Managing the transition from conventional agriculture to agroecology needs to account for the diversity of farming systems. Here we evaluate whether indicators based on agrodiversity and implementation of agroecological practices can discriminate types of farms with different trajectories in the context of the agroecological transition. The indicators tested were coupled with production factor, performance and strategy variables to better target their need for innovation. We propose a composite indicator that captures the main agroecological practices implemented within the study area: the French Caribbean islands of Guadeloupe and Martinique. Data was collected from 215 farms selected on the basis of their production strategy and their diversity. Eight variables related to production factors (farm size, equipment number, total and family labor), performance (total gross margin per hectare), surface devoted to implementing agroecological practices (SAEP), diversity (number of species produced), and local context integration (proportion of affiliation to professional organizations) were used to perform correlation and multivariate analyses (PCA and cluster analysis). The two PCAs (one with and one without SAEP included in the analysis) grouped agroecological practices, diversity, family labor and gross margin per hectare variables and opposed them against production-factor variables (farm size, total labor, and equipment number). Five farm clusters were identified when including the agroecological practices indicator in the analysis, i.e., 1) small diversified family farms, 2) medium-sized diversified family farms, 3) medium-sized diversified entrepreneurial farms, 4) medium-sized specialized entrepreneurial farms, and 5) large specialized entrepreneurial farms, and these clusters showed different degrees of agroecological and diversity practice implementation. Two extreme strategies of agroecological improvement were identified between large farms with high levels of production factors mainly oriented toward a light transition based on perpetuating existing agricultural models, and small family farms with high levels of diversification that already implement agroecological practices. Limits of this new composite indicator are discussed, and avenues for improvement are proposed.