The purpose of this qualitative study was to explore teachers' and counselors' perceptions of the challenges of implementing service learning with fidelity to best practices consistently in a school district in the U.S. Virgin Islands and to identify resources necessary to support the implementation of best practices in service learning. With only 21% of high school graduates in the Virgin Islands advancing to higher education, understanding and addressing challenges in implementing service-learning is important for enhancing student outcomes. The study, guided by Dewey's theory of experiential education and Kolb's theory of service learning, used semistructured interviews to gather data from 10 teachers and counselors. The 178 codes that emerged from the interviews were organized into nine themes. The challenges identified by participants included aligning activities with curricular objectives, engaging students throughout the process, maintaining fidelity to best practices, establishing and maintaining meaningful community partnerships, and a lack of awareness about service learning. Resources needed to support implementation include service-learning training and professional development, sustained efforts, transportation assistance, and collaboration among teachers, counselors, and community partners. A comprehensive 3-day professional development plan was developed to address the challenges and support the successful and consistent implementation of service-learning in the school district. The findings have implications for educators, administrators, and policymakers in the U.S. Virgin Islands and beyond as they strive to enhance students learning outcomes through experiential and service-based educational approaches. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]