There have been a few threads in the past about what people use miles for, though the ratio across all the forums is probably 50:1 for threads about earning them vs. threads about using them. I'm with a large group that uses them mostly for upgrades and gifts. The chance to earn miles for a low fare and upgrade is too good to pass up!
That said, Watchful's vacation sounds great. If any of your family members decides not to go, can I get waitlisted?