I've not ridden with a kid myself but in my travels I've talked about it with locals in places out is common. My thoughts:
Do you ride with him regularly now? To the store? To the park? For a fun day ride? If that works try an overnight then go for it. If you are not already riding with him I would really question the wisdom of going right into a long trip!
I've seen kids riding pillion too often in Latin America to believe it cannot be done safely. However, those kids literally grew up being a passenger their whole lives, starting strapped to mom's back.
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