DH and I paid for our best friend's honeymoon!
For context, this has been DH best friend since they were both 5, the three of us were all roommates and best friends through college, he officiated our wedding and married us, and now he found a really lovely lady to add to our best-friend group, she fits in like a charm. However, they live in a slightly depressed area and don't have the highest income, and were planning on drastically cutting their plans for their honeymoon to make things work financially.
We love these people like siblings, and they are financially smart, they just don't have a lot of resources in the first place. In contrast, DH and I make $250k per year combined and live on $45k. So DH and I just looked at each other when they mentioned that plan off-hand and we both had the same thought that we telepathically communicated to each other: we can pay for that. I whipped out my checkbook and said "$3000 should about do it", scribbled it out, and gave the slip to his shocked fiancee. They initially refused to take it, and threatened to shred it, but we insisted it was our wedding gift and promised to not get them any other gifts. These people are lovely and deserve an incredible honeymoon so we were happy to pay for it and give them a needed financial break.
Another thing we have done is give each of our younger siblings $500 after their HS graduations, and $1000 after college graduation (to help with security deposits on apartments, etc). DH's family is from a rural area and doesn't have much money to help their kids launch, and my family is not quite so desperate but also not rolling in the dough. So, we figure DH and I got incredibly lucky and can use our cushy position to help give our younger sibs a nice boost/security. There are 4 total younger siblings, all of which are still in college so we are saving up that $4k to give to them later (it's a surprise).