The joys of randomness in travel, the moments of genuine connections with people and cultures, are so much more rewarding than ticking off sites to see. But I think this is a lot easier to do when traveling solo. When I travel with others, I feel obligated to give them the experience they feel they need to have to justify the time and expense.
For instance, when I took my friends to Ireland in 2022 (I had been three times, they had never really been outside the States), we majored on visiting the big sites: Book of Kells in Dublin, Glendalough, Rock of Cashel, Cliffs of Moher, etc. All of these places are worth visiting (well, maybe give the Cliffs a pass at this point), but we all felt like we had been at "Ireland Epcot" for ten days. The only Irish folks with whom we interacted were in the service industry and had no real interest in speaking to American tourists. It all felt a bit packaged and sterile, and I think we all felt it would have been nicer to spend a few days in a smaller Irish town just living -- visiting the pubs, the markets, the churches, and wandering wherever whim took us.
I contrast this with my solo trip to England that same summer. I intentionally chose to base myself in Shropshire for three weeks, since it's a very rural and sparsely populated county. While I did sight-see, I spent most of time just wandering the countryside, hill-walking, and exploring villages. I never planned out a meal, instead just picking a pub wherever I happened to be. (I needed a car for this trip.) I encountered so many lovely English people while walking, dining in pubs, attending church services, etc. This was far and away a more memorable and rewarding travel experience and has set the tone for what I expect out of a trip going forward: go for at least three weeks, spend your time in one place, and don't plan things out with too much detail.
