A measure of the degree of departure of a landscape from its range of historical conditions can provide a means for prioritizing and planning areas for restoration treatments. There are few statistics or indices that provide a quantitative context for measuring departure across landscapes. This study evaluated a set of five similarity indices commonly used in vegetation community ecology (Sorenson's Index, Chord Distance, Morisita's Index, Euclidean Distance, and Similarity Ratio) for application in estimating landscape departure (where departure = 1 - similarity). This involved comparing composition (vegetation type by area) of a set of reference landscapes to the compositions of 1,000 simulated historical landscapes. Stochastic simulation modeling was used to create a diverse set of synthetic reference and historical landscapes for departure index evaluation. Five reference landscapes were created to represent various degrees of expected departure from historical conditions. Both reference and historical landscapes were created to contain four important factors that could potentially influence departure calculation: (1) number of classes defining landscape composition, (2) dominance of the classes, (3) variability of area with the classes, and (4) temporal autocorrelation. We found that most evaluated indices are useful but not optimal for calculating departure. The Sorenson's Index appeared to perform the best with consistent and precise behavior across the ranges of the four treatments. The number of classes used to describe vegetation had the strongest influence on index performance; landscape composition defined by few classes had the least accurate, most imprecise, and most highly variable departure estimates. While results from this study show the utility of similarity indices in evaluating departure, it is also evident that a new set of statistics are needed to provide a more comprehensive analysis of departure for future applications.