If you're looking for a good old school point-and-click adventure game, I highly recommend hunting down a copy of Torin's Passage: http://www.allowe.com/Torin/index.htm
Lowe designed the game so he could play it with his daughter - he's most famous for working on the baudy Leisure Suit Larry titles. That having been said, there's some sly humor there that only adults will understand. But at heart, it's a fun family game - there's even a hint system so little kids don't get too frustrated with it.
The Windows version never worked well even on Windows 95, but the DOS version should run perfectly in DosBox.
An adequate bootstrap is a contradiction in terms.