Mobile wayfinding and guide apps have become indispensable tools for navigating unfamiliar urban spaces. Such applications address targeted, "just-in-time" queries, but are not optimally designed for multi-point expeditions that can quickly build route and survey-level familiarity with a neighbourhood. We first conducted an experimental simulation involving a homebuying scenario to assess the usefulness of a popular mobile wayfinding and search application (Google Maps) for exploring a neighbourhood. We then designed a prototype application called Block Party that addresses a number of limitations of Google Maps for this purpose, and evaluated it in a second replica study. The results suggested that application designs that facilitate switching among distinct but synchronized navigation views such as Block Party might support more efficient usage and the selection of task-appropriate views, leading to better overall spatial awareness.