Predicting and warning for tornadoes developing near the complex coastline of urban Lee and Charlotte counties in Southwest Florida is often a challenge. The closest NWS radar is 130-180 km to the northwest. Four warm season cases examined from coastal southwest Florida showed striking similarities in tornado development. Southeast flow and Gulf Coast sea breeze development interacted with local topography to create cyclonic mesocirculations. These circulations led to more predictable boundary collisions and enhanced convection with strong updrafts capable of supporting brief tornadoes. Ambient flow and the degree of instability were important factors in the timing of various interactions leading to tornado development. The results of this study should help forecasters identify the patterns conducive to southwest Florida tornado development.