Wifey B: Interesting question.
I spent a decade doing a fair amount of traveling for the AOA. Most of the time I was spending time with my colleagues so not as much chance to spend time with the locals.
However, very often I would get to a city the evening before the work started and would go out and have a meal by myself, and the same would be true after the work was over and I would be waiting to head to the airport. I have found that ever since I was a kid, I actually enjoy having a meal in the local restaurant/diner by myself. Most of the time the staff will engage you in conversation and you can find out a lot about their experience in the city or town you are in. The best time for this is eating a late dinner, which I would often do after flying East to whichever city I was in. Late dinner they aren't busy but aren't necessarily looking to close up.
When on the boat, I don't get those opportunities because I am usually with my wife and she doesn't like having conversations with random strangers. However, she does like to sleep in and I wake up early. So I walk the town, find a coffee shop or diner and have some coffee and maybe a breakfast and chat up the locals. That is not the same as really spending a few days in a location however and meeting more folks as the two of you seem to be able to do.
FWIW, I like solo road trips for the same reasons.
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