Travel is usually seen and described as an easy ailment to any malaise. An instant life changing experience.
In reality, I have found travel to be hard. It is often boring, predictable and expensive. Coming across meaningful experiences does not happen automatically. Doing it “right” is hard.
I have found myself following these guidelines in an attempt to have more meaningful experiences, deeper conversations and chances at serendipity.
Planning much removes the chance for improvisation on your trip. You become rigid to your plans, and cannot adapt them based on chance encounters. On the other hand, traveling to a place blind does not do it justice. To appreciate a place you need to understand it.
Resolve this conflict by doing plenty of research but no planning. Make your research varied. Immerse yourself in the media of your destination. Listen to the music, watch the movies and TV shows. Watch documentaries about its history. Read books and magazine articles. Look up the recent news. Listen to podcasts about its nature.
This will take up your time and get you excited before you leave. You will land with a lot of inspiration but no set plans to tie you down.
You will not be able to finish all the content you find by the time you leave. This is perfect; you can bring it with you. Download the Netflix movies, local TV shows, podcasts, Spotify albums. Buy some Kindle books, save articles to your Pocket, and pack a paperback.
Travel inherently has a lot of downtime where you can consume this media: on flights, trains, bus rides, in coffee shops and restaurants in between people watching.
Before and during your trip you should feel immersed in the destination with this media.
Consume this media with furious curiosity, and let that guide your travels. If you happen to watch an interesting series about the parks of Tokyo, go visit those parks, not the temples. If you read a great book about Ottoman Cairo, visit the Ottoman sites, not the Ancient Egyptian ones.
Ask a lot of questions. How do the characters in this TV show interact differently than the local shows I watch? How does a place’s religious values affect the people’s behaviors?
Let your questions drive what you consume next, as well as what you will try to learn more about during your trip. Spend your time pondering them. Drive conversations with the people you meet towards answering those questions.
Give yourself a concrete achievable mission (or many) to drive your travel. Your missions will give you a sense of purpose; without them, it is easy to feel meaningless.
If you read about the history of tea in China: make a mission out of trying to find the best tea you can bring home with you on your trip to Beijing.
If you read about the sacredness of mountains in Japan: make your mission to find and spend time in a mountain temple.
Traveling for the sake of travel can get boring. Having a mission, no matter how arbitrary, gives you something to do outside of a top sites checklist, and introduces a good element of randomness in your plans.
Prefer missions that are simple and silly. Here’s a free one you can use for almost any trip: find a local bookstore and get an English book from or about the city you’re in.
Everyone’s amateur mistake is to try and see as much as possible with the time available. “I’ll do a 10 day Euro trip, 2 days per city in the top 5 capitals.”
Avoid this. Go slow, slower than you expect.
Keep your plan flexible enough that you can extend stays at locations that deserve it.
Take your time to take in a city and its atmosphere. Relax on rooftops. Walk around meaninglessly. It is difficult to do these things when trying to squeeze in the must-see and must-dos in a minimal amount of time.
For short trips, a good rule of thumb is to plan for five days in big cities and two days in small ones.
Consider bicycle touring as a way to force yourself to slow down. Bicycle touring means traveling from city to city by bicycle, with all your luggage packed on your bike. You can only move as fast as you pedal.
To get a sense of a place, you should have a sense of its layout. You won’t learn this by taking Ubers everywhere.
Walk around. Go to your destinations on foot and bike. Get lost. Look at maps.
Leave with a rough mental map of where your favorite things are.
When traveling somewhere you don’t know the first language, pick up some of it. Even if everyone understands English as well, try say your please and thank yous in German or Swahili.
Embarrass yourself at the coffee shop trying to order with a phrasebook. See how much of the foreign alphabet you can learn to read by the end of the trip.
In many countries, there are regions where the indigenous language is different from the national one. Learn the common greeting in the local indigenous language, and see if anyone understands your butchered pronunciation.
Have a good balance between going to new places and returning to the ones you’ve most enjoyed. Your second and third time there will have a different taste and meaning than the first. Build a relationship with the city. Observe how it changes over time.
Treat traveling as a skill like any other. Do not expect to be perfect at it immediately. Appreciate that you are getting better at it over time. And have fun