Boswell and Dr Johnson met Sandie Macleod, as he was known, at Raasay on September 8, 1773. 

According to Boswell, "Sandie MacLeod, who has at times an excessive flow of spirits, was, in his days of absconding, known by the name of MacCruslick, which it seems was the designation of a kind of wild man in the Highlands, and so he was called here. He made much jovial noise, but was too violent for my nerves, though they are now pretty well stiffened. Mr Johnson was so delighted with this scene that he said, “I know not how we shall get away.”

On September 9, in the afternoon, Boswell and MacLeod "went out with guns to try if [they] could find any black cock", but without success. They did, however, encounter a heavy rain, becoming a good deal wet. 

Boswell and Dr Johnson met Col. Macleod at Raasay on September 8, 1773. They had met his brother, Professor Roderick Macleod, in Aberdeen a few weeks earlier.

Boswell and Dr Johnson met young Mackinnon upon their arrival on Raasay on September 8, 1773. Boswell described him as "a young man of small size, delicate constitution, feebleness of voice and nearness of sight, but I was told had great knowledge, and hurt himself by too much study, particularly of infidel metaphysicians." Following a conversation with Mackinnon on September 9, Boswell told Dr Johnson, that "[Mackinnon] had studied himself into infidelity", to which Johnson replied that "he must study himself out of it again. [...] Drinking largely would sober him again."

Boswell and Dr Johnson met Dr MacLeod on Raasay after their arrival on that island on September 8, 1773. Boswell described him as a "sensible, civil man, [who] I am told has good skill." Boswell further wrote that Macleod had had bad health for some years and had given over his practice. 

In the afternoon of September 12, 1773, and back on Skye, Johnson and Boswell rode from Portree to Macleod's house at Eyre, where they had a comfortable dish of tea and met the Doctor's wife and brother. After this, the Doctor rode with them a mile further on to the house of Allan MacDonald, tacksman of Kingsburgh, and his wife, the celebrated Flora MacDonald.

Boswell and Dr Johnson were greeted by Macleod and his large family as they arrived on Raasay on September 8, 1773. The travelling companions were both exceedingly happy with their reception and the general hospitality extended to them during their stay at Raasay, and Macleod - or Raasay, as he was known and referred to - received much praise by them both in their respective accounts of their journey.

Raasay and a few of his kinsmen joined Boswell and Johnson on the boat as they departed Raasay again on September 12, sailing to Portree on Skye. There, Boswell, Raasay and some of the others visited an emigrant ship, Nestor, that was lying in the harbour. They later dined at the local inn, before parting ways "with cordial embraces [...] hoping to see them again."

MacLeod was pilot on the boat taking Boswell and Dr Johnson from Broadford on Skye to the isle of Raasay on September 8, 1773. With them was also the rev. Donald Macqueen.

Boswell described Macleod as "quite the Highland gentleman; of a stout well-made person, well-proportioned; a manly countenance browned with the weather, but a ruddiness in his cheeks, a good way up which his rough beard extended; a quick lively eye, not fierce in his look, but firm and good-humoured. He had a pair of brogues, tartan hose which came up only near his knees and left them bare, a purple camblet kilt, a black waistcoat, a short cloth green coat bound with gold cord, a yellowish bushy wig, a large blue bonnet with a gold-thread button.314 I never saw a figure that was more perfectly a representative of a Highland gentleman. I wished much to have a picture of him just as he was. I found him frank and polite, in the true sense of the word."4

As they sailed on in the boat to Raasay, Malcolm "raised an Erse song, Hatyin foam foam eri, to which he gave Jacobite words of his own", before "taking an oar and [rowing] like a hero." He also told Boswell and Johnson about his experience with the Old Pretender during the Jacobite rising in 1745, and also told them that he still had an empty bottle from which the Prince had drunk brandy, and a silver stock-buckle which had been given to him by the Prince. Boswell related how he and Malcolm "became great friends", and that Malcolm "offered to make me a present of the bottle", which Boswell refused, saying that "nobody should have it but himself".

On September 10, Malcolm joined Boswell for a walk around Raasay together with Donald Macleod of Canna, John Macqueen, and Boswell's servant Joseph.

Boswell and Dr Johnson met Macqueen on the coast of Skye near Broadford on September 8, 1773, when he arrived to accompany them on their crossing to the isle of Raasay. Boswell instantly took a liking to the old churchman, describing him as "a decent minister, an elderly man with his own black hair, courteous and rather slow of speech, but candid, sensible, and well-informed, nay, learned."

Macqueen also joined them on the trip back to Skye, arriving with them at Portree on September 12. According to Boswell, "Mr. Donald Macqueen went to church and officiated in Erse, and then came to dinner."

Boswell and Dr Johnson met Rev. MacKinnon and his wife on September 6, 1773, at the reverend's father-in-law near Broadford on Skye.

Boswell and Dr Johnson arrived at Coirechatachan on September 6, 1773, while on their tour of Scotland. They were greeted by the tacksman, Lachlan MacKinnon, who Boswell described as "a jolly big man". They were joined by several of MacKinnon's family and neighbours, and Boswell wrote of the occassion that "It was really an agreeable meeting; and we for the first time had a specimen of the joyous social manners of the inhabitants of the Highlands", and "How superior was our reception here to that at Sir Alexander’s!" 

They stayed at Coirechatachan for two days, until the weather allowed them to go on boat to their next destination, the Isle of Raasay.

Boswell and Dr Johnson first met Macdonald when they were guests of Sir Alexander Macdonald at Armadale on September 4, 1773. On the next day, Sir Alexander and Boswell went to Macdonald's, who was Sir Alexander's facto in the district of Sleat, after dinner, where they were served punch and port. Boswell, in his journal, admitted that he "drank freely of punch by way of being social, and after supper I drank freely of port by way of keeping off a taedium vitae. Altogether, I had too much."