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.

---

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

---

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.

---

Etymology

Origin of plain sailing

First recorded in 1800–10

Example Sentences

See Examples For:

plain sailing

More recently they drew with Thomas Tuchel's England in a friendly at Wembley, but it has not all been plain sailing for Uruguay under Bielsa.

From BBC ● Jun. 4, 2026

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

However, it was not all plain sailing when it became clear he was not going to reach the playing heights achieved by his father.

From BBC ● Oct. 31, 2025

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

From The Red Room by Strindberg, August