I flew my R44 to Morocco a couple of years ago and returned via Portugal. Spain and Portugal work well. I landed at Faro which was perfectly friendly but there is quite a bit of bureaucracy to manage and it is not cheap. The smaller private airfields are fine, had no problems at all. It is probably true that after Morocco Portugal and Spain seemed wonderfully simple, but that is because I calculated that in Morocco one needed to allow at least one hour of bureaucracy management for every hour of flying. The desert flying was amazing though.
I did not land off airfield in Portugal on that trip but I understand that it should not be a problem with landowners permission.
In Spain you can land off airfield but you need permission from the Spanish CAA and the land owners. You can contact the Spanish AOPA for help on 00 34 3451 0387.
All internal flights in Spain and Portugal require a flight plan!
You really need to buy the Jeppersen/Bottlang trip kit for the countries that you are passing through it has all the info you need.
Finally remember that in these countries where on the whole things work pretty efficiently there is still a slightly different attitude to the fine details of the rules. Summed up by the thought that, like parents, they should be respected but not slavishly obeyed. Personally I think that they have got that right!