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plain sailing

Navigation. sailing on waters that are free of hazards or obstructions.
Compare plane sailing.
an easy and unobstructed way, course, or plan:
As an heir to a large fortune, he looked forward to financial plain sailing.
Origin of plain sailing
First recorded in 1800-10 Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2018.
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British Dictionary definitions for plain sailing

plain sailing

(informal) smooth or easy progress
(nautical) sailing in a body of water that is unobstructed; clear sailing Compare plane sailing
Collins English Dictionary - Complete & Unabridged 2012 Digital Edition
© William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009, 2012
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Idioms and Phrases with plain sailing

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® Idioms Dictionary
Copyright © 2002, 2001, 1995 by Houghton Mifflin Company. Published by Houghton Mifflin Company.
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