Recording his daily travels in journal form, Boswell begins with an explanation of travel preparations. He has convinced his friend Samuel Johnson to accompany him on a scenic tour of Scotland from Edinburgh to Inverness and back around in a circuit. They prepare the appropriate foods, clothes, and make arrangements for lodgings. The trip lasts from August to November, 1773.
Concerned primarily with the scenic element of their travels, Boswell keeps a near daily log of his observations, with a keen eye for detail and natural beauty. He often engages in conflict with his friend, but they make complimentary traveling partners. Boswell merely prefers the sights to activity. In fact, Boswell barely escapes several conflicts with people whom he meets along the journey, even in the publishing of this journal, because of his brash and confrontational representation of their interactions. Among these is namely Sir Alexander Macdonald whom he met at Armandale. Boswell developed a fondness for Lady Macdonald which created high tensions between the two both in Boswell's relationship to Macdonald and in his account afterwards.
Together Boswell and Johnson travel first along the northeast to St. Andrews, Aberdeen, and then Inverness. These are highlands, populated closely near many Scottish islands. In the Hebrides, a mountain range along the islands, they vacation in leisure for a few weeks. Finally, they stop by Boswell's home estate in Auchinleck before returning to Edinburgh.
