This thesis explores the relevance of the grotto as an architectural type through time and will propose design possibilities for continuing this tradition in the twenty first century. Specifically, it investigates grotto works from the classical period through the twentieth century. Emphasis will be placed on the form, meaning, and purpose of the grotto as an underground chamber or passage. This thesis also considers the grotto as a platform for theoretical speculation on the implications of designing below the earths surface. The final component of the thesis is a design application comprised of three stories with corresponding collages that portray the design process for grotto inspired structures.