Background: An efficient first-aid system usually supports ground services with a helicopter emergency medical service (HEMS). An HEMS is important for patients with acute chest pain on remote islands. The current study sought to identify the characteristics of HEMS in acute chest pain cases on the Croatian Adriatic islands over a four-year period. Methods: We conducted a four-year observational study to investigate HEMS from Adriatic islands. The study population consisted of all patients with acute coronary syndrome or pulmonary embolisms who were urgently transferred by HEMS to the University Hospital in Split 1 June 2018–1 June 2022. Results: During the observation period, 222 adult patients (67 females, or 30.2%) were urgently transferred. The mean age was 71.81 ± 13.42 years. The most common diagnosis was ST-elevated myocardial infarction (113, 50.9%). Most of the HEMS cases were from Hvar (91, 41.0%). The mean call-to-flight time was 19.10 ± 10.94 min, and the total time from call to hospital was 68.50 ± 22.29 min. The total time from call to hospital was significantly correlated with call-to-flight time (r = 0.761, P < 0.001). Of the 222 participants, 5 (2.25%) were transported for more than 120 min, and 35 (15.8%) were transported for more than 90 min. Conclusion: This study provided a detailed insight into HEMS in the area of the Croatian Adriatic islands. The average time from the call to the helicopter taking off was 19.10 min. An increase in dispatching time has a significant impact on the prolongation of the total time for the hospital admission. Shortening the response time is critical to reducing hospital arrival time.