Travel philosophies for the well-traveled

How should you choose your next trip?  I can see a few general philosophies on the table:

1. Prioritize those countries and regions you haven’t visited yet.  For me that might mean Montenegro, Lithuania, Bangladesh, and Saudi Arabia.  But the downside is waking up one morning and saying “Hey, what the hell am I doing in Sardinia!?”

2. Get to know some of your favorite places truly in depth, most of all major cities that are easy to reach and often are connected to free or paid invitations.  For me that would imply more trips to London, Paris, Tokyo, Berlin — you get the picture.  Under this view, the returns to variety are diminishing.  And have I ever regretted stopping in on those places?

3. Try to visit “events,” especially temporary events.  Right after the Berlin Wall came down, I did a big car trip around Eastern Europe.  Loved it.  Perhaps these days I should be stopping in at Neom, flying to Lviv, and so on.  Those historical moments will never be recaptured.  And usually such trips are memorable.

4. Do more trips with the friends you value most, and go wherever will maximize their interest and participation.  You already know the world, people are what make life special, and now it is time to “give back” your expertise.

How to decide!?  WWGPTS?

There is also the approach I discussed with Nabeel:

5. Figure out, within the bounds of safety and reasonable expense, where you really don’t want to go.  Then go there!  Expectations and surprise are everything, right?  And how else are you to develop a truly diversified portfolio?  Won’t you this way learn the most?

I am indebted to Ben Casnocha for a relevant conversation here, though without holding him liable for any of these views.

Addendum: GPT-4 opts for #3:

As an experienced traveler, if I were to pick only one of the philosophies, I would choose to visit events and historical moments (Philosophy 3). The reason for this choice is that it allows for unique, once-in-a-lifetime experiences that capture the essence of a particular time and place. Such trips often become memorable stories that you’ll cherish for a lifetime.

By prioritizing events and historical moments, you immerse yourself in situations that reveal the true character of a destination and its people, as well as provide valuable insights into the forces that shape societies and cultures. Additionally, this approach can lead to a greater appreciation for the world’s interconnectedness, as you witness firsthand the impact of global events on different regions.

While this philosophy might not cover all aspects of a well-rounded travel experience, it offers a powerful way to engage with the world and create lasting memories that will enrich your life beyond the confines of a single trip.


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