Riding w/ friends for the occasional same local route and same local venues I don't mind. Again 'occasional'. Last year I experienced another summer adventure - 11K / 6 wks. (No, I'm not retired). When I do these trips, and even the solo riding along PCH or in the mtns of So Cal, it's therapy for me because it clears my mind, lets me think and these times alone let me be more creative about bus, my life, my goals, etc., etc.
On my longer journeys, I generally have 1 of the women I'm sleeping with fly into an area, then she'll ride with me for about 3 days, then drop her off at another airport along the way. The women are always blown away about how much 'they see' of nature - and their minds become much clearer. Happens 'every time'. Last year, I had 2 different ladies meet me along the way. LOTS of fun. Simple 250 to 350 mile days thru 2 lane hwys / back roads. Btw, last year experienced a locally brewed 'Pecan Beer' somewhere outside of Albuquerque (I think). Still one of the best beers I've ever tasted.