There may be an inverse correlation between how much money you spend on travel and how interesting the trip is. Some of my fondest memories are of trips where I slept in my car, which I did earlier this summer, and hitchhiked. The few trips I took staying in all-inclusive five-star hotels I hardly remember at all.
Some of the best restaurants are cheap. Expensive restaurants everywhere tend to cater to the same international clientele and therefore aren’t particularly interesting. The same goes for hotels. Almost all hotel chains, and increasingly also most alternative accommodation options like Airbnb, have become indistinguishable between different locations. There are still interesting niche hotels, but they’re mostly cheap and involve avoiding the highest-rated properties. Cheap hotels and hostels also tend to attract more interesting travelers, so the chance of getting into good conversations there is higher.
It’s similar for experiencing the outdoors. In my experience, there is no correlation between the amount of money spend and the profundity of nature experiences. All it takes is not being a wimp and a few hours to hike off the well-trodden paths. Mother nature is democratic that way.
If not money, what determines how interesting our trips are? I think it’s about having the nerve to do unusual things, and time. Of course, “interesting” isn’t the only thing that matters for travel. Money probably helps with other dimensions like comfort, but even for those, too much money may have adverse consequences.