While I’ve been incredibly fortunate to travel to some breathtakingly beautiful places in the world, it’s more than a vacation. It’s a learning process. About the world, certainly; but perhaps more importantly, about myself.

Here are some of the things that I’ve learned along the way…

Zig Where Everyone Zags

Above: Zigging way off the beaten path in Myanmar.

Allowing yourself to zig where everyone zags and wander intentionally pays off big time no matter where you go. For me, this has paid off exceedingly well in Oman, Bali, Mongolia, and Myanmar, but also in nearly every other place I’ve visited. Below are a couple approaches that I’ve learned to make the most of getting off the beaten path:

Travel to places that are physically hard to access via car/motorbike/boat/local bus/train.
Start from a known place of interest, then using the logic of the Levy pattern, start exploring around it. In my experience, there are scores of places just as beautiful or as interesting right around the corner from the main tourist attraction that everyone seems to overlook.
When exploring a new city, I chart my route to include three to five major points of interest that are impossible to miss. This leaves me open to freely explore everything of interest in between so long as I’m generally going in the right direction.

Go at the Right Time

Above: Crowds photographing the sun rising over Angkor Wat.

A corollary for getting off the beaten path entails arriving at the less-trodden hour. I’ve seen vibrant local markets in the early morning transform into painfully tacky tourist traps after all of the locals have dispersed. Rainy season and winter deter many travelers, but oftentimes the rain is fairly predicable and more authentic experiences can be had in the colder months. For example, December is one of my favorite times to visit London because of the Christmas spirit, holiday parties, and few tourists roaming about the city.

As shown above, sometimes getting up early isn’t enough. While I took a couple obligatory shots of the sun starting to rise over Angkor Wat, I dipped out early to visit one of my favorite temple compounds nearby as the sun was still rising. I was able to get some very cool time alone at Ta Prohm while the crowds remained waiting for the perfect, but well-worn, picture of the sun rising over Angkor Wat.

Look Up, Look Down

Above: Looking up between business meetings in London.

It’s often disappointing to find beautiful, historical places you’ve envisioned from the postcard pictures ruined by lines of hawker stalls selling tourist trinkets. Just look right above (or below) the tourist bric-a-brac and McDonald’s and Starbucks chains to rediscover the real history.

Looking up reveals the timeless character of the place such as the ceilings of the Grand Bazaar in Istanbul and the beautiful traditional Asian architecture above street-level stores in Penang and Singapore.

Looking down often reveals similar discoveries, including the rich history of burial plaques on the floor of Westminster Abbey in London.

Stay Fit

Above: The conclusion of a road race at a Roman amphitheater in Amman, Jordan

Some of the best advice that I received before embarking on my extended travels was to take care of myself mentally, spiritually and physically. More than the mental and physical benefits, exercise while traveling creates connections and provides a unique glimpse into daily life.

Head out to your local gym (just follow the dated pictures of Arnold Schwarzenegger) to make new friends and experience some authentic local flair.
Create a social event by exercising with expats or locals. Lacking places to run in the hilly, non-runner friendly streets of Amman, I would regularly get together with friends to run laps up the largest set of stairs in our neighborhood followed by dinner together nearby.
Explore a new city by running to cover more ground and find interesting places to visit later. (Pro tip: Bring enough money for a cab ride home if you run too far.)

Go Deep

Above: One morning in Amman I walked into my local hummus joint to find my non-English speaking restaurant proprietor wearing a t-shirt from my alma mater.

While a whirlwind tour through as many countries and cites as possible is an absolute blast, it will feel incredibly trite after “going deep” and really spending time living in one place for several months.

Making lasting friendships, knowing the real local hangouts, participating in real cultural events such as weddings, funerals, religious holidays, even picking up some of the language are not possible with a fly-in, fly-out, see-do-conquer approach to travel.

Going deep also allows you to develop the small, but meaningful relationships in your daily life resulting in a much deeper, richer experience. Knowing your “chai guy,” returning to your local noodle shop where they already know your order, or trying to launch into a friendly, but often unsuccessful attempts at pleasantries with the non-English speaking doorman brightens your day and also keeps you from missing home when you’re away for extended periods of time.

Eat Everything, But…

Above: The result of my “point and see what you get” approach to ordering food in China.

As Anthony Bourdain often says, “Good food is all about risk… Food, for me, has always been an adventure.”

I agree 100%. You just want to make sure that you’re taking worthwhile risks. I’m typically game to try any street vendor, hawker stall or local restaurant, but here’s what I look for:

Is the place busy? If a lot of locals are eating the food, chances are so can you.
Is it recommended and/or frequented predominately by locals?
Does the food appear to be thoroughly cooked? Stay away from uncooked vegetables, particularly leafy greens.
Know when to avoid meat in certain high-risk countries. I often request to substitute a few hard-boiled eggs in place of meat.
Try Halal. More thorough cooking and, albeit marginally higher standard of care for Halal meat preparation, is comforting. This was particularly true for me when traveling in western China.

Don’t Go On the Cheap

Above: The Magelli Vila in Castel di Casio.

While traveling allows you to lower your cost base to pursue personal projects that may not be immediately financially viable, it doesn’t always make sense to choose the lowest cost options for lodging or means of travel. Here are reasons to upgrade, as least once in a while:

The people you meet. I try to stay in places that are nice enough that I’m meeting smart and interesting people, but not too nice where the atmosphere is stuffy or I’m hanging out with the retired couples by the pool.
Keep from getting burned out. I’m much less likely to get burned out on traveling when I’m staying at reasonably nice places. I don’t want to worry if my hotel will have a decent Internet connection or if my bathroom happens to back up to an open-air sewage ditch.
Seek rent parity. My approach is to focus on achieving “rent parity” such that I spend the equivalent amount on hotels over the course of the month as I would have spent on rent back home in Chicago.

Travel “On Set”

Above: The London “greasy spoon” featured in one of my favorite movies, Layer Cake.

Casting myself “on set” in my favorite movies or starring in my own Anthony Bourdain inspired travel food excursion is a fun way to structure my travel.

To locals, I might seem a bit peculiar in my excitement for a back alley in London featured in one of my favorite movies or the lengths that I go out of my way to eat at a dodgy Anthony Bourdain-featured food stand. But seeking out these types of places you often find interesting things along the way as well as develop a certain romanticized view and personal significance to the places that you’re visiting.

Keep Memories to Yourself

Above: Midnight reflections on a glacier-feed lake in Alaska.

You don’t have to document, post, tweet, share, snapchat, et la everything interesting and exciting during your travels. Keep some of these moments just for yourself.

I’ve also learned the hard way that a picture can never fully capture the moment or essence of the place. Just enjoy watching the sunset and don’t worry about adjusting the filter on your Instagram post.

Take Time For Sunrises and Sunsets

Above: The sunrise in Sabang on the island of Palawan in the Philippines.

The problem with sunrises are 1) they tend to be early 2) they are usually worth it. If I’m going to fly half way around the world, the least I can do is get up early a couple mornings to watch the sunrise or take a break early in the evening to watch a sunset. Doing so also helps me slow down and appreciate where I am.

Do Things That Give You Cultural Street Cred

Above: Enjoying durian while in Bali. Most durians are sold at roadside stands since the smell can be too strong to eat indoors.

I travel to better understand and connect with people. When spending time in a country, I try to find out what are people proud of and what local things I can do as sign of respect to those who live there.

From enjoying local music to eating at the local dive restaurants… anything that I can do to surprise my local friends and make then go, “What?! How do you know about that?” or “You’ve been where? I’ve never even heard of that city.”

Fasting during Ramadan will earn you major street cred in the Middle East. Or appreciating durian (above), one of the most controversial fruits with an extremely pungent smell, will impress locals in Indonesia and many other countries in Asia. Personally, I’m a big fan.

Eat With Locals

Above: Making toasts around the dinner table during Chinese New Years celebrations in the western Chinese Province of Shaanxi.

Some of the best advice that I received about understanding Chinese culture is that I needed spend as much time as possible around a dinner table with other Chinese people. While my Mandarin is effectively nonexistent, eating with locals was very rewarding and insightful into how local Chinese people interact with and show respect to each other.

I also had some very memorable meals eating with the people that I could hardly communicate with during Ramadan in the Middle East or with a nomadic family in northern Mongolia. I’ve found that others are often just as excited to host you as you are to join them for a meal.

Uniting people around the dinner table and the historic importance of breaking bread with people from different backgrounds are common threads anywhere that you travel.

Learn the Culture Through the Language

Above: Group of friends in after a wedding engagement ceremony on the outskirts of Amman, Jordan.

Not only does language open up many opportunities to connect with people, learning how people use expressions gives a unique insight into a culture. If you’re spending an extending period of time in one place, language tutors tend to be fairly inexpensive and also self-selects for interesting, outgoing people.

Use your tutor as a cultural guide as well as for your language learning. Many times language and culture are so intertwined that learning culture through the language will happen naturally.

Travel with People and Travel Alone

Above: Camping trip in rural Latvia near Ventspils

Both are fun and beneficial in their own ways. The most epic trips are always those that I share with family or good friends. But some of the most insightful times that I’ve had traveling I have been by myself.

When alone, I’m more likely to stumble into interesting, unexpected situations. There is also certain sense of freedom when traveling by myself.

Travel Planned and Unplanned

Above: Consulting our hand-drawn map while motorbiking in Myanmar.

It’s good to do both. It’s often hard to fathom traveling before the Internet and online travel bookings. Previously, traveling for extended periods required a much more improvisational approach compared to today.

While my personal proclivity is to plan everything with military-grade precision – from multiple maps of my destination, contact details, currency exchange rates, estimated ATM withdrawal amounts, etc. – it’s beneficial to sometimes to strike out without all of the logistics entirely known.

For me, there was a certain element of letting go in order to travel in an unplanned manner. But I found that you develop a certain confidence and feeling of freedom once you do.

Work On Something, Travel with a Purpose

Above: Attending a law school graduation ceremony in Zakroa, Jordan

For every leg of my travel, I try to have a goal or purpose. What do I want to get out of my time there? How do I want to be different when I leave? This ties travel together, giving purpose and greater context.

For me travel isn’t just visiting historical sites or sitting on the beach (though I enjoy doing that on occasion), it’s an opportunity to learn and pursue personal interests or passions. My goals might be to work on learning the language or better understand the culture of economically relevant places.

Stay In Touch

Above: Keeping in touch on a trip to the Baltics.

Take time to keep in touch with the people back home who mean the most to you. It’s ok if you want to have some space – after all, a big part of travel is meeting new people – but keeping in touch will keeps me from getting burned out on the road. (And keeps your family from worrying too much.)

Eat at McDonalds

Above: Sampling the exotic, local cuisine in Turkey.

While I love eating as local as possible, I always try to sample some of the “local” cuisine at McDonalds. In an attempt to cater to local tastes, you’ll often find rare and exotic dishes at McDonalds.

Some of my favorites include the McTurco in Turkey, the McArabia throughout the Middle East, the McProsperous in Indonesia, red bean flavored ice cream in China, and the “Surprise” sandwich in India.