The US President’s Emergency Plan for AIDS Relief (PEPFAR) has shifted from an emergency response to a sustainable, country-owned response. The process of transition to country ownership is already underway in the Eastern Caribbean; the Office of the US Global AIDS Coordinator (OGAC) has advised the region that PEPFAR funding is being redirected away from the Eastern Caribbean toward Caribbean countries with high disease burden to strengthen services for key populations. This article seeks to highlight and apply lessons learned from other donor transitions to support a successful transition of HIV programs in the Eastern Caribbean. Based on a rapid review of both peer-reviewed and gray literature on donor transitions to country ownership in family planning, HIV, and other areas, we identified 48 resources that addressed key steps in the transition process and determinants of readiness for transition. Analysis of the existing literature revealed 6 steps that could help ensure successful transition, including developing a clear roadmap articulated through high-level diplomacy; investing in extensive stakeholder engagement; and supporting monitoring and evaluation during and after the transition to adjust course as needed. Nine specific areas to assess a country’s readiness for transition include: leadership and management capacity, political and economic factors, the policy environment, identification of alternative funding sources, integration of HIV programs into the wider health system, the institutionalization of processes, the strength of procurement and supply chain management, identification of staffing and training needs, and engagement of civil society and the private sector. In the Caribbean, key areas requiring strengthening to ensure countries in the region can maintain the gains made under PEPFAR include further engaging civil society and the private sector, building the capacity of NGOs to take on essential program functions, and maintaining donor support for targeted capacity building and long-term monitoring and evaluation efforts.