In the era of urbanization, small towns confront challenges in sustaining and preserving their essence and population. Historical towns have discovered their potential in tourism development, yet this opportunity often escalates into overtourism, particularly in renowned cruising destinations. This paper focuses on examples of coastal historical towns dependent on tourism revenue and faced with an excessive influx of tourists in the Mediterranean Region. The objective is to examine various cases across diverse geographical, cultural, and policy contexts to evaluate their success in achieving a balance between economic development and genius loci. This analysis seeks to identify the factors that contributed to the attainment of this equilibrium. Therefore, we selected case studies throughout the Mediterranean coast—from Saint Paul de Vence and Èze at the Azure Coast, Dubrovnik and Kotor in the Adriatic Sea, to Nafplio and Monemvasia in the Aegean Sea. The selected examples range from towns that are almost entirely depopulated to those that are suffocating from the influx of tourists. Observations on the spot and review of policies led us to the conclusion that the geography of the area and cultural values represent comparative (dis)advantages that can be influenced and shaped by policies from the time of the pre-tourist phase to the phase of overtourism. Even though the success of an early policy and the effects of investments aligned with it might be uncertain, pre-tourist policies turn out to be the most successful when it comes to balanced tourist-resident development. Determination of authorities to not only see economic benefit but also genius loci and quality of life of residents is crucial, too.