Pricing & Availability

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Fishing Info


Fly Fishing

Water Type

Inshore, Nearshore, Flats

Skill Level

Beginner, Intermediate, Advanced


Barracuda, Black Drum, Bonefish, Jack Crevalle, Permit, Redfish, Snook, Tarpon

About Your Boat

Boat type: Skiff

Boat Manufacturer: Maverick HPX-V

Boat length: 17ft

Engine Manufacturer: Yamaha

Engine HP: 90HP

Number of engines: 1

Extras: GPS, Fishfinder, Live Bait Well, Wireless Trolling Motor, Ice Box

About Your Guide

Located in Islamorada, Florida, Captain Josh Checkeroski 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.

Click "See Dates" to Search It, Book It, Live It with Captain Experiences and Captain Josh Checkeroski of Moon Cast Anglers out of Islamorada, Florida!


Jeff V.

December 30, 2019

Having fished with Capt. Checkeroski 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.

Tabetha R.

December 3, 2020

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.

Arg .

February 10, 2020

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 Checkeroski!!



All rods, reels, and tackle are included.


Feel free to enjoy responsibly, but please no glass.


You will get a refund if the trip is canceled due to weather.

Fish Cleaning

No cleaning service provided.

Boat Restroom

No, this boat does not have a bathroom on board.


No meal provided.

Gear & Packing


All Tackle

At an Additional Rate

No added costs.

Recommended Packing

The cooler is filled with bottled water, please bring any other beverages you'd like. Bring sunscreen, SPF clothing, hat, and polarized sunglasses.

Required Items

A valid fishing license.

Things to Keep in Mind

Payment & Tipping

After paying the deposit, a QR Code will be emailed to you. On the day of the trip, your guide will scan your QR code to automatically transfer the remaining balance. The only cash needed is for a 10-20% customary tip.

Cancellation/Refund Policy

Yes, cancel for free up to 14 days before the trip.

Where to Buy a Fishing License

Find a license for your state here.


Start Location

Everglades National Parks Visitor Center, State Highway 9336, Homestead, FL, USA

Start Time(s)

05:00 AM, 06:00 AM, 07:00 AM, 08:00 AM, 09:00 AM, 12:00 PM, 01:00 PM


4 hours, 6 hours, 8 hours,