High humidity is a major constraint to increased tomato fruit production in a cool tropical monsoon climate. However, the genetic variation observed in Solanum pimpinellifolium makes it a good gene donor for breeding tomato cultivars capable of thriving under high humidity. The objective of this study was to estimate heterosis, heritability for higher yield, and to assess the adaptability of the genotypes to humid conditions. Genotypes were raised from five morphologically divergent parents, viz., wild parent (W)–“LA2093,” “CLN2498D” (D), “CLN2417H” (H), “Tima” (T), and “UC Dan INDIA” (U). The F1s were generated by biparental mating design using “LA2093” as a common pollen donor that was selfed to produce F2s and backcrossed to both parents to obtain BC1s and BC2s. The trial was laid out in a randomized complete block design with three replicates. Data were collected on selected yield-influencing traits and analyzed. “D × W” and “U × W” hybrids showed significant positive better parent heterosis for fruit weight per plant (30.4% and 35.5%) and total fruit yield (48.6% and 26.9%), respectively. The additive variance was higher than dominance variance for all the traits, including total fruit yield in all hybrids viz., “H × W,” “D × W,” “T × W,” and “U × W.” High narrow sense heritability estimate of ≥60% was observed in “D × W” and “U × W” hybrids for the majority of the floral and fruit traits including total fruit yield. This makes the improvement of “D × W” and “U × W” hybrids by direct selection advantageous. Hence, the adoption of selection for the affected traits in subsequent tomato breeding programs would enhance fruit yield and adaptability to humid environments.