This is a tender song of disappointment in a relationship. The song is from the album "Thunder on the Tundra" recorded in 1987 . . . "the year everything happened," according to Wilfred N. This was one of the more successful songs for Wilfred N & the Grown Men in terms of radio airplay, with plays across Canada and several stations in Europe. A version of "Sailing on a Cruiser" was recorded in live performance with the Edmonton Symphony Orchestra as part of "The Alberta Suite" performed at the Jubilee Auditorium in Edmonton, Canada.