Should You Keep Going Back To The Same Places Or Take Trips Somewhere New?

Tyler Cowen lays out different theories for where you should travel, arguments for traveling deeply, returning to the same places and getting to know them well, or traveling broadly to get a taste of every destination?

He offers a greater explanation of each, but here are his options:

  1. Prioritize those countries and regions you haven’t visited yet.
  2. Get to know some of your favorite places truly in depth
  3. Try to visit “events,” especially temporary events. (Like, go to Lviv now.)
  4. Do more trips with the friends you value most, and go wherever will maximize their interest and participation.
  5. Figure out…where you really don’t want to go. Then go there!

I don’t have a goal to ‘visit every country’ for its own sake, but spending time somewhere gives me context to better understand a destination. There might be more value in visiting Ukraine now, paying attention to where to go and how to do so safely, to come back better-informed than just doom scrolling Twitter on the topic.

I’m not strategic in saying I want to return to one place over and over versus returning to someplace I’ve been, preferring to discover what my future self wants to experience at the time I’m planning a trip. I don’t have a bucket list.

Instead I’m a bit more serendipitous – factoring ideas my wife has, things we might do that will interest our daughter, and great deals or award availability tip the scales. That can also mean going back to the same place over and over (my wife loves France, and though skipped 2021 we’ve gone every year otherwise for many many years) as well as returning to other favorites.

Sometimes the point is to do something we wouldn’t otherwise think of doing, for instance I’ve been to India many times but who often says they want to visit Chennai without family or friends there, business, or a conference of some sort? It was a part of the country we’d never been and that was good enough.

The number one element of my travel philosophy is that I travel enough not to worry about seeing and doing everything in a given place when I visit. If I want to, I can return, there’s no need for a ‘forced march’ through everything to see and do in a place. I don’t do slow travel per se but also don’t feel pressure to ‘get it all done’ on a single visit.

There are places I haven’t been back to, but that’s not because going back isn’t an option – if I want to see something I missed out on badly enough I will go back. And if I don’t – if it wasn’t worth the flight and time and prioritization – then I probably didn’t miss out on that much to begin with.

There are some places I don’t want to spend very much time in, but I do want to visit. That’s what stopovers are for! The archetypal example of this, I think, is Doha.

I’m glad that I’ve been but I wouldn’t want to spend a week or return over and over. The Museum of Islamic Art is worth seeing, not just for the items from everyday life in the 12th century but for the context of the building itself, I.M. Pei’s last design where he rejected every proposed location and had them build on a purpose-designed man-made island.

Sometimes it’s about change of weather, going someplace warm when it’s cold or going someplace cold for cold wwather activities. But when there’s no particular thing dictating your choice, how do you choose to the extent that the entire world is your choice set? Are you maximizing new experiences or familiar ones?

One thing that I found is that I was skewing more towards the familiar after spending over a year inside the U.S., and as more and more countries opened up. I felt like I needed to return to places I’d been – it had been longer than it might otherwise have been. I needed to visit family I hadn’t seen, revisit the familiar places I loved to eat and experience. If you haven’t been to a place in years it feels more new, and you already know you’ll love it! So I’m only now just returning to thinking about new experiences.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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Comments

  1. I like to go to the familiar places and new places too. The repeat trips have something you missed from the last time. You enjoy it so much it’s fun to do it again. Food is a big part of trips for me. I like the comfort foods from home and I like to try new, local stuff too.

  2. Most people don’t like change so they go somewhere once and unless they have a bad experience tend to go back to the same places. Personally I like visiting Europe so I go there mostly. There are other places I think would be very interesting but either due to distance or food preferences I doubt I will go.

    Once you go somewhere and you learn how to use public transportation or rentals cars and get used to the food choices, etc. people prefer not to do that all over again since it can be stressful for people not on the road all the time.

  3. I used to go prioritize new places… but having visited around 60 countries, a lot of my travel is going back to places that I know I love (I try to visit Bora Bora, Switzerland, Maui, and Colombia every year and then the other trips I take are often newer places). Still so much of the world I want to see, but the “new” places will be more off-the-beaten path for me and harder to visit while working remotely.

  4. It’s a “What are you actually planning to do?” question. Because if you just want to go some place warm and comfortable to kick up your feet and have some nice food in a beautiful beach, it’s not a bad idea to just find a spot that works and keep going there. Going to different places to do the same thing just because is silly. If you JUST want a resort, going to the Maldives and Hawaii and Aruba and Cancun and a dozen other locations really only offers so much more to the “I want a resort” crowd.

    If you want to see sights or experience cultures, cuisine, and do new things, then go new places.

  5. I love seeing new places, but there’s a certain nostalgia going back to the same places and meeting the same shopkeeper or bartender year after year.

    One such story involves the middle-eastern cafe on Upper Road near Agricultural Hall in the northern part of London, aka Angel Station on the Northern line.

    I would have a nonprofit conference there every year, always on July 4th (yes ironic!), And I would always stop there to pick up exactly three cans of ‘real’ Diet Coke in the morning. He was always there, we always talked and by the third year he had a huge smile on his face when I walked in one year later. And that repeated for years.

    Sadly, COVID 19 has stopped that conference, but I am looking forward to meeting my friend again soon.

    🙂

  6. @ Gary — Both new and old are great. Major hubs are easier, so we tend to visit those the most. We also get superior treatment at hotels we have visited many times, which makes us want to return to those places yet again. We’ve been to India once, and we have zero desire to return. The air is filfthy, so no thank you.

  7. You raise some interesting questions, Gary. I suppose the answers are based entirely on one’s experience and philosophy of travel. I know people who are terrified to leave the U.S. and never have, some who made trips to Europe and got absolutely nothing out of it, and others who return to the same foreign resorts over and over again, never seeing a thing of the countries that they are in. On the other hand, I also know many people who want to, or have, traveled to many places and on a continuum from where they are reasonably comfortable (Europe, say) to moderate and then extreme conditions, occasionally returning to familiar places somewhere along this line.

    Personally I’m towards the further group, after a “grand tour” of Europe as a teenager in the late ’60s. And then after college did the Hippie Trail overland from France to Nepal, and then I went on as much as possible by surface transportation across Australia and Latin America. That jaunt took me a year. And I still do as much travel as is reasonably possible, time and money permitting, usually with the intention of hitting new places. Because who knows if they will accessible again (Afghanistan was beautiful, but this isn’t a great time to return!). I got my wife doing this somewhat too, though she never let me forget that I dragged her to Albania, but she is willing to come back with me to Oman. On the other hand she was just fine when I hied off alone to China, Andorra, Haiti and Antarctica, among other places. So I’m up to 122 countries now.

    Those of us who love to travel can’t really explain this to those who don’t, and it’s probably not worth trying. But sometimes…sometimes when a reluctant traveler comes along they suddenly discover that the experience is worth it. And my opinion is that everyone whose mind is opened by travel is one more person who not only will enjoy more of this world, but will be less likely to accept what they are told about it without asking deeper questions.

  8. Both. Some places I can (and do) visit over and over, for example: Japan. It’s just so amazing.
    Some places I have no desire to visit again, for example: UAE, Qatar.
    Other places – many places – I have no desire to visit at all, for example: Iraq, Lybia, Russia, Congo (quite a few more).
    And after all of those – are the places that I’ve never been, and would love to see, but not putting any “pressure” on myself. If it works out – great, if it doesn’t – I’m not stressing over some FOMO.

  9. I always say there’s a difference between “traveling” and “vacation”. Typically, the former is somewhere you’ve never been and you have a laundry list of things to do and see. “Vacation” is normally somewhere you’ve already been, or more often an all-inclusive/cruise-type experience that is definitely meant more as relaxation than “traveling”.

    @Jon I completely agree. There are some areas I’ve traveled to that just felt “right”; it was more the day to day life there than the sights to see. Nothing like returning a few years later to the same familiar shops and restaurants, seeing the same owners/staff and reminiscing

  10. We definitely try to mix up the two. One of our favorite things is returning to a beloved place but we equally love the excitement of the new. After this recent forced travel hiatus our upcoming international travel reflects our philosophy: Guanacaste for the 5th time, our first African Safari and a train trip through one of the only places in Europe we haven’t ventured- Scotland.

    We often think of our first trip to a place as a “scouting trip.” Like you we don’t feel pressed to see everything. If we love it we will be back.

  11. Interesting article Gary. When I first started to travel internationally I used to believe that I always needed to visit a new country instead of returning to places I have been. That logic turned out to be a mistake and lasted until I started visiting places like Japan and China. China is soo large and varied that you can’t see it all in one trip and it worth going back to over and over again. Japan on the other hand is a smaller country but I find the culture very interesting and very deep.

    I found myself returning to those countries over and over. However when I plan an overseas trip I try to incorporate not only new areas of a country I have visited before but also new countries. Funny enough on this trip I will have a stayover in Doha. Am I totally pumped to visit Qatar? Not really. I’ve done Dubai and been to Istanbul etc, so I have a bit of context of what to expect but I still think there is value in seeing it. I also still plan trips to countries I have never visited. When the war is over I wish to visit Ukraine. Israel/Egypt/Jordan is high on my list. South Africa and other parts of Africa. It is a whole continent that is unexplored for me that I have an interest in, so I will mix completely new country trips in with returning to places I have been. No need to deny yourself returning to places you really enjoy, although there is growth in pushing yourself to explore new places and to give them a chance. I really liked Vietnam and didn’t think I would. I felt kinda bleh about Japan after my first trip there but now it is one of my favorite places the more I have gotten to explore it. Gotta give places a chance.

  12. What is so bad about Chennai? That is my “go to” place in India.

    After building up a collection of new places, I now value some previously visited places over new places. For example, I would rather visit Paris than Kinshasa even though I’ve never been there and have never seen the wide Congo River.

    As far as Japan, that’s an interesting country. I used to view Japan as an enemy country but with fewer and fewer political allies and the war having ended more than 75 years ago, it is time to bury the hatchet.

  13. @derek – Did you view (W) Germany as an enemy at the same time or for as long as you viewed Japan as an enemy?

    Just curious…

  14. I’d gotten into sort of a rut – rotating London, NYC, Tokyo, DC – which are cities with endless things to do. I am visiting South Korea next week – something a bit less familiar – a little more anxiety due to the unknown isn’t always bad.

  15. I love these types of philosophical discussions, and this is a great one. Thank you, Gary! I also do both. I definitely have a couple of places that I’ve visited several times but make sure to do something new or visit a different area in the country or state when I go. This is a very interesting question and one that I’ve been thinking about a lot as I plan my travel this year and going forward.

  16. I agree with Barb. It’s a very interesting discussion that we ourselves reflect on regularly. We’re returning to London in a few days, but that’s a place that most certainly is worthy of multiple visits.

    On a recent visit to Italy, we checked out the heel of the boat, a region we’d never touched on multiple previous visits. We’ve visited more than 75 sovereign countries but have no interest in adding to that particular score. We just keep the number handy in case anyone wants to ask. Still, we just made it to Indonesia for the first time, thanks to a bargain business class fare, and enjoyed blissful days in Bali. We try to balance between new and return visits.

    It’s great to read the perspectives of other active travelers.

  17. That should of course read “heel of the boot.” I can’t even blame autocorrect for that one.

  18. I was keeping a Google sheet list of my countries visited and somehow when I hit 102 I accidentally deleted it. I was proud of myself for breaking the century mark but at the same time I started to feel burdened by the continued feeling of always needing to rack up new countries (which gets harder and harder to do as you visit more and more.) After a while I decided not to redo the spreadsheet, so I could just continue to travel and go wherever I want without feeling it “doesn’t count” if it’s not a new country. I’m definitely not the guy who’s going to go back over and over to the same hotels and same cities even but it’s fairly ridiculous to think after you’ve spent a few days or a week in one country (usually mostly in the capital) you’ve “been there done that”. I’ve been trying to let myself go back and explore the countries I love more, like Malaysia, Italy, eastern Europe. It’s a bit liberating to get out of the country list contest mentality

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