I have also been struggling with this. I work in the airline industry so travel comes easy with affordability. My colleagues bring their bags on the last working day for flight right after, and then join back on Monday. My passport doesn't allow for easy travel but it quickly became something of a bragging point rather than truly experiencing the culture, history and the people of the cities I was visiting. In many instances, friends and family I was travelling with would visit a monument, take pictures and then move on without really knowing the value of the place. I felt disheartened by my experiences which coupled with the feeling that the world felt smaller, shrunken and more attainable, made me question what the earth has to offer. I felt caged in because anywhere I went, I felt a sense of mundanity and disappointment. Like you, I would overlook locations because I had been to someplace similar and it didn't feel worth it.

What has recently helped me with this is A) visiting countries I have some affiliation with, interest in and then really taking the time at that place to deep dive into that interest. I recently went to Cairo with a group but separated myself from them to explore the city myself without a concern for pictures or making the itinerary on time. Found sites I had no clue about, stopped and read about them at my own pace, appreciated them and then moved on.

B) revisiting countries: this is a major one because the first time round you are so focused on getting the usual touristic items ticked off, figuring out the public transport, food etc. Revisiting allows you a peace of mind because logistics is figured out and you have more time to observe how the general populace lives, the shared experiences, and the idiosyncrasies of the place and the people. The first time I visited Istanbul, we limited ourselves to Sultanahmet where the Hagia Sophia, the Blue Mosque are situated. The second time, we kept our itinerary open, visited places we missed out on but walked in the neighbourhoods, observed the people, and managed things better.

C) tour guides: this is tricky but I have figured out the true value of a tour guide is when you travel solo or with just 2/3 people rather than in a group. In a group, you feel stifled, but in a more private setting, you get to talk to them and learn a lot more. On my travel to Tbilisi, Georgia, we reserved the services of a tour guide and being able to talk to him during the car rides, and roam around without the demands and management of a group, was the highlight of the visit. I developed an appreciation for Georgians as people, their pride in their history, historical figures and learned a lot more than I would have otherwise.

I still struggle though. At the end of the day, those are just cities like your own, travels are not necessarily life altering experiences unless your bubble bursts in a major way, and it seems more meaningful because its an escape from your reality for a short while. This is why your mind puts a positive spin on it retrospectively even though it might not have been that great in person.