My 3 Travel Guidelines

wing of a planePlanning a trip

Recently I was helping my mom, aunt, and their 2 friends plan their trip to New York. My mom's task was simple: find the right plane ticket at the right price. Naturally, as the family's de facto (and UNPAID!) travel agent, that task was given to me instead. And so marked the beginning not just of her trip, but mine as well. 

Generally speaking, my life is well-organized. I'm disciplined, have good impulse control, and know how to say "no" to things that will take my money...with one exception. Travel! I'm the world's biggest sucker for good airfare deals. Knowing that I can find dirt cheap (if not free) accommodation everywhere I go, airfare is usually the deciding factor when it comes to my travel destinations. 

I lived in China for 2 years. I lived in Japan for 1. I've traveled around Asia, Europe, and many parts of the United States. But somehow, some way, I had never been to the east coast (minus Florida). How could I let such a brazen gap in my life as a digital nomad remain?! Answer: I couldn't.

Travel: A Part of My Life

See, what happens is something like this: I'm casually browsing Facebook, reading a recent blog post, or helping someone find airfare when suddenly BAM!! It finds me, or I find it: a ticket that is too good to pass up. And in a matter of minutes I've gone from having an open calendar to planning my next getaway. That's what happened here.

working at a deskAllowing me to search for airfare deals is like dangling little baggies of drugs in front of an addict. Sure, there's a chance I won't bite, but don't bet your money on it. While searching for the best tickets in June I discovered something surprising: flights from St. Louis to New York (and DC) weren't bad in May! I ignored the baggie long enough to get their tickets booked, and then quickly grabbed my dose and ran. 

Framework for Traveling

As the first post about one of my trips, I'd like to focus primarily the overarching guidelines and ideas that govern my travel. Sometimes I wish I were the kind of person who could throw caution to the wind, show up at a destination unhindered by preconceptions, and let the river of freedom take me wherever it flows.

But I'm not. Not even close. I like having plans, and I like making them even more. But don't cry for poor, rigid me just yet. In truth, I have no problem breaking plans...once I'm on the ground. In fact, I do it often. But for me to arrive without anything in mind is a tragedy of Greco-Roman proportions. That said, there are people who can pull off that kind of spontaneous trip. I'm just not one of them.

So now that we got that out of the way, let's begin!

#1: Structured days and free nights

As I mentioned, I'm a guy with a plan. And I like that. But I'm also a relatively seasoned traveler. This is shorthand for "plans change". 

I have two guidelines for making plans: 

  1. Make a plan
  2. Don't worry if it changes

tropical beach paradiseLet's say that I'm going to Thailand for 2 weeks. I already know that it's often cheaper to book things in advance. In preparation for this trip, I spent $65 to reserve my spot on a boat tour to islands nestled in a sun-soaked water paradise. Better $65 now than $90 later!

Now the day I've been waiting for arrives. Paradise, here I come!

But that morning I meet some incredibly interesting travelers in my hostel. They tell me how they're taking a full-day backpacking trip into the forest to walk with free-roaming elephants. For $60 I can hitch a ride with them, be taken through the tropics with their local guide, eat lunch and dinner with them, and of course see elephants in their natural habitat. 

Which to do?! Many people would assume that I would naturally stick with my non-refundable $65 boat ride. I mean, I'm practically the dictionary definition of a penny hoarder. But this is travel, and that changes everything! You see, I'm strict with my money during normal days so that I can be free during travel days. My first thought isn't, "Well, what is the right thing to do financially?" Rather, it's, "What do I want to do, given that I'm in this remote village on the other side of the planet, a place I may never see again?" 

Regardless of which I choose, I won't feel any stress about the decision. $65? Who cares. I'm in Thailand! I haven't been waiting for that boat ride as much as I've been waiting to have the time of my life. Here, opportunities trump money. 

elephant hike in Thailand

Thailand - Summer 2016

It's worth noting that I'm rarely in this situation. Usually I'm happy with what I've picked out, the people I'm staying with are also doing it, or nothing more interesting comes my way in time. If this happens once or twice during your trip, just go with the flow. 5 years later you're not going to give a damn about that those 60 or 100 bucks, but you WILL remember seeing a wild elephant through the thick green foliage of a Thai rain forest. 

Now, for nighttime. Most tourist attractions are closed at night. Most travelers also have the bulk of their free time at night. Nighttime = free time. Hang out with new people, casually stroll around the night markets, and relax!

#2: Walk!

Manhattan hiking on my tripFor better or worse, I'm highly sedentary most of the week. Though I sporadically engage in short-lived bursts of cardio and the occasional hour in nature, you can usually find me working and studying at my desk. It's not that I'm a bonafide couch potato, but that I have a lot of interests, hobbies, and work that are best done sitting. 

Which is why I like to stay as mobile as possible during my trips. If I have the option to walk or take a bus, I'll walk. I prefer taking in the destinations with long breaths instead of panting gasps. I like the serendipity of finding a scenic view, eating at a cozy restaurant, or an unexpected chat with locals. 

In fact, this has become such a prevalent feature of my trips that I now schedule full-day walks (assuming it's a place where that's worthwhile). I did this on my most recent trip to New York. Granted, this particular walk was a little extreme, but it seemed suitable for a city of extremes. 



#3: Learn something 

rotunda in dc museumEvery trip is different, and each destination on the trip has something unique to offer. Nonetheless, I try to learn things everywhere I go. An interest in history, culture, and architecture can leave you spiraling down into a sea of curiosities and new information...which I love!

If there's a worthwhile museum, I'll go. If there's a free walking tour, I'll join. If there's a class about local cuisine or wares, I'll take it. I always aim to walk away with something more than just a pretty memory. Need ideas? Groupon is a good place to start! 

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Thanks for joining me! Until next time...

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One Comment

  1. I’m the same way with plans! I plan obsessively before I go and then don’t mind if everything changes the second I get there. Love it 🙂

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