Chestnut trees are economically exploited in temperate regions of Asian countries, Oceania and the European Iberian Peninsula. Chestnuts are sources of protein and carbohydrates and are eaten in many ways, mainly roasted during cold temperatures. Chestnuts may be suitable for cultivation in tropical regions, but to do this, the potential cultivars’ productive performances should be quantified. Thus, this study determined the performances of chestnut cultivars in a tropical region using the Taishowase, Isumo, Tamatsukuri and Okuni cultivars. The cultivars’ phenological development, including the beginning and end of flowering and harvesting, as well as each cultivar’s nut production were evaluated over four production cycles. The Taishowase and Okuni cultivars were shown to be the most promising for tropical regions because they showed greater adaptability and production stability.