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

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

From BBC • Feb. 1, 2026

It was never going to be plain sailing.

From BBC • Nov. 25, 2025

Yet it has not all been plain sailing.

From BBC • Nov. 6, 2025

You won't be surprised to hear that his engagement was not all plain sailing.

From The Red Room by Strindberg, August