Macao describes a small locality on the south coast of China, a couple of kilometres across the Pearl River Delta from Hong Kong. In history, it has been an important trading port centuries ago and connected to global trading routes long before the term “globalization” was widely used. Based on this legacy, Macao appears to have trade and commerce in its DNA. Locally, the Macao Commercial Code was enacted in 1999 largely based on the influence of comparative law and legal pluralism. Globally, Macao joined the General Agreement on Tariffs and Trade (GATT) in 1991 and later became a founding member of the World Trade Organization (WTO) established in 1995 – a status it continues since the handover from Portugal to the People’s Republic of China (PRC) on 20 December 1999 by using the name “Macao, China”. This was possible because of its present constitutional status as a Special Administrative Region (SAR) of the PRC, which – in line with the “One Country, Two Systems principle”, grants it vast autonomous powers domestically as well as internationally. Today the Macao SAR, as it is officially called now, is thus truly a unique “glocal”, i.e. local and global player, which offers many more distinct features in terms of law, international trade, culture, language and the economy. These and many more features have earned it the connotation as a “global village”, the “Las Vegas of the East” or “Monte Carlo of the Orient” in view of its status as the world’s largest gaming hub, or a “micro-laboratory” for both the global creative economy as well as for research in comparative and global law. This chapter highlights some of the unique features of Macao and outlines the trade-related challenges that every separate customs territory or WTO Member faces with a view of identifying the most important lessons that can be learned from Macao’s role in the history, the present and the future.