By: Alex Baumann

Long before modern skiffs and fly tackle, anglers were drawn to this region in pursuit of the Silver King. In the late 1800s and early 1900s, tarpon fishing here became a national sensation, attracting prominent figures from across the country. Among them was Theodore Roosevelt who frequented Southwest Florida and helped cement the area’s reputation as a premier sporting destination. Cabbage Key along with nearby Useppa Island became a hub for early tarpon anglers, where stories of hundred-pound fish and long battles were forged in the surrounding waters of the Sound.
The difference now is pressure. Boca Grande is known as the tarpon capital for a reason but it can get crowded and technical especially in May. Just a short run away Pine Island Sound offers a completely different experience. There is more room to move, fish are less pressured and it sets up perfectly for fly anglers who want to hunt rather than sit in a line of boats.
Fishing around the sound in May is all about paying attention. Early in the morning you will find fish rolling along channel edges and deeper cuts. Setting up ahead of them and making a clean shot is key. Most days a floating or intermediate line with a longer leader gets the job done. Simple patterns like toads, cockroaches, and baitfish flies are all you really need if you put them in the right place.
The beaches are another huge part of the program. Fish cruise just off the sand from Sanibel up past Cayo Costa and they are usually moving steady. If the light is right you can see them from a long way off and set up for a clean presentation. These fish are often more relaxed than what you find in the pass which makes it a perfect scenario for fly fishing.
Inside the Sound focus on moving water and areas where bait stacks up. Cuts between islands, troughs near the Intracoastal and any kind of edge will hold fish. They might not be packed together but they are there and they are catchable if you stay patient and keep looking. What makes this place stand out is the mix of history and opportunity. You are fishing the same water that guys were fishing over a hundred years ago and it still produces in a big way. For anyone willing to explore a little bit, Pine Island Sound in May is one of the most underrated tarpon fisheries out there.