The extent to which toddlers have opportunities to learn in interactive, observational, and independent contexts is thought to vary by culture. However quantitative assessments of cultural variability and of the factors driving intra- and inter-cultural differences in toddler’s time allocation are lacking. This paper provides a comparative and quantitative examination of how toddlers spend their time and with whom (adults or children) in two communities (rural Yucatec Maya, urban United States). Additionally, it considers individual factors that predict time allocation. Results demonstrated that Maya toddlers spent more time in independent contexts compared to US toddlers and spent more time exclusively with other children than did US toddlers. Maya toddlers were more likely than US toddlers to spend time observing other people, however, when given the opportunity to observe others there were no differences in visual attentional allocation across cultures. For Maya toddlers maternal schooling related negatively to both time spent with other children and time spent in interactive contexts. The findings highlight the need for researchers to include diverse populations when considering early social experiences as well as assessing factors that may contribute differentially to variations in early experience across cultures.