Similar to the osteological study of prehistoric human remains, the study of human dental wear has been proven to afford a wealth of information on human cultural practices. This study is aimed at recording and understanding the dental wear patterns in human dentitions from the Caribbean archaeological sites of Anse la Gourde, located on the most eastern point of Guadeloupe, and Tutu located on the small island of St. Thomas, U.S. Virgin Islands. The premise of this research is the assumption that dental wear patterns are informative of a great many aspects of human health and lifestyle. The use of the mouth and teeth in both masticatory and non-masticatory activities is assumed to leave traces which can be studied post-mortem to infer the lifestyle linked to such activities. In order to build a complete picture of these activities and the lifestyle linked to the dental wear patterns, other lines of evidence are also followed here, such as ethnohistoric and ethnographical accounts, and evidence from modern dentistry. Using this combination of different lines of evidence, it has been possible to characterize the diet and a range of cultural practices of the inhabitants at each site. The individuals selected in this sample very actively engaged their teeth in many non-masticatory, culturally defined activities, which put their dentitions under a great deal of stress. It seems these people's use of their mouths and teeth in this way was a very conscious decision, characterized by their cultural background.