Flying can be expensive and highly technical depending on where you are and what you fly. I had a blast while flying, got some good trips in, was able to give most of my family the experience. I gave it up when I had kids because of the priority change
I suppose sailing too depending. I did some sailing out of Boston harbor and had a blast but they were bigger boats, more expensive. Actually the place I rented from organized extended trips down the coast and my regret was not taking any
Sailing. Flying a plane.
Both great fun.
Sailing canoe rigs can be fun, and you might be able to find a decently cheap Sunfish or Laser and have loads of fun.
The plane one is a bit tougher.