I have a group I ride with regularly, but for twice or three times a year, we do a wandering road trip 
Always a different leader, who also books the night stops etc. Time on road varies subject to the trip & time of the year.
Our key to success is to keep the group under 12 bikes & NO WOMEN
We ride with our gals regularly, but for these boys rides, it removes certain parameters of the daily grind, without the need to be chastised & beaten by our better halves  
No clashes or arguments, but a lot of piss taking if you get us lost 
I think the key ingredient David, is to choose wisely who can go the distance & handle the heat 
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My memory is becoming that good, I should be able to organise my own surprise party soon
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