About Rick Steves, I was not aware that he operates tours until I went to his Web site just now. I have only watched his shows and checked out his books from the library.
I have not taken any organized tour. It's ironic that Rick shows how people to travel on their own, and yet offers motorcoach tours. Are they the same 10-cities-in-14 days like I have seen advertised, or done better? I have relatives who went on such motorcoach tours, and came back not remembering even the name of the places they had been to. And they still thought it was fun!
For me, planning for a trip is half of the fun. I read up on the places, their histories, the local culture. Then, how to get around using the local transportation, where to stay, what to see, what special food and drink they have, etc...
A trip preparation usually begins with checking out from the local libraries all the DVDs and travel guides that are available. Then, I cull down to one travel guide that I would take with me. I also supplement the above with research on the Web.
Some friends teased me that such seemingly detailed preparation take all the spontaneity out of a trip. I beg to differ! There are always plenty of surprises, as things never work out like you plan, and I have stories to tell. As for flexibility, I always try to allow myself plenty of time for sightseeing, and am willing to drop some planned stops to have more time to linger. In other words, less quantity for higher quality. No 10 cities in 14 days here.
The above said, I can see myself taking tours in places that are a bit more tourism-challenged. In fact, even some civilized nations such as Japan can be difficult to navigate on your own if the local speaks no English, and you can't even read the street signs.