Sight fishing for cobia is hard no way around it. It has humbled me. It is such a different game than fly fishing them in the chum slick. The early cobia season as a rule they will not respond to chum—the first big push of cob have one thing on their mind and that is getting to the Chesapeake Bay for their spawn. In June and later the fish seem to respond to chum.
First you have find a cobia swimming on the top and position the boat for your angler to get a cast. Good casters win more often as 60 to 90 foot casts are better than a shorter one. Often when the fish get close to the boat they will spook. So a long cast will give the cobia time to chase and hopefully eat your fly. Boat with towers are much more successful at finding fish much farther away from the boat. This gives their anglers a lot more time to see the fish and plan the cast. Vertically challenged boats like Flat Out it is much more of a speed game as we see the fish closer and have to react quicker.
We have had some inquires about what flies we fish for cobia. My first answer is good question! Over the years our go to fly is a Popovics’s modified Hollow Fly tied in yellow and red. This year we had success with more orange and burnt orange flies. Any fly has to be light enough to cast easily but again push some water and pulse when it is twitched. Being able to adjust your strip to the reaction of the fish helps. In other words knowing how to wiggle the worm. JUST BECAUSE THEY ATE THE FLY ONE DAY DOES’T MEAN THEY WILL THE NEXT DAY! So it is wise to stock plenty of flies with many color variations.
Tackle is basically your albie tackle. RIO’s Tropical or InTouch Out Bound Short Intermediate fly lines are perfect. They load the rod quick and will launch the fly. This year we have been fishing Sage’s Salt HDs 9 or 10 wts. These are easy casting power house rods. Any high quality reel with work but we have been using Sage’s Spectrum Max with to us is the best reel on the market for the price. The other reel we are using is the Seigler MFC and BFC, these reels are fish cripplers. The leaders we fish are 7 to 10 feet 20 pound with 25 to 30 pound fluorocarbon shock tippet.
The more I sight fish for these animals the more I realize I don’t know squat. 
