Does the phrase "hitting the skies" use commonly on casual occasions?
No, the phrase "hitting the skies" is not a common phrase. To "hit" in this case refers to going somewhere quickly, and this is used commonly in the phrase "hit the road", which means to leave somewhere and travel by car. So "hit the skies" is used in a similar way here, however, it is not common to use like "hit the road".
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