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

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

The album may have taken less than two weeks to record, but you get the impression from other interviews that the process wasn't entirely plain sailing.

From BBC • Jan. 6, 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

It will be all plain sailing now for some hours to come.

From Born to Wander A Boy's Book of Nomadic Adventures by Stables, Gordon