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. 


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. 

Flats Fishing in the Florida Keys has been an obsession angler have enjoyed for generations. This legendary fishery is home to many inshore world records on both fly and spinning gear. Thousands of monstertarponmigrate 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 differentfish specieshere 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 ever-changing. Take a peek at our fishing seasons calendar for an idea of what is biting certain times of the year 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: Winter 2020

“Key West Winter” is here, and everything is falling into place. The shallow flats and backcountry around Key West are filling in with our cold-water species like jacks, barracuda, snapper, sharks, and many more. Winter season is hands down the best time of year to come out and get the drag screaming while catching a wide variety of species.

Due to the late and warm beginning of winter, our flats fishing for permit and bonefish has still been very consistent, given a bit of sunshine and clear water. We have been catching tarpon on live bait, but the cooler weather hasn’t made it easy to throw flies at them.

As far asfly fishing goes, we have been having a lot of fun throwing at all types of species; up on the flats and in deeper water, and depending on the weather conditions. The wintertime is famous for being the best time of year to target large barracudas in the shallows. They are a lot more challenging to trick than you would think. Jacks are also in town and an absolute blast to fight on a fly rod.

On warm days the shallows have been full of bonefish, permit, and tarpon, both big and small. For a more in-depth look, check out our complete Winter Fishing Report.”


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.