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

But it has not all been plain sailing for Hodgkinson since she won the Olympic 800m title at Paris 2024.

From BBC • Feb. 20, 2026

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

However, it was not plain sailing for Slot and his side as they met the eventual winners PSG in the opening knockout game.

From BBC • Aug. 28, 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

If she won—if she won!—there would be plain sailing in the domestic waters of the Morses’ life—and that had come to mean a great deal to the girl.

From The Girls of Central High on the Stage The Play That Took The Prize by Morrison, Gertrude W.