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

Dictionary.com Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2013.
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Collins
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
Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009
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00:10
Plain sailing is always a great word to know.
So is callithumpian. Does it mean:
a screen or mat covered with a dark material for shielding a camera lens from excess light or glare.
a children's mummer's parade, as on the Fourth of July, with prizes for the best costumes.
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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