How to Travel: 21 Contrarian Rules


(Photo credit: Moyan Brenn)

This is a tactical post on travel from Ryan Holiday, who’s written on this blog before about the pragmatism of Stoicism and lessons learned as Director of Marketing for American Apparel.

To his 21 rules, I’ve added a few of my own tricks. Please share your own rules and tips in the comments!

Enter Ryan Holiday

Why are you traveling?

Because, you know, you don’t magically get a prize at the end of your life for having been to the most places. There is nothing inherently valuable in travel, no matter how hard the true believers try to convince us.

Seneca, the stoic philosopher, has a great line about the restlessness of those who seem compelled to travel. They go from resort to resort and climate to climate, he says, and continues:

“They make one journey after another and change spectacle for spectacle. As Lucretius says ‘Thus each man flees himself.’ But to what end if he does not escape himself? He pursues and dogs himself as his own most tedious companion. And so we must realize that our difficulty is not the fault of the places but of ourselves.”

It’s hard for me see anything to envy in most people who travel. Because deep down that is what they are doing. Fleeing themselves and the lives they’ve created. Or worse, they’re telling themselves that they’re after self-discovery, exploration or new perspectives when really they are running towards distraction and self-indulgence.

Is that why you’re packing up your things and hitting the road?

Not that I don’t travel myself–I did my fair share this year alone. Both coasts of Australia. I was in Amsterdam for a speaking gig (and I found myself at a tulip farm with Tim where he caught a chicken with his bare hands). I researched for my next book in Rome. I went down to Brazil. I went to Copenhagen. I spent enough time in New York that it felt like I lived there. I road tripped across the United States more times than I can count–New Orleans to New York; New York to Miami; Miami to Austin… The list goes on. If there was a chance to go somewhere I’d never been, I tried to take it, especially if it was historic.

But are you, as Emerson once put it, “bringing ruins to the ruins?”…

The purpose of travel, like all important experiences, is to improve yourself and your life. It’s just as likely–in some cases more likely–that you will do that closer to home and not further.

So what I think about when I travel is that “why.” (Some example “whys” for me: research, to unplug, a job or a paying gig, to show something that’s important to me to someone who is important to me, etc.) I don’t take it as self-evident that going to a given famous place is an accomplishment in and of itself. There are just as many fools living in Rome as there are at home.

And when you make this distinction, most of the other travel advice falls away. The penny pinching and the optimization, the trying to squeeze as many landmarks into a single day, all that becomes pointless and you focus on what matters.

I am saying that saving your money, plotting your time off work or school, diligently tracking your frequent flyer miles and taking a hostel tour of Europe or Asia on budget may be the wrong way to think about it.

In the vein of my somewhat controversial advice for young people, I thought I’d give some of my thoughts not just on traveling but on how to do it right.

My 21 Travel Rules and Criteria

1. Don’t check luggage. If you’re bringing that much stuff with you, you’re doing something wrong.

[TIM: I second this and encourage you to take things to extremes. Here’s exactly how I travel the world with 10 pounds or less.]

2. Instead of doing a TON of stuff. Pick one or two things, read all about those things and then actually spend time doing them. Research shows that you’ll enjoy an experience more if you’ve put effort and time into bringing it about. So I’d rather visit two or three sights that I’ve done my reading on and truly comprehend than I would seeing a ton of stuff that goes right in and out of my brain. (Oh, and never feel “obligated” to see the things everyone says you have to)

[TIM: Need some inspiration? Here are my highlight lists for Tokyo and Buenos Aires.]

3. Take long walks.

4. Stop living to relive. What are you taking all these pictures for? Oh, for the memories? Then just look at it and remember it. Experience the present moment. (Not that you can’t take photos but try to counteract the impulse to look at the world through your iPhone screen)

5. Read books, lots of books. You’re finally in a place where no one can interrupt you or call you into meetings and since half the television stations will be in another language…use it as a chance to do a lot of reading.

[TIM: I strongly suggest that non-fiction bigots (which I was for 15+ years) read or listen to some fiction to turn off their problem-solving minds. Try The Graveyard Book audiobook or Zorba the Greek.

6. Eat healthy. Enjoy the cuisine for sure, but you’ll enjoy the place less if you feel like a slob the whole time. (To put it another way, why are you eating pretzels on the airplane?)

[TIM: If you want to follow The Slow-Carb Diet, my default cuisine choices in airports are Thai and Mexican food. Also, keep a *small* bag of almonds in your bag to avoid digressions in emergencies.]

7. Try to avoid guidebooks, which are superficial at best and completely wrong at worst. I’ve had a lot more luck pulling up Wikipedia, and looking at the list of National (or World) Historical Register list for that city and swinging by a few of them. Better yet, I’ve found a lot cooler stuff in non-fiction books and literature that mentioned the cool stuff in passing. Then you Google it and find out where it is.

[TIM: I like to spend an afternoon visiting hostels, even if I’m staying in an apartment or hotel. The hostel staff will know which free and low-cost activities get the best reviews from the non-museum-going crowd.]

8. I like to go and stand on hallowed ground. It’s humbling and makes you a better person. Try it. (My personal favorite is battlefields–nothing is more eery or quiet or peaceful)

9. Come up with a schedule that works for you and get settled into it as soon as possible. You’re going to benefit less from your experiences if you’re scrambled, exhausted and inefficient. Me, I get up in the morning early and run. Then I work for a few hours. Then I roll lunch and activities into a 3-4 hour block where I am away from work and exploring the city I’m staying it. Then I come back, work, get caught up, relax and then eventually head out for a late dinner. In almost every time zone I’ve been in, this seems to be the ideal schedule to a) enjoy my life b) Not actually count as “taking time off.” No one feels that I am missing. And it lets me extend trips without feeling stressed or needing to rush home.

10. When you’re traveling to a new city, the first thing you should do when you get to the hotel is change into your work out clothes and go for a long run. You get to see the sights, get a sense of the layout and then you won’t waste an hour of your life in a lame hotel gym either.

11. Never recline your seat on an airplane. Yes, it gives you more room–but ultimately at the expense of someone else. In economics, they call this an externality. It’s bad. Don’t do it.

12. Stay in weird-ass hotels. Sometimes they can suck but the story is usually worth it. A few favorites: A hotel that was actually a early 20th-century luxury train car, a castle in Germany, the room where Gram Parsons died in Palm Desert, a hotel in Arizona where John Dillinger was arrested, and a hotel built by Wild Bill Hickok.

13. Read the historical markers–*actually* read them, don’t skim. They tend to tell you interesting stuff.

14. Add some work component to your travel if you can. Then you can write it all off on your taxes (or better, be paid for the whole thing).

[TIM: Here’s how an entire family moved to a tropical paradise in Indonesia and continued to earn income.]

15. Don’t waste time and space packing things you MIGHT need but could conceivably buy there. Remember, it costs money (time, energy, patience) to carry pointless things around. (Also, most hotels will give you razors, toothbrushes, toothpaste and other toiletries.)

16. Go see weird shit. It makes you think, shake your head, or at least, laugh. (For instance, did you know that there is a camel buried in the soldier’s cemetery at Vicksburg?)

[TIM: If you go to Japan, don’t miss the incredible Ghibli Museum, made by animator Hayao Miyazaki and located in Inokashira Park.]

17. Ignore the temptation to a) talk and tell everyone about your upcoming trip b) spend months and months planning. Just go. Get comfortable with travel being an ordinary experience in your life and you’ll do it more. Make it some enormous event, and you’re liable to confuse getting on a plane with an accomplishment by itself.

18. Regarding museums, I like Tyler Cowen’s trick about pretending you’re a thief who is casing the joint. It changes how you perceive and remember the art. Try it.

19. Don’t upgrade your phone plan to international when you leave the country. Not because it saves money but because it’s a really good excuse to not use your cellphone for a while. (And if you need to call someone, try Google Voice. It’s free)

20. Explore cool places inside the United States. The South is beautiful and chances are you haven’t seen most of it. There’s all sorts of weird history and wonderful things that your teachers never told you about. Check it out, a lot of it is within a drive of a day or two.

[TIM: Here are 12+ gems of the Pacific Northwest, encountered on a road trip from San Francisco to Whistler, Canada.]

[TIM: 21. OK, this one’s from me, just because it’s so much fun. Take pictures of yourself jumping in different places! It can turn a boring “adult” afternoon into a giddy kid-like experience. The below is from Burning Man 2010.]

(Photo: Mike Hedge)

In other words…

Travel should not be an escape. It should be part of your life, no better or no worse than the rest of your life. If you are so dissatisfied with what you do or where you live that you spend weeks and months figuring out how to get a few days away from either, that should be a wake-up call. There’s a big difference between *wanting* a change in scenery and *needing* to run away from a prison of your own making.

To me, there is more to admire in someone who challenges their perspectives and lifestyle choices at home than in some Instagram addict who conflates meaning with checking off boxes on a bucket list.

[TIM: I’m a fan of bucket lists, but different strokes for different folks…]

So ask: Do you deserve this trip? Ask yourself that honestly. Am I actually in a place to get something out of this?

Over the years, I feel like I have mastered the art of something I wouldn’t call “travel.” I’d call it living my life in interesting places.

These rules and tricks have helped make that possible, and maybe they’ll work for you, too.


What rules and tools have worked for you? Please share in the comments!

(A much shorter version of this piece, without my comments, first appeared in Thought Catalog.)

If you’ve ever fantasized about taking time off to globe-trot, I would highly recommend Rolf Pott’s Vagabonding. It is one of only two books I took with me when I traveled the world for 18 months. Outside Magazine founding editor Tim Cahill calls Vagabonding “the most sensible book of travel related advice ever written.”
I recently partnered with Rolf to release the exclusive audiobook for Vagabonding. For more on this incredible book, click here

Posted on: July 14, 2013.

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210 comments on “How to Travel: 21 Contrarian Rules

  1. For me, it’s taking the time to disconnect (over and above not using my phone). not checking emails or going online. The point is to enjoy the place, not replace the life you had at home with the same tasks but in a different surrounding.

    I too am a fan of travelling light. Can’t remember the last time I checked in luggage – what a chore!

    Awesome tips – talking to hostel staff about things to do is great !

    – Razwana


    • Well said Razwana! Travel is indeed a time to disconnect.

      However, I disagree strongly with Ryan’s assertion that “most travelers . . . are fleeing themselves and the lives they’ve created. Or worse, they’re telling themselves that they’re after self-discovery, exploration or new perspectives when really they are running towards distraction and self-indulgence.”


      If I’m running away from anything, it’s that I’m running away from things I don’t enjoy that much, like:

      – A boring life
      – A standard 9-to-5 job
      – Living in the same place all the time
      – Monotony
      – The 3-weeks-of-vacation-per-year job

      But that’s a negative way of looking at what I’m doing. What I am really doing is running TO things I love:

      – Seeing places that few get to see
      – Learning about the world, geography, life
      – Enjoying the beauty of our planet
      – Exploring cities, villages, and wilderness
      – Understanding the differences and similarities across humans
      – Speaking foreign languages
      – Camping in remote areas

      Today I wrote a whole blog post about this because Ryan’s comment irked me.

      Still, I agree with many of his other excellent points.


  2. A few additional tips that might help:

    1. Use couchsurfing to find locals to show you around – on my recent trip using hostels I got really tired of just hanging around westerners all the time

    2. Totally agree with no checked luggage! I managed 2.5 months in SE asia with only a 46L pack (this is about the biggest size that you can fit in a carry on space)

    3. Regarding #19 – Google voice – WRONG!!!!! Be very careful here! Google voice when making calls dials a US phone number and then transfers you. This will result in very expensive long distance bills. Use Skype for calls, but you can still use Google voice for text messages (or apple’s iMessage if you are careful that it doesn’t drop to “green” for regular SMS’s)


    • I’ve been using Google voice for the past year and a half and I never had to pay when calling US and Canada.

      If you’re using Google Voice with your mobile phone you can make calls for free using the free GrooVe IP Lite app. Just make sure you use the GrooVe IP app itself to make the call (it connects to your Google Voice account) and not the Google Voice app.


  3. What do you do to avoid getting infested with bedbugs as a frequent traveler? Also, what are your thoughts about listening to audio programs instead of reading books during waiting time?


      • I couldn’t disagree more about the bedbugs comment. I’ve traveled off and on in Southeast Asia for four years and stayed in $4 a night places. I never got bedbugs. They’ve been found in nice hotels as well. I think you just have to chalk up the possibility of dealing with bedbugs as a risk that might be taken while traveling. Just know what you’re going to do if it happens such as taking all your clothing to a laundry mat and even having your bag cleaned.


    • Bed bugs leave nasty stains on the bed frames that are easily spotted. Prior to paying for a room, ask to see it, and lift the mattress to check for dark brown stains.


    • A small piece of urinal block in your pocket works well (preferably retrieved from the janitor’s closet, rather than the urinal), but black pepper scattered on the bed also works.


    • I like to download a bunch of podcasts or audio books that I haven’t kept up on to listen to while on the plane, on public transportation or driving in a rental car across midwest states to see family(lots of farmland, not too exciting). Also lyric-less music like regular classical music, movie scores, jazz or something fun like Keiko Matsui type stuff kind of enhances travel without added lyrics interrupting thoughts.


  4. Great tips Ryan (and Tim!)

    My tip – you CAN travel with KIDS!

    It does makes things more interesting and accommodation a little more challenging, but the rewards are HUGE! We spent 8 weeks in Italy and France (we’re Australian) and took 3 small suitcases (NOT checked!) It was the most amazing thing to do together.

    Now we are planning a US assault!


  5. Constructive criticism for the author:

    “To me, there is more to admire in someone who challenges their perspectives…than in some Instagram addict who conflates meaning with checking off boxes on a bucket list.”

    “Over the years, I feel like I have mastered the art of something I wouldn’t call “travel.” I’d call it living my life in interesting places.”

    Yikes! Maybe mastering the art of a self-deprecating joke here and there would lighten things up a bit.

    I definitely second the tip about eating healthy when traveling abroad. I think it helps to make the trip an energizing experience upon returning home.


    P.S. I really like Neil Strauss’s talk on writing from his Creativelive with Tim.


  6. Thanks for the guest post Ryan, lots of great tips which are so easy to forget when you’re daydreaming of travel plans.

    My favourite one was definitely the long walks. There is nothing like getting lost in a foreign city and just wandering around for hours, immersing yourself in local culture and staying away from the other tourists. Many fond memories of doing this in different places.


    • Definitely love the walks. I should also mention: this is a great thing to do where you live RIGHT NOW. Love walking around so-called “familiar” environs until I find something totally unfamiliar.


      • Very true Tim! When you’re in Sydney for the seminar I recommend doing that around Newtown. Fantastic food, culture, art, etc.


    • I once took a walk in unfamiliar area. It was quaint historic place. After taking rights and lefts. I ventured in a darker place. Suddenly, I felt out of place. I took look at those ladies lined up on corners of intersections. I just realized of what I read up about the area I was exploring. I stumbled in the notorious streets where the shemale streetwalkers making a living.

      I went from the birthplace of American to shemale streetwalkers. Definitely a timeline of America evolution.


    • amen to wandering around. I have enjoyed impromptu music, learning new games with locals, milking a cow in the core of Rome, the joy and exuberance of elections in a newly independent country, local foods (and beers), and more, simply by striking out away from the madding crowds.


  7. Here are some tips I have on sleeping while traveling:

    With so many changing sleep environments it is essential to create a fool proof system to be able to sleep anywhere anytime, below is my system. The system might change a little depending the environment but this post will cover the essentials:

    Light blocking

    1. Eye Mask

    The eye mask is really the best tool for blocking light. Your face structure will depend on which mask works best for you. I have gone through a few. If you fly business they usually give you a pretty decent one, or you can pick them up at most airports.

    2. Hoodie

    Hoodies are an essential tool for traveling on planes, ideally zip up. Not only do they keep you warm and can be used to block light by putting the hood over your eyes (make sure hood is big enough to do this) but they are also great because you can hide your headphones without the flight attendants seeing that you are still listening to an electronic device (you will see why this is important below).

    P.S. I have not turned my electronic devices off on the last 40 flights I have taken… Don’t worry, you won’t bring down the plane.

    Noise Cancellation

    White Noise App

    This is a super hack. The White Noise App is available for both iOS and Android costs around $2 (there is a free lite version too) but is totally worth it. Even for 1 nights good sleep, $2 is a small price to pay, but for countless nights sleep, the value is infinite. Possibly the highest ROI app I have ever purchased. Get some quality noise cancellation headphones (sport headphones work well to if your roll around in your sleep a lot), close your eyes and listen to the world fade away. Use this in conjunction with a hoodie on flights, and sleep right through the safety announcements, takeoff and landing to get a sold extra 30-45 min sleep on a flight.


    Gentle Alarm

    I currently use this on my Nexus 7 tablet and really like it. It allows you to wake using any music on your device, I have it just play randomly from my playlist, it fades in music so you are not woken suddenly, it tracks your sleep patterns if you keep your tablet on your bed while you are sleeping and only wakes you when you are in a light sleep pattern within your given window and it makes you do math problems to turn it off!

    There you have it. With this combo you will be able to sleep through the next world war and wake up fresh for work on Monday.

    Liked by 1 person

      • I set every station of FM2 on my car radio to. 89.5 – all static. Ive experimented on my daughter and predictably she reflexively covers her ears, a reaction everyone feels because it sounds like angry hornets.

        like brillopad for the ear drums, I love what i hear after listening to big bang static, or god static for the deistic.


  8. I’m a big believer in slow travel as it give you the opportunity to really get to know the people and culture in a country. When you stay in a place for a few months you can learn the basics of the language and actually communicate with locals.

    It allows you to connect with the people who don’t speak any English at all and that makes all the difference. For example ordering your noodle soup in the local language from a street vendor or haggling on with a vendor on a night market.

    Even if you only speak the basics of the language the locals will treat you completely different. It removes a cultural barrier and creates a much deeper connection.


  9. Good tips Ryan. Gave some really meaningful insights for traveling and adding value for the journeys. Agree with you on, do not just take photos and miss the moment to see the pics later. Something I was doing a lot in my European travels. When I think back the last Scotland trip, I feel I need to go back and live the present and experience the beauty again as I missed by taking a hell lot of photos to share with others :)

    Thanks for the share, loved reading.


  10. Interesting take on travel, and great tips. However, number 11, don’t recline? Hogwash. Reclining is a function of the seat that you purchase. The person behind has the same option to recline. That being said, I’m 6 foot and on a rare few flights I’ve asked the person in front to not come all the way back because I literally couldn’t fit. Daytime flight, I might slightly recline. If I want/need to sleep, I’m reclining. If someone asked me not to, daytime flight no problem, night flight I’d accommodate briefly but explain they needed to ask a flight attendant for another seat.


    • I might recline one or two notches. Had a man in front of me once who wanted to recline as far back as the seat would go. I asked nicely for him to move up some, he refused. We almost came to blows as he was a total jerk. Took some gentle persuading, but he finally relented. At 6-2 250, size can be a big help.


    • I completely agree. Especially on long flights, we need to recline the seat to sleep. I would flip that rule around and say that everyone should be required to recline their seat after takeoff. Also, non-reclining seats should be removed from all planes.


      • You don’t NEED to. You like/want to and it comes at the direct expense of the person behind you. Go for it–it’s perfectly legal–but let’s call it what it is.


      • Ryan,
        “let’s call it what it is”. What’s that, “selfish”? In typical “bleeding heart” fashion, Ryan Holiday has perched himself on the moral high ground and deemed what everyone NEEDS, because he’s “self-less”. Do something as mundane as to use the functionality of the seat, and the only conclusion is “your selfish choice has directly affected the comfort of the person behind you”. No grey area. Don’t consider your own comfort, ignore your back pain, on a red-eye and need to sleep, too bad, if Ryan doesn’t NEED to recline, well let’s just call you what you are…


      • Sorry Ryan, I NEED to. I have a herniated disk in my lower back (due to a surgery). The slight upward tilt of the plane while it is flying transfers all of the weight onto that disk. The only way to get the weight off the disk is to recline. I also use lumber support, take meds as needed. But the biggest preventive measure against mutli-day back spasms is reclining.
        I hope that you can stay injury-free and NEVER have to experience that kind of pain.


      • Remember, dudes: If you want (or have determined that you NEED) more space or creature comfort, just ask for last-minute free upgrades to first class. Or spend 15-20 minutes researching which plane models on which airlines consistently have the most space, in the form of: fewest tickets sold = more leg room, larger seats in coach, smaller aisles may mean more elbow room, etc… Also when given the option, I always reserve seats in an exit row or immediately in front of, as there’s more space there.
        In any event, find the airline that most consistently flies the planes that suit you, then book with them exclusively (and become a preferred customer). Then if you’re price-conscious, book those seats on those planes on the times/dates that make the most sense.
        Easy peasy.
        Or use a free trial on something like Zirtual to do this research for you.
        Also try to remember that Ryan is offering a lot of principle in his ideas. Typically in economics (as he references), but also in life in general, it’s healthy and practical to have more of an abundance mentality – acknowledging that there is more than enough for everyone, and you haven’t necessarily hurt or stolen opportunity from someone else if you’ve gained in your own life. But, externalities are an exception here. Just be conscious of that.
        Remember, anytime you sacrifice your own creature comforts for the sake of another, you’re making big deposits into the Karma Bank, others will notice and be more inclined to reciprocate and/or pay it forward, and you’re practicing self-discipline (which of course is an important practice in any venture toward bettering ourselves).
        Safe & adventurous travels to you all!


      • Happy medium: “hey, do you mind if I recline my seat? I’d like to be a little more comfortable, but don’t want to cramp you up too much.”


      • I’m 2 meters tall and when somebody reclines that makes my life miserable for the duration of the flight. Yes, I’m trying to get an exit row seats when it is possible (they are hard to get; most often there is some shorty relaxing his short legs in the exit row),


    • Matt,
      By your logic I could do knock you down, cut you off, step on your foot, etc. because, hey, we all have the same option. How about the virtue of courtesy and respect for others?


  11. “To me, there is more to admire in someone who challenges their perspectives and lifestyle choices at home than in some Instagram addict who conflates meaning with checking off boxes on a bucket list.” +1

    I understood this when I was working abroad, thinking that a “cultural change” was the perfect escape of my boring life at home.

    1 month later I discovered it was not about living abroad or at home, because if the lifestyle was the same (corporate job life), everything was the same.

    It was about changing my perspective and defining my core values and priorities in life.

    Now I am freelancing and developing personal projects, and despite I could go back into the corporate world in a future, the fact of changing my perspective, defining my goals, and living a different lifestyle, is providing me a better experience than any rtw trip for just the purpose of escape (although I must say I love travelling for that purpose also).


  12. Thanks for these tips!

    I especially agree with pack less, and go for runs / long walks. While staying in the walled city of Lucca, Italy, the run each morning around the top of the wall was magic.

    Additionally, take long walks in your own neck of the woods. We were designed to walk, it feels great, and chances are you will discover something new.

    With aloha from Hawaii Island,


  13. I head for a place where i know friends and ask as many as possible people
    Whats the best place they know in their country.
    I did it when i went to sao paulo and planning to go rio afterwards and everyone sugested me to go to florianopolis instead. Florianopolis was amazing.


  14. Well, most people take a vacation abroad as a time off.
    The biggest Tip from me is try and not use your Internet connection, looking back you’ll see that world kept going and Facebook stuff wasn’t that interesting, free your mind to enjoy the “now”.

    Sam G


  15. Thanks for the post Ryan.

    A tip I would add
    – Instead of bringing maps and guide books with you, take a photo of them and just zoom in on the photo you took when you need directions.


  16. Quite thought provoking.

    FYI there’s a typo before “japanese animator”, should be “by” instead of “my”


  17. I travel because I get to explore. Everything is new and I feel like a child. I also love to meet new people from different cultures.

    Recommendation for no.16: Go see weird shit.

    You must see the Salvador Dali museum in Figueres (near Barcelona) – strangest shit I’ve ever seen


    • Agreed! One of the most pleasant days I’ve ever had was spent in a hotel in Richmond-on-Thames in England at an open window watching the people and the houses and the cars, while listening to music on my headphones. It was a blissful, peaceful moment at the end of a long trip.