plain sailing

noun
1.
Navigation. sailing on waters that are free of hazards or obstructions. Compare plane sailing.
2.
an easy and unobstructed way, course, or plan: As an heir to a large fortune, he looked forward to financial plain sailing.

Origin:
1800–10

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Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
plain sailing
 
n
1.  informal smooth or easy progress
2.  nautical Compare plane sailing sailing in a body of water that is unobstructed; clear sailing

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
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American Heritage
Idioms & Phrases

plain sailing

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.

The American Heritage® Dictionary of Idioms by Christine Ammer.
Copyright © 1997. Published by Houghton Mifflin.
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Example sentences
Not that it was plain sailing by any manner of means.
But it will not all be plain sailing for the school.
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