|Horizontal collaboration is a strategy that has increasingly been used for improving supply chain operations. In this paper, we analyze the benefits of using a collaborative approach when optimally planning the wine grape harvesting process. Particularly, we assess how labor and machinery collaborative planning impacts harvesting costs. We model cooperation among wineries as a coalitional game with transferable costs for which the characteristic function vector is computed by solving a new formulation for planning the wine grape harvesting. In order to obtain stable coalitions, we devise an optimization problem that incorporates both rationality and efficiency conditions and uses the Gini index as a fairness criterion. Focusing on an illustrative case, we develop several computational experiments that show the positive effect of collaboration in the harvesting process. Moreover, our computational results reveal that the results depend strongly on the fairness criteria used. The Gini index, for example, favors the formation of smaller coalitions compared to other fairness criteria such as entropy.