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This book investigates the adoption of Information and Communication Technologies (ICTs) in Caribbean travel firms, particularly for sales and marketing purposes. By examining the decision-making process in tourism companies deciding whether to become more dependent on digital capabilities and artificial intelligence, this text seeks to understand the role of strategy and resources in technology adoption. Further, the author assesses the role of factors both external (such as culture) and internal (such as leadership) in this strategic process. Economies in the Caribbean are reliant on tourism to bring prosperity to the region, and with the onset of the COVID-19 pandemic, the industry is being forced to transform the way it operates. With implications for those studying organizational behavior as well as strategic and tourism management, this study analyzes rapid change in this pivotal industry.