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I have been thinking about a scenario where I have a friend who has gotten sick and wants me to fly their aircraft with their family members for compensation since I am a commercial pilot. The flight consists of being non-stop, more than 25 NM away, and returning to the same airport with the purpose of sightseeing. Would this be legal?

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Yes. If you're flying their aircraft there is no rule against you being compensated and this is a legal part 91 operation. It's no different than being hired to fly someone's business jet.

But you need to be careful here. The owner of the plane hiring you to fly his family around is fine. But the family members themselves must not be paying customers. That could essentially turn you plus the owner into an illegal charter operation.

If there are any complicating factors at all you would be wise to talk to the FSDO and/or an attorney before accepting such a job.

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