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How to Have More Fun When You Travel


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A few years ago, I met someone in Spain who was on a two-week trip across Europe. I asked them how much planning they’d done and they pulled out an Excel sheet that, from a distance, looked complex enough to be the entire financial backend for a successful startup.

Not everyone actually plans like this. But we do think that a lot of vacations end up kind of same-y, and a lot of people end up missing out on fun things, because 1) they don’t plan super well and 2) they don’t even think of doing some of the fun things they could do.

This is nobody’s fault — travel is something that most people don’t do often. Why should you be expected to be good at it? Plus, all the guidebooks and essays online more or less tell you the same thing. (The discourse has evolved to the point where some writers are publishing things like The Case Against Travel.)

Here are some of our ideas about travel that you may find helpful.

How to plan a great trip


The real Golden Ratio for travel planning is the amount of planning where:

  1. You won’t be stressing about logistics to the point where it’s a detriment to your trip.
  2. You have maximum flexibility to be spontaneous given #1.

Problem is, most people far overestimate how much planning they need to do to satisfy #1, which means their options for #2 are limited. This is how you get generic travel itineraries where everyone books the same restaurants and visits the same 8 attractions they saw on TikTok and reserved a month in advance.

Here is a selection of planning styles that should fit most people:

  1. Don’t even book stays or decide what cities to visit, just decide what airport to fly to.
  2. Decide what cities to visit, but don’t book stays yet.
  3. Decide what cities to visit and book your stays ahead of time (and maybe some restaurants).

Anything beyond that, save some specific exceptions, is generally too much planning even for people who get stressed about things not being planned. Many of the most enjoyable trips that either of us have ever been on fall into planning categories #1 and #2.

A couple of other counter-narrative ideas:

    • You generally shouldn’t book (a lot of) restaurants weeks in advance. Three reasons why.
      • Booking a bunch of your trip’s restaurants far in advance eliminates the magic of stumbling across a great spot, and it influences how and where you can spend your time on a day you have a reservation.
      • The FOMO you get from places like TikTok, Instagram, online essays etc. about ‘hard to book restaurants’ is often useless. For every restaurant that goes viral on TikTok, there are 100 more similar places that are just as good but haven’t had the misfortune of being put on blast by an influencer.
      • The extra-fancy Michelin star restaurants that you actually do have to book in advance are way more same-y across the world than normal, local restaurants. If you actually want to eat the unique and traditional food that locals do, you won’t find it at these $100+ per plate spots. (It can still be fun to go to these, though, so don’t feel bad about booking some.)

    • It’s really easy to trick yourself into thinking there are things you *need* to do and book in advance because you saw them online. The truth is that the internet is neither representative nor comprehensive about places, and so your perception of what there is to do somewhere is probably warped (if you’re getting ideas from Top 10 essays online, TikTok videos, etc).
      • The irony is that if you book a bunch of this stuff in advance and leave little room for serendipity, you could come away from your trip actually believing that the stuff you read about online was representative and comprehensive, because that’s what you did.

Fun and unique ways you could travel


Below is a list of things that most people don’t do on their trips, but could probably have fun doing. These are not in exclusion of the main tourist attractions, but they are other things you could consider doing that you might not have been told about.

Caveat: Some countries are more dangerous than others. Keep that in mind.

    • Design and complete a difficult mission (like the straight line series of videos)
    • Pick a start point and an end point for your trip, and plan nothing else (like this series)
    • Play a game, like a race across a country or tag across a continent (like this series)
    • See what you can get for $10 and make it a competition
    • Don’t allow yourself to spend time in your hotel (besides sleeping)
    • Go to local sporting events
    • Go for a long run, bike ride, or hike around the entire city
    • Do a cooking class in somebody else’s home
    • Try exploring without your phone or a map for an entire day 
    • As you wander a city, flip a coin to decide which direction you turn at each corner
    • Do an activity (hiking, biking, etc.) with a bunch of locals
      • You can often find these on online meetup sites or groups for the city
      • You can use Tinder/Hinge/Bumble/social apps to find people for all sorts of non-romantic things, too
    • Do a scavenger hunt but for food
    • Walk up to a random local and ask them what you should do in the area
    • Go to a local transit center and take the first/cheapest option available, no matter where it goes
      • Train station, bus station, airport, etc.
    • Play sports with a local
      • There are lots of apps that let you sign up to play sports (volleyball, tennis, etc.) with people
      • One benefit of this is you meet someone who can show you around/tell you about cool spots
    • Get a disposable camera 
    • Go to a concert
    • Decide what to do by manually searching through Google Maps instead of reading guides/posts
      • Guides online are what other people liked doing, you should find what you like doing
    • Figure out what local events are going on in the city and go to those

Why don’t more trips look more like some of the bullet points on this list? We don’t think it’s because people would enjoy the things on the above list less — it’s more that they haven’t been told they can or should do them.


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