This paper analyzes the resilience cycle in San Juan Bautista (SJB), a town in Robinson Crusoe Island which has been severely affected by four tsunamis since it was first occupied in 1591. Technical reports, press archives and zoning plans are classified according to the stages of preparation, response, recovery and adaptation, and then used to explain the factors that delay the resilience cycle following the 2010 Chile tsunami. We conclude that before this event, SJB was not prepared due to the location of critical infrastructure in the flooding zone and the lack of risk principles in land use planning. Additionally, the failure of the Chilean tsunami warning system resulted in 16 casualties. As for recovery, nearly a decade after the tsunami, SJB is the only town countrywide that has not reached pre-tsunami performance levels. The relocation of housing in highlands and the use of emergency infrastructure to guarantee continuity of basic services are partial outcomes of the process. Adaptation has shown little advance since recovery is still ongoing. The analysis suggests that a contextualized urban planning policy, taking advantage of the local conditions, expertise and building materials, as well as the involvement of the community and local government, should be adopted in island territories exposed to tsunamis.