Bangladesh is one of the most disaster-prone countries worldwide. Every year, the country sees a small- or large-scale disaster, with past disaster history showing that cyclones have been a major phenomenon. Cyclone Bulbul made landfall on the southwestern coast of Bangladesh on November 10, 2019, with an average storm surge height of 1.0 to 1.5 meters—resulting in the inundation of low-lying areas in 14 coastal districts. This study conducted a questionnaire survey of 413 households in Gabura, a union under Shyamnagar Upazila of Satkhira District, from mid-February to mid-March 2020 to investigate respondents’ evacuation experience during Cyclone Bulbul. The questionnaire survey comprised both qualitative and quantitative approaches that analyzed disaster preparedness level, successful evacuation scenarios, and early evacuation decisions and their implementation in Gabura Union during Cyclone Bulbul. The survey results revealed that approximately 55% of the respondents evacuated during Cyclone Bulbul. Among them, 47% made early evacuation decisions, but an analysis of their evacuation starting time revealed that only 35.5% of them evacuated early before Cyclone Bulbul made landfall. Moreover, this research highlighted the importance of having adequate preparation time before starting evacuation, with most of the household respondents stating that they needed 2 hours in preparation time before starting evacuation. However, the preparation time varied between 1 and 6 h depending on the evacuation stage, the type of preparation activities, and the presence of vulnerable members in the house. Both categories of respondents, that is, those who made early evacuation decisions and those who followed through, cited evacuation companions, the presence of sick members in the house, distance from home to shelter, evacuation travel time, and socio-economic characteristics as common influential factors. Respondents in the emergency evacuation category identified previous disaster experience, the presence of sick members in the house, and socio-economic aspects as the factors that they considered while making evacuation decisions during Cyclone Bulbul. This analysis of factors influencing early evacuation decisions, early evacuation, and emergency evacuation helped shed light on people’s perceptions about disasters, which can guide authorities in taking policy actions to improve early evacuation possibility and issuing early evacuation orders to ensure safe and successful evacuation during cyclones or other disasters in the future.