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If a trip meant "for business" that results in a trip "for pleasure" can be characterized as a boondoggle, then is there a word for the converse, where a trip "for pleasure" (eg. vacation) results in seeking out and taking advantage of a business opportunity?

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    Boondoggle, according to M-W, is "an expensive and wasteful project usually paid for with public money" – NVZ Aug 24 '16 at 15:01
  • @NVZ While boondoggle can describe a range of wasteful project, it is often applied to trips masquerading as work. And the OP says the term can be characterized ..., but does not suggest that the term is limited to that example. – bib Aug 24 '16 at 15:19
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    The use of boondoggle in this question is often called a junket. – Christopher Schultz Aug 24 '16 at 19:05

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It's often called a busman's holiday

A vacation during which one engages in activity that is similar to one's usual work.

American Heritage

Collins suggests the term derives from the idea of a bus driver taking a driving holiday

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  • "Suggests" might actually be Stating The Bleedin' Obvious, I think! – Andrew Leach Aug 24 '16 at 15:05
  • However, whether one would actually seek out and take advantage and have a busman's holiday is more debatable. Isn't it usually undesirable? – Andrew Leach Aug 24 '16 at 15:06
  • @AndrewLeach And if I spend my vacation clearing the dishes, I am taking a busboy's holiday? – bib Aug 24 '16 at 15:07
  • @AndrewLeach When I (a lawyer) kept checking out local courthouses during a trip to the Caribbean, my ex-wife thought it was highly undesirable. – bib Aug 24 '16 at 15:10
  • OED traces the term back to 1893, and Wikipedia cites Erik Eckermans's World History of the Automobile in dating the advent of buses powered by internal combustion two years after that, so don't rule out horses in imaging "driver" and "driving" in the above answer. – Brian Donovan Aug 24 '16 at 16:29
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    In some cases one can combine a mostly pleasure trip to a pleasanter clime with a bit of duly paid professional work for a client who happens to be there at the time. Is that a busman's holiday? – Brian Donovan Aug 24 '16 at 16:36
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It's a rather boring and obvious answer, but what I've heard it called is working vacation (USA) or working holiday (UK)

a trip, sometimes to another country, on which you work

There is also the slang workation.

A workation is similar to a vacation where you can take your work along with you.

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Depending on your job and tax bracket, a pleasure trip where you squeeze in some business might be a tax write-off vacation.

[T]he IRS says that you can deduct expenses for taking a business trip. There is no reason the trip shouldn’t coincide with your next vacation. (Bill Walston, real estate blog)

A fellow . . . needed insurance. Problem was, he was in Branson, Mo., and wouldn’t be back to Iowa before summer. “No problem,” I told him. “Mary and I have been champing at the bit to go to Branson. We’ll meet you there." . . . Done! A tax-write-off vacation. (Curt Swarm, Newton Daily News, "My tax write-off vacation to Branson")

The line here is a bit blurry (though maybe not to the IRS), so this term might also apply to the original situation described (a pleasure trip only masquerading as business).

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