Working during travel

I'm planning out a long weekend trip by the end of the year, however I want to be able to complete some work on Friday, the day I travel, so I wouldn't have to take that day off. 

What I'm unsure about is what type of Wifi setup to purchase/use on the plane/hotel that is secure as the documents I work on are confidential. I know a lot of people here work during vacation/business trips so any advice here would be really helpful (I'm a clueless first year). Recommendations for specific airlines/hotels would help too if that matters.

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