We present here a comprehensive record of Miocene terrestrial ecosystems from exposures of the Monterey Formation along the Naples coastal bluffs, west of Santa Barbara, California. Constrained by an updated chronology, pollen analyses of 28 samples deposited between 18 and 6 Ma reflect the demise of mesophytic taxa that grew in a warm, wet environment during the late early and early middle Miocene and the development of a summer-dry/winter-wet Mediterranean climate during the late Miocene. Broadleaf tree pollen from mesophytic woodlands and forests now found in the southeastern United States and China (Liquidambar, Tilia, Ulmus, Carya) characterized the Miocene climatic optimum (16.9–14.7 Ma), the middle Miocene climate transition (14.7–13.8 Ma), and the interval up to ca. 13.0 Ma. Subsequently, during the late middle to early late Miocene, between 13.3 and 9.0 Ma, oak woodlands and herbs (Asteraceae, Amaranthaceae, Poaceae) from beach scrub and chaparral increased as ocean temperatures cooled and the climate became drier. Between ca. 8.9 and 7.6 Ma, pine increased mostly at the expense of oak (Quercus) and herbs, suggesting a period of increasing precipitation. During the latest Miocene (7.5–6.0 Ma), an increase of herb-dominated ecosystems (chaparral, coastal scrub) at the expense of pine reflects the full development of a summer-dry/winter-wet climate in coastal southern California.