Social Media has changed how individuals share experiences, especially regarding their travels. Instagram is one of the most prominent social media platforms, and it is popular due to its focus on visually appealing content. This study explores how backpackers in Costa Rica share their experiences on Instagram. Ten backpacking respondents were interviewed on-site in Costa Rica to achieve this exploration. The data was analyzed using the well-established brand personality framework. The leading brand personality dimensions were excitement, sincerity, and ruggedness. While excitement and ruggedness are context-bound, sincerity is a more generic dimension. Destination managers can use these results to evaluate how they best connect their destinations to these dimensions. Congruent management can enhance travelers’ sharing and engagement with their audience on social media.