Much attention on nearby Phoenix’s development has almost eclipsed Tucson’s long history of becoming a great sunbelt city. Phoenix’s predominance appears to be more of the same decades-old growth machine, and less of what is important: Livable quality of life. Tucson’s southwestern location, scale and built heritage may have worked to its advantage and current quality of urban life. This chapter explores the following research question: Are there any lessons to be learned from Tucson’s recent urban revitalization efforts? The purpose of this chapter is to reflect on Tucson’s urban and regional transformations and to extract a set of lessons learned that can be useful to other cities similar to Tucson. The argument is that although Tucson may have had difficulty obtaining funding and attracting investment prior to the 2007–08 global financial crisis, from a quality of life perspective Tucson’s residents appear to benefit from a whole array of small- and medium-size town amenities such as a compact and exciting downtown, affordable housing, alternative modes of transport, cultural institutions, a vibrant arts and culture scene, a land grant university and proximity to protected desert natural environments. A framework for analysing quality of life and livability is presented.