plain sailing /ˌpleɪn ˈseɪlɪŋ/noun 2plain-sailing adjective 1 noun2 •The navigation of waters free from hazards or unfavourable winds. •(figurative) Something that is easy, simple, or straightforward; something that offers no difficulties or trouble.[H]e should give himself fair play, by trying his hand vvith the rudiments, vvhich vvould no sooner be run over, than the rest vvould become plain sailing: […] — 1796 plain-sailing adjective1 •Easy, simple, straightforward.[…] I took an uncommon fancy to him. He's a straightforward, plain-sailing fellow. I shall be very glad to see him again. — 1873