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

See Examples For:

plain sailing

But as Cohen points out, it is not all plain sailing.

From BBC ● Jun. 10, 2026

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

It was never going to be plain sailing.

From BBC ● Nov. 25, 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

It was a good plan, little woman; and it would have been plain sailing if only we had remembered that the girl was Hargreave's daughter.

From The Million Dollar Mystery Novelized from the Scenario of F. Lonergan by Harold MacGrath