Vina Concha y Toro, a successful international winery based in Santiago, Chile and ranked second worldwide by Power Brand 2011, has vineyards, production, sales, acquisition and distribution in 135 countries worldwide. The company, founded in 1883, is known as a leader in Chilean wine making and produces a wide-ranging brand portfolio with its varietal categories priced from US $4.99 all the way up to its ultra premium wine priced at US $40 per bottle. This paper looks at a variety of research theories of firm internationalization dating from 1966 up to 2009, and explains and parallels those theories in terms of the firm’s successes and challenges. The paper concludes with a reflection of the company’s current international leadership position and provides insights into the winery’s future.