Industries aim to ensure extra virgin olive oil (EVOO) stability especially during commercial activities up to use by end consumers. The objective of this work was to set up predictive models of EVOO stability during commercial activities. Stability was studied on five lots of a batch of Tuscan virgin olive oil to simulate different commercial activities. Chemical, physical, and sensory analyses were carried out on EVOO samples. Experimental data were processed by multivariate analyses to select significant parameters and by regression analyses to set up kinetic models. A few parameters were found to be significant: hydroxytyrosol and tyrosol contents, carotenoid absorbance at 475 and 448 nm, alpha-tocopherol content, Rancimat induction time, and K(232). It was also shown that the stability of this EVOO was not significantly influenced by different uncontrolled bottling, transport, and storage conditions in supermarkets. Empirical models were set up to predict the time to reach a reference value for K(232).