When I was a kid my parents pretty much always factored in some kind of historic thing whenever we went on long trips.

Yep. We did the same in Croatia, and spent a couple days exploring Dubrovnik city. However, I think Smallsteps was a little young to appreciate much of it, though she had fun.

Friends were just in the Canary islands, and while a great getaway for their purpose, it really is a "do nothing" kind of place for the most part.

You sit and wait for them to come and then they are gone in a flash and you have lost all those moments in between.

This is an interesting thought also. I remember reading a long time ago that planning a holiday is just as relaxing as going on one, and in some cases, more so.