Sailboat was recorded while Jonathan and his wife Carolina were living in Pictou County, Nova Scotia circa 1973 through 1979. Jonathan recorded the album as a draft dodger, after leaving the USA to avoid being conscripted by the American government for the war in Southeast Asia. The song Carolina, Caroline was written about his wife, seen piggybacking on the back of the album. Three of the tracks were written by fellow American draft dodger Jesse Winchester.
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