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.

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.


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. 


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.


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.





Cooler weather patterns are on their way to the backcountry in Key West and the Lower Keys. With this change in weather we are greeted with a change in fishing conditions. There are a ton of fish that are willing to pull some drag and bend the rod during the cooler months. As a matter of fact the wintertime here in Key West is one of the best fishing seasons to just pull on some fish. There are a bunch of jacks that move onto the flats and into the channels. Barracuda fishing is at its peak as well. Our shark fishing is still strong and the snapper fishing can be fantastic.

 Our sport fishing can become more challenging with the cooler water up on the flats along with some windier days. But we can still find plenty of permit and bonefish up in the shallows during nicer weather patterns but don’t expect to knock it out of the park if your fishing trip falls during a cold front.. Most of the big tarpon have left the backcountry but we still have a population of our juvenile residential tarpon (10-20lbs) that are almost always willing to play ball. If you are coming down to here and desperately want to hook into the silver king be sure to ask about our Key West Night Fishing for Tarpon. They are nocturnal fish and can be readly found gorging on shrimp and baitfish under the moonlight. 

Give us a call and set up your fishing adventure today!


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

1) There are still plenty of bonefish and permit up on the flats as the cooler weather approaches.

2) Tarpon fishing is still consistent with juvenile fish (10-20lbs) in the Backcountry.

3) Our “rod bender” trips are a lot of fun with a big push of fish like jacks, snapper, sharks and barracudas coming in the backcountry.

4) If you really want to hook into the silver king make sure to ask about night fishing for tarpon. They are a nocturnal species and you can really do some damage under the moonlight.

Fall Fishing in Key West

Key West Fishing Report Time is just flying by and the fall fishing season is already upon us here in the Florida Keys. We may not have a pile of colorful leaves in the backyard,

Read More »

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.

Read More »

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.

Read More »