permit fishing is in full swing with a lot of fish up on the flats around Key West and the Marquesas Keys. The typical calm beautiful days this time of year make spotting these fish a blast in the shallows. Bonefish season is here ladies and gentlemen. The grey ghosts are crawling all over the flats and eager to play ball. Bonefish are a lot of fun to catch on BOTH spinning rods and fly fishing gear! With the waters warming up there are still some snapper, jacks, and barracuda swimming around the backcountry to fill in our rod bending trips. And don’t count out the the shark fishing!

Latest Key West Fishing Report!

an angler poses with a juvinile tarpon over the crystal clear waters of the lower keys backcountry

1) The baby tarpon are biting! Late summer & fall is my favorite time of year to target our “fun sized” tarpon (10-30lbs)

2) This is also a great time of year to chase after permit and bonefish on the flats.

3) If you are just wanting to bend the rod make sure to ask about night fishing for tarpon. They are a nocturnal species and you can really hook a lot of fish under the moonlight.

4) Lobster season is in full swing as well. You get 6 per person and if you have never been lobstering here in the Florida Keys it is a must do!

August Fishing Report

Key West Fishing Report August Fishing Report We are officially smack dab in the middle of one of my favorite times of year to get out on the water here in the beautiful Florida Keys.

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June Fishing Report

Key West Fishing Report June Fishing Report I am in love with the summertime here in the Florida Keys. As soon as June rolls around it’s just fun and games for the next couple months.

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May Fishing Report

Key West Fishing Report May Fishing Report   As to be expected tarpon season is in full swing here in the Florida Keys. There are fish all over the place both migrating the ocean side

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Our Featured Boating Charters In The Keys

Our boating charters are a great way to beat the heat and enjoy the waters off the coast of Key West. Whether taking a snorkeling trip to amazing and hidden locations, filling up on seasonal lobster, or mixing it up with a combo that includes fishing – these trips can be just what the doctor ordered for your next Key West vacation.


Coral formations off of key west offer great snorkeling and are home to an abundance of fish species.
Snorkel the pristine waters of the Florida Keys on a private charter with a experienced guide that can take you places commercial boats cant. Snorkeling Gear is provided.


A happy family lays out their pile of freshly caught Florida keys lobster.
Winner winner lobster dinner! Dive on in and grab yourself some fresh Florida Keys lobster. Gear and instruction is provided. Limit is 6 lobster per person during lobster season.


Can't choose between fishing and snorkeling? Come on then lets hit the water for a combo trip with a little bit of both worlds. Spend some time under the water and some laid back fun fishing.