In summer of 2014 I led nine students to the Lake District for a ten-day program on British Romantic literature, with a particular focus on long-time Grasmere residents William and Dorothy Wordsworth and Thomas De Quincey. I called the course “Walking with Wordsworth,” and the goal was both to introduce students to the places that inspired particular poetic and prose works of the Romantic period and to encourage students to question whether and how the geographical context matters to the reader’s interpretation of the texts themselves. Planning for the course began a year prior to departure and, per university regulations, required working closely with the coordinator of the study-abroad office at the University of Texas at El Paso (UTEP), who strongly advised using a third-party provider based in Texas with whom UTEP has successfully partnered in the past. This article describes the classroom work prior to arriving in the UK, the lodging, travel, and instructional components of the trip itself, and the benefits of using a commercial provider in planning and managing the logistics of the program. The article concludes that while using a commercial provider adds a necessary bureaucratic layer to the instructor’s planning and comes at some additional cost to the students, its professional resources can offer significant time savings and peace of mind to faculty, especially those planning a study abroad for the first time.