This case report highlights the importance of a detailed travel history and the need to revisit the differential diagnosis when there is an unexpected clinical course. A previously healthy 15-year-old male presented to a hospital in Florida with a fever, cough, and shortness of breath. He was seen multiple times at urgent care centers and treated with steroids and antibiotics for community-acquired pneumonia (CAP). The patient’s chest X-rays and CT showed necrotizing pneumonia with pleural effusion, which required a chest tube. Despite broadening coverage for possible resistant organisms, his fevers and hypoxia continued. On day 14 of hospitalization, a bronchoscopy was performed, which led to the diagnosis of blastomycosis. History was revisited, and a specific travel history was obtained. The patient had been camping with his father on the Minnesota/Canada border a few months prior to his presentation.Blastomycosis is caused by a dimorphic fungus endemic in certain parts of the United States including areas surrounding the Mississippi and Ohio River valleys, some southeastern states, and areas bordering the Great Lakes. Autochthonous blastomycosis is not seen in Florida. The infection is acquired by inhalation of the organism and is associated with outdoor occupation and recreation. As with other infections with specific endemic distribution, the diagnosis of blastomycosis can be delayed if the epidemiologic link is not established. Questions about travel history need to be very specific as this could be critical in establishing the appropriate differential diagnosis and leading the workup. The patient’s lack of improvement despite appropriate antibiotic therapy for CAP led to questioning the working diagnosis, revisiting the history, and expanding the workup, which was critical in this case.