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

In the post, Greg said he wanted to share the personal update as "life isn't plain sailing but we've got to carry on".

From BBC • Mar. 9, 2026

Yet it has not all been plain sailing.

From BBC • Nov. 6, 2025

Making the switch from YouTube isn't always plain sailing, though, as shown by Mr Beast's 2024 Amazon Prime show Beast Games.

From BBC • Aug. 21, 2025

It was all plain sailing when the Doctor himself was in the chair.

From From School to Battle-field A Story of the War Days by King, Charles