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

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

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

But while Gordon's smile was one of genuine admiration, his father's still savored of that irony which warned the younger that all was by no means plain sailing yet.

From The Son of his Father by Cullum, Ridgwell