Second home tourism has been a primary cause of real estate development of the Spanish coasts since the 1970s. Historically, Northern Europeans have been the driving force influencing the "second home residential tourism" market in Spain, which attracts thousands of foreign customers per year. Spain’s coastal region has undergone dramatic development due to this demand and in recent has become famous for being a prime destination for international retirees who tend to have their own specific demands and requirements when looking to purchase property abroad. Taking into account that the "baby-boomer" generation is poised for retirement within the next decade, Europe and its planners will need to develop proper responses through guidelines and planning of its territory, housing, and development, particularly those along the Mediterranean Sea. As a result, this research seeks to evaluate the territorial, cultural and natural attributes that underpin the decisions of the target group in case they search for a second home. The study area selected is situated along the Costa Brava on the Mediterranean Sea in the northeastern part of Spain, meanwhile the methodology consists of a 2016 self-administered questionnaire involving 191 European tourists, of which most were over the age of 50. A set of attributes were provided and categorized into the three categories mentioned previously, with a Likert Scale related to levels of importance. At first, the result’s rank was based on the attributes´ average weighted score. The top three considerations influencing the participant’s selection were cultural offerings including friendly people, security and cultural diversity, following by two of built environment attributes of proximity to shopping and well-maintained streets and sidewalks, and the natural environment attributes. Having evaluated the participants stated choices, further statistical differences were analyzed using a Pearson Chi-Square test which highlights the degree to which the specific stated characteristics of the participants influence their choices; for instance, the presence of a mild winter is more important for this group than others, which is further supported by previous studies. The final step is the use of a logistic regression model to ascertain the effects of the territorial, natural and cultural factors on the likelihood that participants choose a second home on the Costa Brava.