Les Veloistes Gentiles are a group of friends who ride together round France periodically. This year they took on the Pyrenees, including the Tourmalet. A great idea if you can convince some more sap to follow you round in a truck with your bags in the back.
If you have never taken on some proper cycling mountains in the Alps or Pyrenees, you have to go one day. I think a lot of riders think they will never make it up, given the kind of rides they normally train on, but my experience of working as a guide in some big mountains is that it is astounding what a bit of application and a very small gear can do for you when faced with the steep stuff. There are now lots of organisations which also organise these kind of trips such as Veloventoux and Pyractif which can make sure your trip runs smoothly.