I have tried this a few times with people I don’t know. Being that I am a slower rider,the others always become frustrated and we only see each other at end of the day if at all.
I have come to the conclusion I am incapable of riding with others and don’t even attempt it anymore. Your results may be different but what happens to me is I can’t go faster and others can’t slow down, so it just endless frustration for all.
The other thing I noticed when riding with others is there is less interaction with locals. When alone I seek conversation with locals, when with others the tendency is to talk to each other.