Dermatobia hominis, also known as the human botfly, is native to tropical and subtropical Central and South America and seen in travelers from endemic to temperate regions including the United States and Europe. Cutaneous infestation botfly myiasis involves the development of D. hominis larvae in the skin and is common in tropical locations. The distinct appearance of a cutaneous D. hominis infestation facilitates early diagnosis and intervention where cases are common. However, the identification of D. hominis in temperate regions may prove challenging due to its rarity. D. hominis may be misdiagnosed as folliculitis, an epidermal cyst, or an embedded foreign object with secondary impetigo. One should have a heightened suspicion in someone returning from a vacation in an endemic area, such as Belize. Here we describe the presentation, differential diagnosis, and treatment and encourage enhanced preventative measures among tourists when visiting tropical and subtropical regions. Additionally, we propose a novel classification system for assessing the various stages of infestation and suggest that patients reporting travel to Latin America and experiencing pain disproportionate to an insect bite should lead physicians to consider myiasis caused by D. hominis.