Matt, both the aerial tours and the visits by car (or sometimes train) have always worked well.
For these trips normally three of us travel together and we each have defined duties to make it all work (i.e. one sorts accommodation, another transport and so on). When we are flying, we usually take it in turns to provide the aircraft and divide flying legs up dependent upon weather forecasts and to cater for any restrictions in force locally in respect of qualification levels.
We've carried out these trips almost annually for some twenty years now, in most cases with the original participants.