John’s Pass separates Treasure Island from Madeira Beach and it’s here you’ll find the greatest concentration of fishing and boating charters. On the Madeira Beach side, assembles the salty shopping and dining district of John’s Pass Village & Boardwalk. It’s a good place to hoist a beer and swap fish tales or enjoy the fruits of John’s Pass’ reputation for grouper catches. Clock in during October for the annual John’s Pass Seafood Festival.