Despite being a regular in the south of France during his summer holidays, Ferguson has decided to sail from Oban to Iona.
Ferguson is joined by his wife Cathy and their family, including twin sons Darren and Jason, elder son Mark and their 11 grandchildren.
Ferguson's close friend pal Craig Brown - the former Scotland manager - told the Manchester Evening News: "Sir Alex is looking forward to his family holiday of a lifetime.
"He has been in New York and France since he retired as the boss at United but his dream trip is a cruise.
"He told me himself that his family holiday of a lifetime is to go on a Scottish cruise. I thought he wanted to sail round the Caribbean or somewhere exotic.
"Sir Alex told me he was desperate to go on a cruise around Scotland. He is taking his whole family – sons and grandchildren included.
"I think the cruise starts in Oban and he will then be sailing on to Iona and he will also be taking in North and South Uist and Benbecula on the route. Sir Alex is deadly serious about this."