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

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Example Sentences

See Examples For:

plain sailing

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

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

Not all of Alcaraz's career has been plain sailing.

From BBC ● Feb. 1, 2026

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

All would have been plain sailing, and he could have asked Leonie with a clear conscience to share his new-found honors and wealth.

From The Duke Decides by Headon Hill

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