plain sailing

American  

noun

1. Navigation. sailing on waters that are free of hazards or obstructions.

2. an easy and unobstructed way, course, or plan.

   As an heir to a large fortune, he looked forward to financial plain sailing.

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plain sailing British  

noun

1. informal smooth or easy progress

2. nautical sailing in a body of water that is unobstructed; clear sailing Compare plane sailing

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plain sailing Idioms  

1. Easy going; straightforward, unobstructed progress. For example, The first few months were difficult, but I think it's plain sailing from here on. Alluding to navigating waters free of hazards, such as rocks or other obstructions, this term was transferred to other activities in the early 1800s.

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Etymology

Origin of plain sailing

First recorded in 1800–10

Example Sentences

Trading oil at present is no plain sailing because transiting a tanker through the Strait of Hormuz is no plain sailing, either.

From MarketWatch • Apr. 9, 2026

Not all of Alcaraz's career has been plain sailing.

From BBC • Feb. 1, 2026

Yet it has not all been plain sailing.

From BBC • Nov. 6, 2025

It has not all been plain sailing, of course, since Howe's appointment or the takeover a few weeks prior.

From BBC • Oct. 5, 2025

Life is not all plain sailing over sunlit seas, for by-and-by the clouds bank up, storms come on, and the good ship has to do battle with wind and wave.

From From Squire to Squatter A Tale of the Old Land and the New by Stables, Gordon