What’s best way to do this on Mac?
This method can result in corruption of the disk image if you’re not careful.
Edit: This is probably the most seamless way to handle encryption. It’s built in to the OS and you can save the password in Keychain if you like. Used it with Dropbox for years. Just make sure to unmount and let it sync before opening the disk on another system.
Have you ever tried to restore from one such archive?
(And as someone said, duplicity).