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

Hans' journey was not plain sailing and almost came to an end in the infamously steep Berriedale Braes in Caithness.

From BBC • Mar. 10, 2026

Yet it has not all been plain sailing.

From BBC • Nov. 6, 2025

However, it was not all plain sailing when it became clear he was not going to reach the playing heights achieved by his father.

From BBC • Oct. 31, 2025

I don't think it's going to be a plain sailing future.

From BBC • May 9, 2025

All is now plain sailing until you arrive at the incident of the newspaper.

From Magic In which are given clear and concise explanations of all the well-known illusions as well as many new ones. by Stanton, Ellis