Most people suck at traveling: 9 principles to travel well

Witsi Einstock

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Most people suck at traveling: 9 principles to travel well<br>If you're not a little lonely you're doing it wrong

Itsi Weinstock<br>Apr 24, 2026

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I consider myself to be in the 99th percentile of being good at travelling. It’s a skill you can learn. I feel like no one teaches people this stuff.<br>I think most people fall in one of two failure modes:<br>Paying a lot and being very comfortable and seeing major sites and activities

Getting drunk on hostel circuits and generally traveling-to-party

Both ways you’re leaving life on the table. Travel is at the core of the human spirit, most of us are a long way from where we started in Africa. You should do it well.<br>Of course this gets harder when you can only have very short holidays or travel with a family, but I think versions of the same principles apply.<br>If there is one meta-principle to follow: maximize surface area . You are in an entirely new cultural context and you want as many opportunities as possible for new experiences to hit you. Serendipity is the name of the game. This is why you also should avoid planning much at all.<br>1. Go somewhere where YOU are interesting

You want people to engage with you. If you go where all the other tourists go then you will have no luck and have a boring time. People will be disingenuous with you and not discriminate between you and the other walking dollar signs. Usually random people love to see tourists and show off their culture, their town, and their friends to the new person. It’s because having someone new and curious around is interesting and fun.<br>Every list of best things to do in every city is wrong. As an exercise, look up Tripadvisor for your own city. It likely sucks big time. And you, the resident, are probably not inclined to go there and meet a random tourist.<br>Ideas:<br>Go to any place not on a main tourist trail. That’s like 99% of places.

Do not do any professionally planned activities at any cost.

Go to countries that are less frequented.

Go to popular places during the off-season. I went to the Amalfi Coast with a friend in winter and had a local come up to us, drunk, and ask “what the fuck are you doing here”.

2. Travel should be cheap

Australians have a reputation for traveling a lot, we go to very inexpensive places as a rule. Americans don’t travel as much despite being more wealthy and numerous. I think a lot of them are pricing themselves out of travel. Often things are better because they are cheap. When things are expensive there’s an extractive relationship that makes it hard to deeply relate with the person or experience you’re having. The best places I’ve ever stayed have been a few bucks and I hang out with the owners.<br>The biggest expense of travel should be having to pay for your own rent while you’re away, followed by the flights. You will have a far better time if you go to places where you have large purchasing power. You can treat yourself luxuriously in Vietnam and still pay less than just existing in Paris. A good meal in India costs 50c.<br>Part of this is that you can be more generous. Buy coffees and dinners for people you meet. A great way to ingratiate yourself is to go to a market and buy some fruit and pass it around to kids, everyone will love you.<br>Stay in the cheapest place possible modulo no bed bugs. You are not trying to stay in your room so this is something silly to prioritize in any case. In cheap places, you will also find other people who know how to travel. Hostels are great.<br>Couch surf!

You can stay with random people who want to meet you and interact with you AND it’s free. It’s in fact only able to be so good because it’s free. I usually alternate between couch surfing and staying in hostels. Hostels let you meet more people to travel with. Couch surfing is higher variance but you definitely get some of the best experiences. The optimal is when a couch surfing host hosts multiple people at the same time.<br>The main platform, Couchsurfing, sold to private equity and has been getting shitter since 2013, I have written many articles about it. I cofounded Couchers.org in 2020 as a nonprofit alternative, I see maintaining this as a core piece of civilizational infrastructure. If there aren’t enough people on Couchers you have my blessing to use Couchsurfing.<br>If you are a woman and are worried to use this, consider that it is probably safer than a hostel and also you can just stay with other women.<br>Hitch hike!

Great surface area move. I have met some great people, and had incredibly good experiences. Even when you can’t speak the same language it’s a lot of fun. It’s definitely slower to get around this way but can be well worth it.<br>You won’t get murdered as much as you think.<br>3. Don’t try to sleep with people

Aiming for travel romances and hookups is an enormous distraction. Every time I meet a guy who starts just talking about girls I leave because it’s boring.<br>Many...