This paper offers the perspective of a faculty member who recently started their own study abroad course. A wide range of issues are discussed, beginning with how to propose a course, and continuing to discuss course planning, creating an itinerary, managing budgetary matters and logistics, recruiting and selecting students, how to create effective course policies and how to elicit support from one’s department and college/university administration. Issues “on the ground” are also considered, including (but not limited to) emergencies and various contingency related matters. The course the presenter has led takes place during the summer in Italy, with stays in a number of cities, includes visits to over 60 sites and museums, and lasts nearly a month in duration. Though the course is taught through the Classics department, it carries cross-lists in a number of other departments—another issue that is discussed. The paper also considers the types of assignments, presentations and other coursework one can assign, as well as the specific texts and primary sources that are assigned during the presenter’s course, and why those specific items were selected for the course. The paper concludes with a summary of the challenges faced by faculty considering and offering a course for the first time, but also the tremendous rewards that a successful course will offer students, the faculty member, department and their college/university.