My dad used to travel a lot for work.
He racked up thousands and thousands of frequent flyer miles on work trips. Despite them being work trips, he was able to add the miles to his personal account. He also was conscious about choosing credit card bonuses that would let him stay at hotels for free.
Eventually, he took all of us (multiple kids and a wife) to Hawaii. He spent his miles on flying all of us out, and also used a separate credit card bonus on hotel credit.
With the biggest expenses covered (housing and transportation), at the end of a weeklong vacation in one of the most expensive places in America, he spent a grand total of $1000.
That included feeding enough kids to fill a minivan, going on cool outings around Oahu, and restaurants. In fact, restaurants were probably the bulk of that expense.
I’m so glad he told us how he did this, even while I was so young. It was a passive lesson in learning that really nice things don’t have to cost you a lot if you’re both patient and clever.