I'd say its down to what links the missions together. Strong stories and characters make open world games work, weak ones leave the games feeling like a bunch of checkpoints.
IMO games that I have played that do it well are GTA: San Andreas, AC2
Games I have played that IMO do it badly are GTA4, Oblivion
and of course there are many that fall in between but to say they are all boring is a very closed minded view.







