Travelling with groups can be great fun; some are pricey; others not so much. In the end, it is the makeup of the group that makes or breaks the group experience.
For us, while we've encountered exceptions to the rule, generally speaking if the company is about cycling as a way to travel and explore, we enjoy the company of the group; if cycling is secondary to the "vacation experience", we find there is a higher the probability that you have group members that tend to be....uh...err...for lack of a better term...demanding. These are the type of people who are too worried about getting the most for their money than going with the flow of the trip. For example, we were in Spain, in the heart of the Rioja wine region and one of the guests was bemoaning to everyone and anyone his inability to get a good Scotch and how much it cost him for the mediocre one they sold him. Really? Try the Rioja, dude, it is fantastic!
But, I digress. Check with people you would like to travel with and see what groups they like. Make a list of what you're looking for in a trip. Going with a well known company like Trek Travel, Backroads, or Sojourn will probably guarantee you a well organized trip with great guides. But don't discount smaller groups. UW-Stevens Point Adventure Tours, Timberline and PAC Tour are some of our favorite groups--all seem to attract a fun group of people, although we've encountered that "demanding" guest on them as well although not as often. And, if you do encounter them on a trip, you'll be amazed at how, an early start on the road gets you away from them; and maybe a dinner on your own one night to escape....go with (or in this case, against) the flow and enjoy the trip.
Based on this thread, I'll be looking at Crankin's Cycling Country recommendation -- sounds like our kind of group. Thanks Crankin
2009 Waterford RS-14 S&S Couplers - Brooks B68-Anatomica - Traveller
2008 Waterford RS-33 - Brooks B68-Anatomica - Go Fast
2012 Waterford Commuter - Brooks B68-Anatomica - 3.5-Season/Commuter
2011 Surly Troll - Brooks B68 Imperial - Snow Beast