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

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

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

There we will leave him, and see what had befallen Sid; for his adventures were more exciting than Hugh's, though all seemed plain sailing when he started.

From Spinning-Wheel Stories by Alcott, Louisa May