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!
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. 
Bonefish are a very sought after sportfish in the Florida Keys
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.


Key West is known for big permit and for good reason!

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.


Cooler weather patterns are upon us here in Key West and the Lower Keys. With this change in weather we are greeted with a change in fishing conditions. As a matter of fact, the wintertime here in Key West is one of the best fishing seasons to just “get the rod bent”. The cooler weather brings a bunch of different species of fish into the backcountry off of Key West. There are a bunch of jacks that move onto the flats and into the channels and our barracuda fishing is at its peak as well. Our shark fishing is still consistent 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. 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

—Winter 2019—

This is the time of year when the big barracudas get up on the flats. They are a blast to target on both spinning and fly gear.

There are still some permit and bonefish up on the flats on warmer days.

Tarpon fishing can be pretty tough due to the cooler weather. But ask about our nighttime tarpon trips if you really want to hook into the silver king.

 For those of you just looking to get the rod bent this is one of the best times of year to just go out there and catch a bunch of fish (jacks, trout, snappers, barracuda, sharks, etc)

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