The last decade has seen a significant interest in the relevance of social media to the field of hospitality and tourism. Social networking sites such as TripAdvisor allow the publication of user-generated content (UGC) that gives customers the chance to share their experiences and record their satisfaction. These actions represent an essential form of electronic “word-of-mouth” that can influence the decision-making process of other visitors. This article analyses tourists’ perceptions of Koločep Island on the TripAdvisor platform. All comments from 2008 to 2022 that were posted in English were analysed. The most important things for visitors revolved around the “Island” category, where they made comments about beaches and things to do and see on the island. The most devastating result was the confirmation that visitors only travelled during the main tourist season—summer. This confirms the major problem of seasonality on the Dalmatian coast and sounds the alarm for the need for immediate change.