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 the 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. Andrew Spencer is Deputy Executive Director and Senior Lecturer at the Mona School of Business and Management, as well as Head of the Centre for Tourism and Hospitality Management at the University of the West Indies, Jamaica. He is the former Executive Director of the Tourism Product Development Company, the agency responsible for the maintenance, development and enhancement of the tourism product in Jamaica. He is the author of Travel and Tourism in the Caribbean, published by Palgrave Macmillan and has published extensively in international journals.