Yellowtail snapper is a chumming game on the reef edge, and it is one of the most reliable coolers in the Keys. Brian works patch reefs out of Key Largo; the dedicated reef trips run on the family's boats out of Islamorada.
Yellowtail are caught in a chum slick, not by casting around. You anchor up-current of the reef, get a slick going, and feed baits back on light leader until the fish come up in the water column. It is patient, technical fishing, and when it works you fill a cooler with the best-eating fish in the Keys.
His reef work is the patch reefs and channels: mangrove snapper, Spanish mackerel in the cooler months, and whatever else comes through on light tackle. It is shallower, closer, and a great half day. Yellowtail show up there, but the numbers live on the reef line proper.
For a full-on yellowtail trip, the family fleet runs it out of Islamorada on the Poppa Bay, a 25 foot Sea Hunt set up for exactly this, and on the bigger boats when the group is larger. Their yellowtail page is here.
Captain Key Largo and The Poppa Wahoo Collective are the same family. Call either one and you get pointed at the boat that fits the trip, not the boat that happens to be free.
You can pick them up on the patch reefs, yes. For a dedicated chumming trip on the reef line, the family's Islamorada boats are set up for it.
They are widely considered the best eating fish in the Keys, and any of the captains will clean and bag them for you.
Year-round. There is no bad month for yellowtail.
About twenty minutes south of Key Largo on US-1.
Captain Key Largo runs the backcountry, the flats and the reef out of Key Largo. The Poppa Wahoo Collective runs the offshore fleet out of Islamorada. Brian will put you on whichever one fits the trip.