The importance of tourism in Cuba is clear given the expected 3.8 million visitors in 2018. Under the Barack Obama administration these rules were relaxed, permitting “self-certifying” travel to Cuba, meaning it was not necessary to be part of a regimented, organized group. As a result, Cuba saw the potential for a significant increase in U.S. tourists to the island. This chapter conducts a qualitative case study to examine market entry strategies, challenges, opportunities, and organizational actions of eighteen tourism businesses operating in Cuba. By illustrating how successful tourism industry companies entered the Cuban market and achieved sustainability, potential investors can learn from these experiences to build and/or fine-tune their own market-entry strategy. This study may narrow the gap between Cuba as a potential location for foreign direct investment and the specific actions taken by companies to establish business operations in Cuba.