10 Ways to See and Experience More When Traveling

10 Ways to See and Experience More When Traveling_Sidewalk Blog

There is something magical when we visit a new place, whether it is a new country or just a different part of the neighborhood. Novel places offer an opportunity to get out of our comfort zone, to push on our interpretations of the world, to empathize, and perhaps even to come back home with a good story or two. But these experiences do not just happen to us; we have to pursue them.

Over the course of a recent conversation, a friend and I started discussing advice for how to experience more when traveling. We ended up cobbling together a list of ten rules to explore deeper. This isn’t a checklist of things to do before going (such as photocopy/digitize your passport, use ATMs rather than traveler’s checks, etc.) but suggestions to get more out of your experience.

Take a look and share your thoughts in the comments section on what additions or changes you would suggest.

1. Become Curious

The best experiences begin as soon as we adopt the following mindset: everything is a cultural experience worth absorbing. The sooner we buy in, the sooner we can be awestruck and bewildered about what’s new around us.

This ethos also allows us to better navigate cultural differences and unforeseen circumstances. Rather than fume about the 14-hour delayed train, just ask, “I wonder why that is, and how does that impact everyday people?” Rather than gripe about a local delicacy, think, “Isn’t it interesting that this came to be?”

2. See the Big and the Small

When in Rome for the first time, you kind of have to see the Pantheon, Forum and Colosseum. But there is a lot more to Rome (and anywhere else you go) than just the main attractions. Just for the record, Giolitti - one of the best gelato shops in the world - stands just four blocks from the Pantheon.

A few tips on how to notice the small details

  • Take a new path. Try not to walk the same street twice. If you have no choice, be on the lookout for something new.

  • Look up. I say this only semi-sarcastically: there is usually decent architecture and ornamentation above street level.

  • Explore beyond the attraction. When at big sites, give yourself some buffer time to explore a few blocks around the outskirts. There is often authentic everyday life happening just steps away from tourist attractions.

  • Get lost and wander. Novelist Lawrence Block explains, “our happiest moments as tourists always seem to come when we stumble upon one thing while in pursuit of something else.” So much can surface when we aren't looking for it. Before setting off, it may be a good idea to study a map for key landmarks and keep an address for home in the back pocket.

3. Go on Foot

In general, cities are best seen on foot. There is no better way to witness the culture, sniff the smells, peruse local livelihoods or learn about a place than by rubbing shoulders with the locals on the sidewalk. The act of walking forces us to slow down and observe. Walking allows us to steal a second glance. And a third if we want.

Exploring a city on foot also allows us to appreciate how a city was designed and in what era. The cobblestones of Barcelona tell a different story than the boulevards of Beijing and the grids of Chicago.

4. Get Friendly with the Natives

The goal is to see the hidden gems and local specialties. The locals have the knowledge and access. It’s a good idea to step away from the guidebooks and head to the local restaurants and bars.

I try to strike up a friendly conversation with a waiter, bartender or resident sitting nearby. After establishing a solid foundation of common ground interests, go in for the ask. You never know what opportunity will present itself, but it will likely be something few others experience.

Good questions to lead with:

  • What neighborhood/place/experience is overlooked by visitors but should definitely be seen?

  • If you only had one last day in this town, what would you make sure to do?

  • What are your favorite restaurants/cafes/stores/streets in town? Why?

5. Find Opportunities for Excellent Photos

Play a game when traveling: the photographer of the day's best picture gets a prize. Something changes when we put pressure on ourselves to take photos: we become more observant, patient and adventurous. We seek for angles and crowds. Whether we take a photo or not, we thrust ourselves into situations to have memorable experiences.

To encourage this habit, take your camera out of your backpack or pocket, wrap the strap around your wrist for security, and head out. The best camera is the one you have with you, whether it is a DSLR, a smartphone or a disposable point & click.

6. Study the Ordinary

So often we make travel about hitting a number of points of interest and checking boxes off lists. As great as it is to see the Louvre, Notre Dame and the Arc de Triomphe, they do not represent everyday Parisian life. The first step in understanding a new culture is observing it.

Take a moment every day to witness daily life. Ten minutes of sitting in a park or near a busy street corner is all it takes. Here is an exercise to take in the surroundings:

  • Minutes 0 - 3: Watch the comings and goings. Where are people going? What pace? How are they dressed and what are they carrying?

  • Minutes 4 - 7: Listen to the sounds of the environment. If it helps, close your eyes. Do you hear people? Machinery? Natural sounds? Music?

  • Minutes 8 - 10: Note the smells nearby. Are there traces of dust? Grass clippings? Chemicals? Salt water? Buttery pastries?

7. Know What to Plan and What Not Plan

“A good traveler has no fixed plans, and is not intent on arriving," philosophized Lao Tzu, the author of the Tao de Ching. There are some limits to this, but it is good to maintain some room for spontaneity and serendipity. If you plan an entire adventure, you leave no room for the actual adventuring.

Schedule the following:

  • Air transportation - just about everything other than flights can be accomplished 24-48 hours in advance.
  • Lodging - usually wise to schedule in advance, however you can get away with just showing up and seeing what's available in Europe. Services like HotelTonight is great for last-minute lodging in the US.
  • Hugely popular exhibits or timed events - be sure to investigate advanced purchases for museum exhibits, live performances, popular restaurants and restricted parks like Yellowstone.

Just about everything else can be done on the fly.

8. Bring a Passion or Hobby from Home

One of the most rewarding things to do in a new place is to observe the local interpretation of something we do at home. As a Boston Red Sox fan, one of my favorite memories in Osaka was cheering in the die-hard fan section of a Hanshin Tigers baseball game. The Japanese flavor of baseball and fan involvement is completely different from American customs.

If you love cooking, take a spring roll-making class in Hanoi. If you are big into live rock music, catch a concert at The Cavern Club in Liverpool (where the Beatles honed their sound). Seeing how other cultures perform a custom can only lead to further appreciation of both.

9. Take Local Transit

This suggestion is a little more tactical than the others: local trains, trolleys and buses provide better exposure to a culture than private transport. Local transit is a fountain of rewarding stories, civic rituals and opportunities to engage with the natives. In addition, it is usually the most economic way to uncover cultural experiences.

10. Seek Adventure

If you could internalize only one thing from this post, it would be this: Say yes.

The best travel stories never came from saying no all the time. To quote Mark Twain, “Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do.” 

Of course, don’t be an idiot and don’t be a statistic. But, also don’t treat a day in a new place like a typical day at home; it’s not often we get a chance to see a place with a fresh pair of eyes. Might as well do it right.

Jason Donahue_Co-Founder & CEO of Sidewalk

Author: Jason Donahue, Co-Founder & CEO  

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