Using modern technology to examine classical mathematics problems at the high school level can reduce difficult computations and encourage generalizations. When teachers combine historical context with access to technology, they challenge advanced students to think deeply, spark interest in students whose primary interest is not mathematics, and encourage novices to delve into higher mathematics at a pace and level at which they can succeed. Geometry naturally lends itself to making connections through classical mathematics. An activity that originated in the author's advanced geometry class, "Archimedes and pi," entices students to investigate pi geometrically and build understanding by incorporating technology within a historical context. The "Archimedes and pi" activity can help students at varying ability levels extend their knowledge of circumference and perimeter, trigonometry, and the limiting process. Its historical context and use of hands-on technology encourage understanding and help students retain the mathematics concepts. (Contains 9 figures.)