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1.
An individual who boldly parachutes from the stratosphere down onto a surfboard in the ocean.
Bobby became a dayvan cowboy just last thursday
by battle_pope June 29, 2006
 
2.
'Dayvan' is a phonetic spelling of the the word divan, which is the name of a sofa-like piece of furniture, and seems to be commonly used in more rural settings.

'Dayvan cowboy' is just another clever way of describing someone who experiences excitement vicariously, rather than actually doing it themselves. Similar to 'armchair warrior', 'armchair quarterback', etc.
He's a real dayvan cowboy - all he does is watch tv, rather than going out and doing it himself.
by VenturaII March 13, 2011
 
3.
A person who spends their days, or, a presumably large amount of time during days, traveling on the road in a motor vehicle; in this case a 'van'.

A road tripper and/or warrior.
Musicians, Road Warriors, Nature Seekers, Dayvan Cowboys
by ACYLTEA November 30, 2008