Through the years, I have on occasion met others and ridden for a short way, or for days and even weeks.
One thing I find after the suggestion comes up, is to agree that whenever, and for whatever reason or no reason at all, that either one can simply say ”I think it’s time to go back to riding alone”… and that both are cool with that 😊
I have done several tours with a friend and former co-worker, and also have done some solo trips. And two ACA trips. And two Europe bike trips with REI Travel. (Side note: REI Travel is canceling all trips, no longer doing trips.)
While I like the companionship of traveling with someone, there are a lot of things that can go wrong. When you are traveling solo, if you want to change the itinerary or schedule, you are a committee of one, change it without argument. If traveling with someone, the committee that decides may have a tie vote.
Do you plan to travel together during the day, in which case you both should have the same desired pace and stamina. Or do each of you have your own navigation equipment so you can make sure you can make your destination without problems? And of course desired distance is an issue to decide every day.
Are you both at about the same level of fitness?
Are you cooking as a group or individually? If as a group, there is opportunity for conflict.
And of course do you both have the same desire for frequency of motel vs camping?
If you are traveling with someone and you each have your own equipment (tent, cooking gear), if you want to split up during the trip, no problem, you can. If you are sharing equipment, you are locked into a group.
After I did Pacific Coast with a friend, I decided not to do another trip with him. And then, three years later we did a Florida trip together, I again decided to never do another trip with him. And six years later we did Natchez Trace and we both had enough arguments that this time I am most certain that we will never do another trip together. We are still friends, but, no more trips.
On one of my solo trips, I met a gal at a hostel, we were both going in the same direction for a while, we traveled together for two days. It was fun traveling with someone I met along the way. If you are on an ACA route, there is the chance you will meet others in campgrounds, etc.
When it comes to traveling with someone, you are much less likely to have arguments about who is doing most of the work if you have a goal of doing 20 percent more than your partner.