India, Feb. 13 -- The Milano Cortina Winter Olympics are the most geographically spread out Winter Games in history, unfolding across 8,500 square miles of Northern Italy and the Dolomites. Rather than concentrating in a single host city, the competitions weave through alpine valleys, lakeside towns, the urban heartbeats of Verona and Milan, and some of the most breathtaking and iconic ski and snowboard terrains in the world. The 15 official Olympic venues are scattered across seven clusters. Instead of one Olympic Village, there are six.

To make sense of this logistical pretzel, Milano Cortina organizers created a transportation app that lets users plug in any two Olympic venues and generate an optimal route. In a landscape of road clos...