I don't think there's a foolproof way. Maybe the motoring organisations will provide a caravan route if you're a member?
Just plan, would be my first suggestion - use a decent road atlas - we use one en route as well along with the sat nav, which we don't follow blindly! Always use the approach instructions given by the club or site.
If you're using sat nav, don't even think about using shortest route option. Pay very close attention to road signs - width limits, single track roads, roads unsuitable for caravans/large vehicles, steep hills etc.
Our caravan is no wider than the car, so the main concern for us is single track roads.
As to getting stuck and reversing, I don't think anybody wants to do that whether they're on their first few outings or not - you can't do it on your own as you are blind on one side as soon as you have any angle on, and you can't see directly behind the van anyway, so you need a competent helper to guide you - never works when we try it ;-)