With the increasing globalization of the hospitality industry, expatriate assignments have become a necessary undertaken. There is a competitive advantage to be gained through expatriate managers who can operate firms effectively. Most international hotel corporations still employ expatriates to help in professionalizing the hospitality services and management in the Caribbean. However, while studies have been conducted on expatriates management in various countries, research on expatriate management in a Caribbean context have been practically non-existent, with only one study attempting to look at the area. The intent of the present exploratory study therefore is to understand expatriate general managers’ perceptions of hotel management on the island of Jamaica. Face to face interviews were conducted with 9 expatriate general managers from four and five star hotels in Jamaica between May and June 2010. Preliminary results indicate that there are a myriad of human resources, organizational and operational factors that impact hotel management for expatriates. Factors such as flexibility, cultural appreciation, patience, fairness, respect and being funny were seen as important for expatriate success in Jamaica. Managers must therefore be aware of how these issues may impact on their ability to manage effectively and be successful in their international assignments.