The Secret to Happy Travel

A pathway through the Foliage Garden at the Singapore Botanic Gardens

Rule #1: Don’t talk about fight club. Know thyself.
Rule #2: Know thy travel partner.
Rule #3: Do not expect to change.

Every travel blogger has their own take on questions like “Should you book everything in advance?” “Where should you splurge and save on travel?” “Is XYZ ‘worth’ it?”

Here’s the secret: There isn’t one right answer to how to have an amazing, positive experience while traveling. The real key to enjoying yourself is to know yourself, know the person (or people) you’re traveling with, and be at peace with the reality of who you both are.

What’s right for everyone else, might not be right for you: An example

I have always been a “book in advance” person, but this is a pretty unpopular preference in the long-term travel world. Many contend that keeping your plans open can save you money and leave you free to change your schedule at the last minute. “You can decide to stay longer in one place! Leave early if you don’t like a particular city! Travel with a group of new friends!” Here’s the thing: In 9 months of travel none of those things ever once happened, so I finally decided to banish this fantasy of trying to be a different person than I am.

For me, booking travel in advance prolongs the joy of the trip itself (I get to fantasize about the trip and then I get to take it! Win-win!), eases any worries I may have about missing out on things I want to do, and helps me feel safe and secure in a foreign country. For example, we decided to make Vietnam our first experiment with traveling without booking/planning in advance. This didn’t work for us! We wasted precious time trying to choose tours or activities while we were in the country, paid extra for open-date bus tickets, aimlessly wandered the streets of at least a couple towns trying to find a room (sweating and bickering the entire time, of course), and still managed to screw up our timing and not get to spend any real time in Hanoi.

Whether to book in advance or not is only one of a million ways that your personal travel style will impact how you should plan and execute your travel.

What to consider when planning your trip

  • What are you trying to get out of your travels? If all you want is to unplug and relax, you officially have my permission to book an all-inclusive resort and go sit your buns in the sand.
  • Are you a worrier? OK then, take the time to research safe bus companies in advance, and maybe accept that you’ll never enjoy driving scooters through the hills of Thailand or Vietnam.
  • When do you enjoy being awake? While not actually morning people, both Alex and I really like the feeling of getting up early and having the whole day free for activities. We often take very early flights for this reason. But this won’t work for everyone — do not put yourself through missing flights if you know you won’t wake up!
  • Do you like meeting and talking to strangers? This is a big, fat “no” for us, so we scrapped the fantasy of meeting up with a cool group of travelers who we were going to spontaneously decide to travel with.
  • Do you enjoy planning travel? I love it. It’s like a drug for me. Why would I choose to forego the joy of planning a trip in advance? (Just to be clear, I don’t obsess over an hourly schedule — more like the number of nights to spend in a place and how to get from A to B.)
  • Does unplanned time make you feel free and liberated or just anxious? For me, it’s the latter.
  • What are your personal interests or favorite activities? Food, art, architecture, history, politics, shopping, hanging out with friends, reading, volunteering — these are all great subjects/activities you can focus your travels around. If you don’t like museums, you won’t suddenly like museums in another country. We didn’t like crowded bars or clubs in NYC, so why would we love the backpacker party scene in Amsterdam?
  • Are you a loner? Do you like making new friends? I don’t think anyone should feel like there’s something “better” about being a solo traveler, traveling as a couple, or making friends on the road. Everyone enjoys different social dynamics.
  • What kinds of splurges feel “worth it” to you at home? If you get in bed every night and thank the sweet Lord above for your 1000 thread count sheets, hosteling might not be for you. If you love indulging in craft cocktails/fine dining/music festivals/you name it, those are probably the same things that are going to feel “worth it” to you abroad, too. Invest in those experiences.
  • Is money actually an issue for you? There is no glory in traveling as cheaply as possible. If you have the money, why not spend it? (See also: You’re Never Going to Travel Like a Local)

And here’s the real kicker about all of these considerations: You have to take your travel companion(s) into account, too. For the many months we were planning our trip, I tried repeatedly to get Alex excited about itinerary planning. But seriously, it’s just not his thing. It wasn’t that he wasn’t excited for the trip or he didn’t care. He just doesn’t get a sick joy out of cruising Kayak or AirBnB like I do.

Similarly, while I know Alex and I can and will get ourselves up early as often as we need to, when traveling with friends in Croatia this summer, I had to accept that while we could rouse ourselves once or twice for an early morning in extreme need, I should mostly count on sleeping in and taking a good hour or two to get up and out in the morning. Trying to mold the person you’re traveling with into a different person is a recipe for enormous frustration for all involved.

Whatever your natural proclivities — whether you’re a planner/bargain hunter/early riser/culture lover like me or the exact opposite — you have to know and accept that you’re not going to suddenly change when outside your normal environment. (If anything, your natural tendencies are likely to become more pronounced.)

If you’re not sure what kind of traveler you (or your bestie you’re about to spend 3 months on the road with) are, test the waters. Try a weekend jaunt unplanned. Go camping and see how you do. Try to make friends with strangers. Be honest with yourself about whether you enjoyed it. Often I’ve found myself browsing the web for articles validating the kind of travel I felt was right for me. If that’s you right now, this is it: I officially give you permission to travel your way, whether your way is like mine or not.

Leave a Reply

Your email address will not be published. Required fields are marked *