Visitors’ perceptions of traditional homestead windbreaks on the Ryukyu Archipelago were determined in this study by analyzing the user-generated comments (UGC) on Instagram. It was found that an overwhelming majority of tourists used phrases like “spiritual,” “greenery,” “nature,” and “healing” to describe their feelings while visiting the dense windbreaks, in comparison with local residents’ perceptions of “windbreak” and “firebreak” in their stories. By analyzing the Instagram UGC, useful information related to tourists’ assessments, perceptions of windbreaks, and disadvantages of trees with numerous mosquitoes, was obtained. Many tourists assessed dense tree lines as sacred and spiritual. Furthermore, many tourists preferred a comfortable tour by riding a bicycle and a micro kickboard without walking too much. This study demonstrated Instagram as an important source of tourists’ perceptions of landscape amenities, which can inform tourism management organizations (TMO). It is recommended that homestead windbreaks are promoted on the websites of TMO of isolated islands and remote areas, and as a popular destination that is part of local culture and alternative tourist attractions.