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."1

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.

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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."

Boswell and Dr Johnson met Macleod at Armadale, where they were hosted by Sir Alexander Macdonald, on September 2, 1773. Boswell, in his journal, initially described him as "a very genteel man", but deleted the compliment shortly after writing it. On September 6, MacLeod set out with them acting as their guide on their continuing journey north towards the Isle of Raasay. 

On September 10, Boswell went out to explore the island of Raasay in the company of Macleod (Canna), John Macqueen, Malcolm MacLeod, and Boswell's servant Joseph. 

Boswell and Dr Johnson met Rorie, as he was known, his wife and his son Donald at dinner on September 2, 1773, during their visit to Sir Alexander Macdonald in Armadale. Boswell described him as "an old brisk Highlander of 68, a near relation of Alexander's". Two days later, Rorie and his wife dined with them again, and Boswell wrote in his journal that "Rorie was to be dispossessed of his farm in Glenelg at Whitsunday, and was trying to get one from Sir Alexander." They were later joined by his sons James, who was Sir Alexanders factor for Sleat, and Donald, a Lieutenant in the Grenadiers.

On September 5th, Boswell walked with Sir Alexander and Rorie to the parish church of Sleat, where they saw the monument to Sir Alexander's older brother James (d. 1766). After dinner they went to the house of Rorie's son James, where they were joined by his other son Douglas and daugher Katie. In his journal, Boswell acknowledged 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."

When Boswell and Dr Johnson were guests at Sir Alexander Macdonald at Armadale on Skye on September 2, 1773, they were joined at dinner by "a little Aberdeenshire man, a naturalist, with his son, a dwarf with crooked legs. Jeans said that he had been at Mr Johnson's in London with Ferguson the astronomer. Mr Johnson thought it strange how he found somebody in such distant places who knew him; that he should have thought he might hide himself in Skye."1

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Boswell and Dr Johnson were met by Sir Alexander and his wife at Armadale on September 2, 1773, as they arrived by boat from Glenelg on their tour of Scotland. The Lord and his Lady had come there on their way from their seat at Mugstot (Monkstadt) on the north part of Skye, to Edinburgh, and therefore had to host Boswell and Johnson at a tenant's house for the ensuing days. Their visit and Boswell's relationship with Sir Alexander were not without friction, and some of Boswell's remarks in his Journal of a Tour to the Hebrides, published twelve years later, resulted in further conflict between the two. For further about the visit to Armadale, see the To the Hebrides edition of Journal of a Tour to the Hebrides, September 2-6, 1773.

Boswell and Macdonald were 13th cousins, sharing a common ancestor in Robert Stewart, 1st Lord Lorne (1382-1449).