Guided by Josh Checkeroski
Located in Islamorada, Florida, Captain Josh offers fly fishing and light tackle fishing charters for Tarpon, Bonefish, Permit, Snook, Redfish, Jack Crevalle, Snapper, and more!
Whether on the hunt to catch as many Florida Keys species as possible, or focused on stalking Permit on the flats, Captain Josh looks forward to sharing this world-class fishery with you.
Captain Josh's fly fishing guiding career spans over 10 years and multiple diverse geographies. Excellent with beginners and experts alike, Captain Josh has seen it all.
From guiding for Salmon and Steelhead in Michigan, to catching Brown Trout and Rainbow Trout in the Grand Tetons of Wyoming, to the breathtaking saltwater species of the Florida Keys, Josh's infatuation with the journey is what keeps him on his toes. He is a student of the sport, and enjoys teaching anglers how to cast and present flies as much as he enjoys watching anglers set the hook, fight the fish, capture the picture, and the release.
From casting artificial lures at Snook and Speckled Trout to targeting Permit, Bonefish, and Tarpon on the fly, Captain Josh looks forward to providing the gear, knowledge, experience, and passion necessary for a fantastic day fishing the Florida Keys.
Fill in date, party size, trip duration, and start time above to book and get out there with Captain Experiences and Captain Josh out of Islamorada, Florida!
Head out with Captain Josh for an action-packed day of fly fishing in the Islamorada flats! The inshore flats in this world-famous fishing hotspot provide excellent year round fishing for a host of sought-after species. Let Captain Josh show you why fly fishers from all over flock to this fishing paradise! On this 4 to 8-hour trip, Captain Josh will take you into the beautiful Islamorada backcountry flats where you'll be fly fishing for sought-after fish including Barracuda, Black Drum, Bonefish, Jack Crevalle, Permit, Redfish, Snook, and Tarpon. Although many of these elusive fish require some pretty accurate casting, Captain Josh is happy to help anglers of any skill level and will provide expert-level instruction to accommodate you and guests! You'll be aboard a 17' Maverick HPX-V skiff boat with capacity for 2 anglers. Powered by a 90 HP Mercury engine, this boat was designed with shallow waters in mind and she'll have no problem letting you creep up on even the most skittish fish. It comes equipped with GPS, Fishfinder, a Live Bait Well, a Wireless Trolling Motor, and an Ice Box to store your catches. Captain Josh will provide all rods, reels, tackle and fishing licenses. All you need to bring is sunglasses, sunscreen, and any food or drinks you might need. Come aboard with Captain Josh and see what all the Islamorada buzz is about! Read More
Josh took my 14-year-old son (Bill) and me out for a day of backcountry fishing. We had an awesome time and caught a lot of fish and one very large Jack. He knows his staff has great boat/equipment and is highly recommended. I plan on fishing with him again! …
It was a great day on the waters with Capt. Josh. He made the whole experience great. He knows the back country waters really well and put me on multiple species of fish. He really puts the client first and tailors the experience to their desired outcome while providing guidance and tips to make you a better angler. Also, a great conversationalist and enjoyed swapping stories throughout the day. …
My wife and I had an awesome experience fishing and exploring the Everglades with Josh. My experience is small river/stream fly fishing. Josh made the transition to saltwater fun and educational. We look forward to fishing with him again.
Captain Josh took us fishing in the Everglades. He is an obvious Type A and was highly motivated to make sure the trip was a success. He knows the water and fish extremely well and was dead accurate on where the fish were and how to catch them. He has a great personality and we felt very lucky to have the opportunity to fish with him. My only complaint is the 8 hour day flew by because we were having so much fun. …
We had a great start to the day with some early action and a nice redfish in the boat (see photo) but then the weather and conditions turned against us. Despite that Capt Josh worked really hard to find fish, was great company and we had a super day. I would definitely recommend Capt Josh and will fish with him when I come back to the Keys. …
I’ve known the captain from my time out West where he outperformed others in the fresh. In heading to the Florida Bay with the kids for a day, I made the call and with no hesitation Josh customized my day to maximize the good times. Showed up promptly, clean boat, great attitude and we proceeded to be in nonstop action for the entire time. His passion for the Florida Bay and the greater Everglades was clearly evident when spending the day with him. With all the choices of guides out there, you can’t go wrong with Josh!! …
Having fished with Capt. Josh over the last five years between Florida, Idaho, and Mexico, I have come to know him as a hardworking guide and friend. Each time I step in his boat I’m always impressed with his level of professionalism and determination to make the most out of every minute of every trip. My last trip was no different as we chose different fishing locations throughout the week based on weather and tides. While Josh prefers to target fish on the fly he rarely turns down the opportunity to throw conventional tackle when the conditions suggest. Although I was originally reluctant to “spin fish” on a windy overcast day with less than ideal tides, we managed to jump multiple tarpon and bring a handful of snook to hand by being versatile and leaving my ego at the dock. This is just one example of Josh’s unique ability to find fish when other guides are struggling to find them. …
Barracuda, Black Drum, Bonefish, Jack Crevalle, Permit, Redfish, Snook, Tarpon
211 Wildwood Cir, Key Largo, FL 33037, United States | Bodies of water fished: Islamorada Underwater Coral Gardens, Duck Key, Key Largo