If you're serious about flats fishing, particularly with a fly rod, Captain Nick at Tailing Water Expeditions has earned a perfect 5.0-star rating from 31 Google reviews. Operating 24/7 from 5950 Peninsular Avenue in Key West, he specializes in sight-fishing for the species that make the Florida Keys famous: tarpon, permit, and bonefish.
According to customer reviews and his website at tailingwaterexpeditions.com, Captain Nick focuses on technical flats fishing rather than the high-volume reef action many Key West guides offer. This is a different style of fishing that requires patience, good casting, and often results in fewer fish but more memorable catches.
You can reach him at (305) 407-7064. The 24/7 availability suggests flexible scheduling, which matters when you're targeting species that feed based on tide and light conditions rather than clock time.
Fly fishing expertise and teaching
Captain Nick works with anglers who have decades of freshwater fly fishing experience but are new to saltwater. George Fleszar and a friend, both longtime trout anglers, specifically praised Nick's ability to put novice saltwater fly fishers onto fish and teach technique during the trip.
Mission-oriented guiding
When Christina Tagliani didn't connect with a permit on her first trip, Nick made it his mission a year later to get her that fish. "Running from storms and chasing the sun," he worked to find the right spot and coached her through what she called a "nail-biting but rewarding adventure." That's commitment to your client's goals.
Hard-charging style with good teaching
Jesse Smith called Nick "a hard charger who loves what he does" and noted his willingness to teach. For guides who chase technical species like permit, that combination of hustle and instruction matters.
With 31 reviews and a perfect 5.0-star rating on Google, the feedback consistently highlights:
Teaching ability and patience. Multiple reviewers mention Nick's skill at coaching through difficult presentations and keeping spirits up during the inevitable slow periods that come with flats fishing.
Species knowledge. Reviews reference putting clients on bonefish, permit, tarpon, and multiple other species. Nick clearly knows where these fish move and how to position anglers for shots.
Willingness to work hard for his clients. The story of running from storms and chasing sun to find permit shows he doesn't just sit in one spot hoping fish show up.
Positive demeanor. Words like "fun," "friendly," and "fantastic" appear throughout reviews, which matters when you're spending hours poling around flats where the fish don't always cooperate.
The main thing to understand is this isn't high-volume action fishing. Sight-fishing for permit and tarpon means long periods of searching, brief windows of opportunity, and the very real possibility of going 0-for-1 despite solid shots. Reviews suggest Nick prepares clients for this reality while working to make it happen.
Fly anglers who want to level up their saltwater skills - If you've got freshwater fly fishing dialed in and want to tackle permit, tarpon, or bonefish with proper technique, Nick gets strong reviews for coaching through the transition.
Anglers targeting specific species - When you're coming to Key West specifically to chase permit or tarpon rather than just "catch fish," this focused approach makes sense.
Patients anglers who value quality over quantity - If you'd rather have one shot at a 20-pound permit than catch 30 yellowtail snappers, you're Nick's kind of client.
Multi-species sight-fishing fans - Reviews mention bonefish, permit, tarpon, and other species, suggesting Nick moves around to find whatever's feeding rather than focusing exclusively on one target.
Be honest about your casting ability when you book. Flats fishing requires accurate casts of 40-60 feet, often with wind. If you're still working on distance or accuracy, mention that so Nick can position you better or suggest working on other species first.
Bring polarized sunglasses with quality lenses. You're sight-fishing, which means spotting fish before you cast. Cheap polarized glasses won't cut it. Copper or amber lenses work well in the Keys backcountry.
Understand the permit reality before you go. They're called "the fish of 10,000 casts" for a reason. Even with an excellent guide, you may not hook one. If that will ruin your trip, consider targeting the more cooperative bonefish instead.
Ask about tide timing when you book. Many flats species feed best on specific tide stages. Nick's 24/7 availability suggests he'll work with tide windows rather than forcing you into a bad timing.
Practice your double haul before the trip if you're fly fishing. Wind is common in the Keys, and being able to punch a fly through it makes a massive difference in your hookup opportunities.
Listen when Nick tells you to wait on your cast. With permit especially, one bad cast can spook the whole school. Better to have patience for the right shot than blow it by rushing.
Source: Google My Business listing and customer reviews for Tailing Water Expeditions, accessed January 2026.
