This is as budgeted as it gets in Key West. Fish the southwest side of the Stock Island to Boca Chica bridge after dark. You can legally fish all along the south side of bridge.. barrier between cars and fishermen. Fish the shadow line with live pilchard or live finger mullet... freelined is best... Tarpon, snook, and monster mangrove snapper. Jumbo live shrimp should work as well if you can find a bait shop that carries any live bait. Twenty lb mono to 40 lb leader will work.
https://goo.gl/maps/xqB4Dzkpt922Should be a couple of head boats in Key West... fun trips but wouldn't count on catching much size wise unless you catch something small enough and use it for live bait on bottom.