My Travel Philosophy


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I’ve always been a planner.  I think you can probably blame my dad for that – I remember going on road trips when I was younger and having an itinerary down to the quarter-hour.  I grew up thinking that we had to maximize how much we did in a set period of time because time is limited/we traveled all the way here, may as well do something/what if I never come back/I don’t want to miss out on any opportunities … basically, I understood FOMO about 15 years before it was a cool hashtag.

I adopted my dad’s travel philosophy as a proxy because I didn’t have enough experience to form my own yet. However, now that adult-me has taken over a dozen trips, both with and without friends & family, I have finally figured out what my travel philosophy.

My travel philosophy may not be right for you! Everyone has a different travel style and it’s something that takes some experience to really figure out. Hopefully this post helps to clarify what kind of traveler you are!

The Downfalls of Overplanning

A few years ago I traveled to Italy with my boyfriend at the time.  He had never been that into traveling and it was my first time in continental Europe (Iceland was my first European country.)  I was so nervous about this trip because I wanted him to look forward to traveling as much as I did.  This anxiety transformed itself into an obsessive need to plan the perfect trip.  If I didn’t plan the perfect trip, he may not enjoy himself! If the trip wasn’t perfect, he may not want to travel again!

Long story short, I tried to micromanage the hell out of this trip.  I wasn’t exactly planning the itinerary down to the quarter-hour, but I could tell you pretty much exactly what the plan was by day and by time of day.  I had pages and pages of research.  Maps of the local cities in Tuscany.  Rail schedules.  Weather forecasts.  Pins dropped into my Google account.  A folder with all of this printed out with tabs by day.


Makes me cringe just thinking about it.

To his credit, my ex-boyfriend was a really laid back guy.  He didn’t particularly care about the plans, he was just going with the flow.  But me… well, I cared about the plans.  We HAD TO DO ALL OF THIS.  EVERYTHING ON THE LIST.

I was stressed.  It made him stressed.  We didn’t live for the moment but for the list. 


I think I was afraid that not doing something on my list would lead to regret. I think I was afraid that I wouldn’t enjoy this trip if I missed out on anything. Unfortunately, this meant I was focused on “what’s next?” versus “what’s now”?

I call this “checklist traveling“.

What is “Checklist Traveling”?

Checklist traveling is what happens when you mix FOMO with excellent planning. You’ve carefully researched everything to do in a city. You know best times to visit the top sites, the cutest cafes mentioned by all the bloggers, and all the coupon codes for booking skip-the-line tours. You practically know the city as well as someone who has actually been there and you want to experience it – ALL. NOW. On THIS trip.

You would think that my experience in Italy would be enough to teach me that “checklist traveling” isn’t the way to go, but nope, I repeated it when I backpacked in western Europe. I started off in Paris which is basically the worst city for a checklist traveler.

Eiffel Tower – check.

Notre Dame – check.

Champs-Élysées – check.

Macaron – check.

I lived and died by my checklist. I did not sleep in a single day in Paris.  Not one.  The latest I slept was 7:30 am, and it made me feel guilty! Sleeping in meant I wasn’t doing something – sleeping in meant I was wasting my time!

Needless to say, I didn’t enjoy Paris at all. And I think it’s because I was a newbie traveler still figuring out my travel philosophy.

My First Experience Traveling Without a Plan

Thankfully I got a breath of fresh air on my stop right after Paris: Ghent, Belgium.  A sleepy town even without being compared to Paris, it was the first place that didn’t really have a checklist.  I remember sleeping in until 8:30 my first morning there and it was wonderful.  Nothing (specific) to do, nothing (specific) to see, just wandering.

While in Ghent, I took a wonderful free walking tour, drank as much Trappist beer as I could handle, tried every chocolate shop I could find, explored streets without a specific direction, hunted for artistic graffiti with a woman I met at the hostel, explored the local castle, bell tower, and church, and read books while occasionally people-watching.  Certainly not “exciting”, but it was the breath of fresh air I needed on my trip.

The planner in me was anxious that I didn’t have plans. What would I do? Would I get bored? Would I miss out on something?

I’m sure I missed out on something in Ghent, but I KNOW I missed out on things in Paris. I followed my checklist and still didn’t do everything. That’s when I learned something critical about traveling:

A few days – even a week! – are not enough to properly experience an entire city. Any trip is going to give you a snapshot, a glimpse, into that city. Unless you immerse yourself in a place for months – even years – you won’t see & experience everything that one place has to offer.

All this to say: my travel philosophy has evolved with experience. 

My Travel Philosophy

From my experiences, I have learned that I need to have a balance of seeing, doing, socializing, enjoying, and relaxing to really enjoy my trip. 


Yes, yes, sightseeing is what checklist travelers do.   But the difference here is that a checklist traveler plans their entire trip on sightseeing.

You can’t visit Paris without seeing the Eiffel Tower. You can’t visit Rome without seeing the Colosseum. But in a city that big, you can’t expect to visit every attraction AND enjoy your trip. Prioritize!

My Travel Philosophy: Seeing (the Eiffel Tower)


Sightseeing actually isn’t doing anything. Stopping and looking at something pretty or famous is a pitstop, not an activity.

I’ve learned it’s important to get out there and do something at least a little bit physical.  I loved the Eiffel Tower, but I almost never talk about it.  It wasn’t an experience, it was a pitstop.  What I do talk about, however, is what I did on my trips.  My Wachau Valley wine tour outside of Vienna (below) is still the best thing I’ve ever done.  Riding bikes through the crisp autumn air in between glasses of sweet white wine with new friends is way more fun than seeing a painting or looking at a cool clock.

My Travel Philosophy: The Wachau Wine Valley Bicycle Tour

I remember being slightly buzzed, zipping down a steep hill, laughing with my newfound friends on our way back to Vienna. The Eiffel Tower is gorgeous, of course, but it didn’t make me feel alive. Doing something will give you that.


This is more directed at solo travelers since people traveling with companions will have a social aspect built-in.  I am an extrovert with introverted tendencies, which generally translates to “I can make friends, it’s just not super easy.”  If you’re traveling alone, find ways to make friends.  For most, that can be done at the hostel.  For me, that usually means finding a group to drink beer with or meeting cool people on tours I take. 

I’ve found that taking tours is the best way to meet people. I met a lovely couple on that wine tour I just mentioned, and we ended up meeting up again in Budapest! During my walking tour in Prague, I met two women who invited me to dinner and we still keep in touch. I had a similar experience in Savannah during a graveyard tour. Try new things and figure out what works for you!


Let’s be honest, this means food.  I didn’t want to call it “eating” because that sounds gluttonous, but that’s what I mean.  Black truffle pasta in Umbria, fondue in Zermatt, stroopwafels in Amsterdam, Sacher torte in Vienna – mmm.  Delicious.  Food is just as much of an experience as anything else, so plan on trying that street cart, ordering a bottle of wine at lunch, or splurging at the nicer restaurant for dinner.

I’m not exaggerating when I say there are some meals that I remember more than some of the famous sites I visited.

One excellent way to combine socializing, doing, & enjoying is to take a cooking class! I’ve done that three times now in Italy and once in France. I actually don’t like cooking but it gives you the means to be social while eating wonderful food, doing something interactive, and learning the local culture.


Traveling is stressful and exhausting.  You really need to selfishly prioritize yourself a little bit and take the time you need.  Sleep in a bit instead of taking the first train out. Go back to your room and watch a movie.  Read a book on a park bench.  Sit at a bar and sip local beer while browsing on Facebook. 

Remember how I said I felt guilty in Paris for sleeping past 7? I’ve been able to drop some of that guilt now. I don’t like sleeping in too late, and I don’t want to waste away my entire trip by doing nothing, but I have learned to recognize that relaxing is important for keeping the entire experience balanced.

Developing Your Own Philosophy

I think everyone’s travel philosophy will start with these building blocks. You don’t need to figure out how much of each is right before going. Just pay attention to what you want and be able to pivot. All I ask of you: do more than be a checklist traveler!

And, remember: what you need may be different from what your companions need.  It is perfectly ok to separate for a few hours to fulfill separate needs.  If your traveling companion(s) want a nap but you want to walk by the river, do it! You aren’t wrong, but neither are they.  If your companion needs some alone time, grant it to them, without being offended.  Be a little selfish and allow your companions to be selfish, too. 

4 thoughts on “My Travel Philosophy”

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