My experience has been that the easiest method is to to upgrade one minor release at once (e.g. in your case I'd do 1.11 -> 2.0 -> 2.1 -> 2.2 -> 3.0). This has almost always gone quite smoothly, but it is somewhat tedious.

That said, jumping a bunch of releases (e.g. 1.11 -> 3.0) actually often works out just fine, especially if I've got good test coverage. It's just that when it doesn't work, it can be tricky to find out what's going wrong. That's because the release notes are typically written with just a single step in mind, so with a bunch of releases I find myself scrambling to figure out which set of notes I need to read.