This study has evaluated five years (2016–2020) of Himawari-8 (H8) Sea Surface Temperature (SST) Level 2 Pre-processed (L2P) data produced by the Australian Bureau of Meteorology (Bureau) against shipborne radiometer SST measurements obtained from the Infrared SST Autonomous Radiometer (ISAR) onboard research vessel RV Investigator. Before being used, all data sets employed in this study have gone through careful quality control, and only the most trustworthy measurements are retained. With a large matchup database (31,871 collocations in total, including 16,418 during daytime and 15,453 during night-time), it is found that the Bureau H8 SST product is of good quality, with a mean bias ± standard deviation (SD) of −0.12 °C ± 0.47 °C for the daytime and −0.04 °C ± 0.37 °C for the night-time. The performance of the H8 data under different environmental conditions, determined by the observations obtained concurrently from RV Investigator, is examined. Daytime and night-time satellite data behave slightly differently. During the daytime, a cold bias can be seen under almost all environmental conditions, including for most values of wind speed, SST, and relative humidity. On the other hand, the performance of the night-time H8 SST product is consistently more stable under most meteorological conditions with the mean bias usually close to zero.