Awesome. My version of this road trip includes boxing. I call them my FightOdysseys. I have done 3 big ones so far. My biggest to date lasted 3 months. I drove 16,000 miles around the US with my dog Rocky (yes, yes...my dog's name is Rocky...named after my idol, Rocky Marciano). I boxed 42 guys on that trip. It was an even mix of gay and straight guys. I bonded with every single one of them.
My buddies from undergrad and I go on a trip once a year. We plan this in advance, and it's just us--no wives, no girlfriends, no significant others, no children. Sometimes I worry that, as we get older, our trips will become less regular.
Last winter, on a dreary rainy night, I chanced to share a table in the pub with a group of four elderly ladies. They had been college roommates back in the Devonian Era, I believe, and met every year in a different city. This was something like their 25th or 30th time. Just bad luck that they spent it drinking beer with me. (They were at the coast the night before.) So it's possible.