While management of cross-border tourism destinations has been of considerable interest to policy makers and tourism scholars for a long time, less attention has been given to Asian tourism destinations. A region well known worldwide is the Golden Triangle which shares its borders with Laos, Thailand and Myanmar. This chapter identifies key tourism planning issues, through interviews and a survey of key stakeholders, faced by a small town on the Thai side of the border – Chiang Saen. This tourist destination in Thailand draws local and international tourists because of its proximity to the Golden Triangle. Four broad issues restricting tourism development for Chiang Saen were identified: a complex web of stakeholders, powerful vested interests, a lack of identity or planning direction, and weak market attractiveness. Core Thai values of fatalism, relationship building, harmony and hierarchy contribute to the existence of these planning issues and constrain problem resolution. Furthermore, western style recommendations for planning development are likely to be ineffective. However, suggestions that leverage Thai values have potential to assist local tourism planning.