Flying can be expensive and highly technical depending on where you are and what you fly
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 my regret was not taking them on any extended trips
Sailing. Flying a plane.
Sailing canoe rigs can be fun, and you might be able to find a decently cheap Sunfish or Laser and have a ton of fun.
The plane one is a bit tougher.
Gliders/sailplanes should be reasonably accessible.
Both great fun.