Puerto Rico has played a pivotal role in the building of cultural chronology for the insular Caribbean, and yet little systematic work has been conducted in recent decades to assess the validity of the system(s) produced. To resolve this issue, we assembled a radiocarbon inventory comprised of more than a thousand assays, drawn from both published sources and grey literature, which was used to assess and revise (as necessary) the received cultural chronology of Puerto Rico. The application of chronological hygiene protocols and Bayesian modeling of the dates yields an initial arrival of humans to the island more than a millennium earlier than previously established, making Puerto Rico the earliest inhabited island of the Antilles, following Trinidad. The chronology of the different cultural manifestations that have been identified for the island, as grouped by Rousean styles, also is updated, and in some cases heavily modified, as a result of this process. While admittedly limited by several mitigating factors, the image that emerges from this chronological revision suggests a much more complex, dynamic, and plural cultural scenario than has been traditionally assumed, as a result of the myriad of interactions that took place between the different peoples that coexisted in the island through time.