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Sail close to the wind

Idiomatic Phrase
Pronunciation

Understanding ARPABET Pronunciation

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The pronunciation guide uses the ARPABET phonetic system—the same system used in speech recognition and text-to-speech applications.

Vowel Examples:
AE1 = cat, bat
EH1 = bed, head
IY1 = see, me
OW1 = go, boat
UW1 = boot, do
Stress Numbers:
0 = no stress (unstressed)
1 = primary stress (loud)
2 = secondary stress (medium)
Example:
AH0 TH IY1 N AH0
= a-THEE-na (Athena)

The stressed syllable (marked with 1) is pronounced louder and clearer than others.

Quick Definition

To take risks approaching illegality or disaster; nautical metaphor describing sailing dangerously close to wind direction, risking capsizing while maximizing speed or advantage.

Detailed Definition
Sail close to the wind means to take risks, behave near the edge of acceptability, or operate just within the limits of safety, law, or propriety. The nautical image suggests skill as well as danger, since sailing near the wind requires judgement. In poetry, it can describe flirtation, satire, political dissent, moral compromise, or artistic daring. A poet may use it admiringly for boldness, or critically when clever risk-taking becomes recklessness. It suits threshold moments where control is uncertain.
Example
Example in poetry:
A sea poem might show the smuggler sailing close to the wind beneath customs lights; In satire, a clever speaker sails close to the wind with jokes that nearly become treason; The phrase means to take a risky course near the edge of what is allowed; A poet can use it for danger and daring.
Additional Notes
Sail close to the wind means act near the limit of safety, legality, or propriety, from sailing as near as possible to the wind without losing control. In poetry, it is useful for risk, temptation, social daring, political speech, or moral ambiguity. The nautical image gives danger elegance and skill. Students should ask whether the speaker is brave, reckless, clever, or self-deceived. It pairs well with sails, ropes, reefs, and narrow margins.
Also Known As
risky
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