Consumer dissatisfaction with the flavor quality of many modern fresh market tomato varieties has fostered breeders’ interest in sensory quality improvement, and the demand for traditional varieties, which are generally associated with better flavor. To achieve further knowledge on the factors influencing the sensory quality and consumers’ preferences and perception, European traditional and modern fresh market tomato varieties were grown and evaluated in France, Italy, and Spain. Different growing conditions were tested in France (soilless vs. soil) and in Spain (open field vs. greenhouse), while in Italy fruits were evaluated at two ripening stages. Fruit quality was assessed by integrating physicochemical analyses, sensory profiles, and consumer tests. In all three countries, overall modern varieties were perceived as having more intense “tomato flavor” and “overall flavor” than traditional ones. In France and Spain, consumers’ preferences were more oriented towards modern varieties than traditional ones. Significant growing condition effects were found on sensory and physicochemical traits, while the effect on consumers’ overall liking was not significant, largely depending on the genotype. A fair agreement between product configurations from descriptive analysis by trained assessors and Check-All-That-Apply (CATA) questions by consumers was observed. Penalty-lift analysis based on CATA allowed identifying positive and negative drivers of liking.