Palynological results from opposite sides of the northernmost Antarctic Peninsula provide insight on terrestrial vegetation and sea-surface conditions immediately before the Eocene–Oligocene transition (EOT), through Early Oligocene glacial conditions and the subsequent Late Oligocene interglacial interval. A latest Eocene sample set from the uppermost La Meseta Formation on Seymour Island, James Ross (back-arc) Basin, records a low-diversity Nothofagus (southern beech)-dominated vegetation with some podocarp conifers similar to Valdivian-type forest found today in Chile and Argentina. Marine organic-walled phytoplankton include leiospheres and Eocene dinoflagellate cysts such as Vozzhennikovia rotunda, V. apertura, Senegalinium asymmetricum and Spinidinium macmurdoense. Immediately before the EOT near the top of the section the decrease in terrestrial palynomorphs, increase in reworked specimens, disappearance of key dinocysts, and overwhelming numbers of sea-ice-indicative leiospheres plus the small dinoflagellate cyst Impletosphaeridium signal the onset of glacial conditions in a subpolar climate. Early to Late Oligocene samples from the Polonez Cove and Boy Point formations on King George Island, South Shetland Islands (magmatic arc), yielded an extremely depauperate terrestrial flora, likely resulting in part from poor vegetation cover during the Polonez Glaciation but also because of destruction of vegetation due to continued regional volcanism. The prevalence of sea-ice-indicative leiospheres in the marine palynomorph component is consistent with polar to subpolar conditions during and following the Polonez Glaciation.