This study analyzed shipboard air-sea measurements acquired by the icebreaker Aurora Australis during its off-winter operation in December 2010 to May 2012. Mean conditions over 7 months (October–April) were compiled from a total of 22 ship tracks. The icebreaker traversed the water between Hobart, Tasmania, and the Antarctic continent, providing valuable in situ insight into two dynamically important, yet poorly sampled, regimes: the sub-Antarctic Southern Ocean and the Antarctic marginal ice zone (MIZ) in the Indian Ocean sector. The transition from the open water to the ice-covered surface creates sharp changes in albedo, surface roughness, and air temperature, leading to consequential effects on air-sea variables and fluxes. Major effort was made to estimate the air-sea fluxes in the MIZ using the bulk flux algorithms that are tuned specifically for the sea-ice effects, while computing the fluxes over the sub-Antarctic section using the COARE3.0 algorithm. The study evidenced strong sea-ice modulations on winds, with the southerly airflow showing deceleration (convergence) in the MIZ and acceleration (divergence) when moving away from the MIZ. Marked seasonal variations in heat exchanges between the atmosphere and the ice margin were noted. The monotonic increase in turbulent latent and sensible heat fluxes after summer turned the MIZ quickly into a heat loss regime, while at the same time the sub-Antarctic surface water continued to receive heat from the atmosphere. The drastic increase in turbulent heat loss in the MIZ contrasted sharply to the nonsignificant and seasonally invariant turbulent heat loss over the sub-Antarctic open water.