Islamorada · FL · US
Fish the Florida Keys and Everglades with Moon Cast Anglers. Captain Josh Checkeroski offers expert fly and light-tackle charters for tarpon, permit, bonefish, snook, and more, tailored to all skill levels.

At a Glance
Islamorada anchors the middle Keys, a 30-mile stretch of limestone islands and shallow water between Miami and Key West. The town sits at the convergence of the Atlantic Ocean and the Gulf of Mexico, creating distinct fishing zones that shift with season and tide. The flats—vast expanses of 1 to 4 feet of clear water—are the signature draw. Bonefish work the sandy bottom year-round, most abundant in spring and fall. Permit cruise the deeper flats and channel edges, particularly around structure like mangrove roots and coral heads; summer and fall offer the best light and water clarity for sight-casting. Tarpon are the marquee species, with two distinct seasons: spring (March through May) brings migratory fish moving through channels and passes, while summer residents hold in deeper holes and creeks through September. Dry-fly and popper fishing for tarpon in skinny water defines the Islamorada experience, though live-bait chunking and streamer work are equally effective in channels. The backcountry—a maze of mangrove-lined creeks and shallow basins—holds redfish, snapper, and permit in a more protected setting. Water clarity and light are critical here; guides pole the flats at dawn, reading the bottom for cruising fish and working structure methodically. The region's tidal range is modest (2 to 3 feet), but tide timing is essential—incoming water pushes fish onto the flats, while outgoing concentrates them in channels. Summer brings heat and afternoon thunderstorms but also calmer mornings and fewer crowds. Winter (November through February) offers cooler conditions and stable weather, though water clarity can drop after cold fronts. Islamorada's proximity to deep water—the continental shelf drops sharply a few miles offshore—means guides can pivot to offshore species (wahoo, kingfish, mahi) if flats conditions deteriorate. The town itself is well-established, with numerous charter operations, tackle shops, and accommodations catering to anglers of all skill levels.
Location
Islamorada, FL, US
Approximate location
Species & Seasons
Methods
My guiding year in the Florida Keys and Everglades is a dynamic dance with the tides and the seasons, offering something special year-round. While the \
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