I've considered touring with a touring company on occasion, but found them to be quite expensive. A less expensive option is to tour with a touring club. For example, Alberta has two touring clubs: Elbow Valley Cycling Club (based in Calgary) and Edmonton Bicycle Club (based in Edmonton). Manitoba has one touring club. BC has at least one. The state of Victoria in Australia has a whole bunch.
These cycletouring clubs have lots of day rides, a few weekend tours, and usually at least one longer tour each year. You pay the club membership fee which will allow you to ride the day rides and maybe some weekend tours. And then you pay a reasonable fee for the longer tours.
Through the day rides and tours organised by the club, club members get to know each other, get to know each other's touring style, and then form small groups to go off and do other tours together, independent of the club. During the winter, the clubs often have "show and tell" nights where the club members who have done this tell everyone about their tours all over the world.
(I did the Golden Triangle tour with the Elbow Valley Cycling Club two years, and a Logan's Pass hub-and-spoke tour one year, and they were all good tours. It was nice to ride with a group of people for a long weekend, to have my camping gear shuttled from one stop to the next, and to be provided with heaps of good food.
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