5 Tips For Reintroducing Yourself to Big Cities and Urban Environments

Reopening is happening! You are eager to travel again (YAY!) Does the thought of visiting a big city and the urban environment give you a bit of anxiety? Maybe before COVID, you felt a bit intimidated by the sounds and tall buildings but comfortable sticking to the tourist maps…and now? Now, the thought of crowds and touching things lots of people touch and being close to others and…well, you get the idea. 

I am based in Chicago, Illinois, in the U.S., and provide urban photography tours to people from around the world who live in a variety of environments. As a “big city girl” who lives IN a large metropolis, I understand your concerns and fears. Believe me, after 2020, even I had to reintroduce myself to my city! As a tour guide, I try never to assume my clients are from or comfortable with a big city. And then COVID hit. Chicago turned into an empty big city ever so slowly awakening, and I found I had to go through the motions myself. It’s that whole ‘oxygen mask’ scenario – I have to put mine on before I’m any good helping you with yours, and here we go!

Here are my FIVE (5) suggestions for reintroducing yourself to urban environments:

1. PLAN AHEAD – ish

Plan the major things – transportation, lodging, a couple of tours and dining options – and allow breathing room for serendipity, curiosity, opportunity, weather or delays. As businesses reopen, they may be trying new things, new schedules, ever-changing restrictions or precautions.

Sidebar: PLEASE be kind to those providing services to and for you, from the most obvious to the “invisible”

Finding a mix of ‘planned’ and ‘opportunity’ might give you some comfort knowing you’ve actually allotted for that “thing” that happens and you’ll better enjoy your visit.


Yes, I said it! Who better than a local to help you? My arguments:

  • We have a passion for our city we enjoy injecting into others (sorry, couldn’t resist the bad but more positive vax pun)
  • We know tourist hotspots AND local gems
  • We know the best way to navigate the city – where to go and not to go and how to get there
  • We know both the high-end and budget-friendly options. It’s no secret big cities can be intimidating and, if you want to try public transit, a roadmap without a compass
  • We are like a hotel concierge but haven’t been paid or schmoozed to promote places and things to do
  • And if a photographer, we know the best places for photos and the best time of light to be there!

If you assume it’s too expensive, consider the costs of getting lost, losing time and paying too much because you’re a tourist. While you often do get what you pay for, there are options from free (with gratuity) to bespoke in many places today.

Bonus: Hiring a local is also supporting and shopping local!


You know your needs best. Is there something you can pack that will provide you a bit of familiarity, comfort, peace? Is it earplugs because the city sounds are too much for you? Is it a music mix to listen to while you explore, take a break or to fall asleep to? Is it something you’d rather not spend exploring time shopping for? Is it a favorite snack you’re unsure you’ll find in your destination (of course, first check your transportation and destination country’s guidelines). Afraid you’ll overpack? Allow yourself this once, if for no other reason than to lessen some anxiety.
Rule of thumb: Don’t pack anything unlikely to be used or you’ll spend the entire trip worrying about (camera gear might be an exception, but I’m biased)


If this is your first immersion in an urban environment since the beginning of the pandemic, even if it’s your own local city, start slow! Don’t pack your schedule so tight, you risk feeling physically and mentally exhausted or overwhelmed. You don’t want the result to be bad memories and the lack of desire to go again. I want you to enjoy this!

When you arrive in your destination city and are settled with your accommodations and all, I highly suggest you go outside and just stop. Spend a mere few minutes engaging your senses and becoming familiar with this environment:

  • Look around at the buildings, the people, the modes of transportation (maybe boats, trains, trolley, pedicab, whatever), food carts or trucks, tourists vs locals
  • Listen to the sounds around you – sounds of conversations, horns honking, steel rubbing train wheels, splashing of water, the wind
  • Smell the city. Ok, not ALL smells are good and you may smell what I call that “urban smell”, but it’s engaging your sense of smell nonetheless. Food being piped from a restaurant, the sometimes fishy smell from water, perfume or cologne of a passerby

When you’re ready to begin your activities, take only the essentials you need while out. You’re not going to be comfortable loaded down and feeling the need to guard everything. Take a little more time than you might normally to observe, learn and experience each thing. 

It’s always, always, always a good idea to be aware, perceptive, observant. This is common traveler advice I see many not follow. Cities have more people but, in my opinion, are really not much more risk when it comes to being unfamiliar and having people who can take advantage of you. If it’s an unfamiliar place, it’s easy to become distracted or confused. Positioning yourself and your belongings in a way that allows you to remain aware is important. If you set anything down, keep physical contact with it (set it on your foot, for example) rather than turning your back or stepping away. This is just one example of ‘what not to do’ and the MOST common mistake I see visitors make and it doesn’t matter if you’re a solo traveler or in a pack.



No, really, breeeaaattthhheeee. Let’s face it, we’re out of practice with crowds. If there are too many people around, breathe. All the sounds are returning. If it’s too noisy, close your eyes and breathe. If you’ve walked too much, step over to the side, find a spot to rest and breathe. It’s a lot, I know. You’re doing great!

Are you feeling a bit of anticipation anxiety about this trip or being in the city again? Grounding techniques are a tool people who experience anxiety and panic attacks often use and they’re just as good for you in this situation…and even before. Think like someone tapping you out of a fixated thought or taking control of your body’s ‘fight or flight’ response. I’m still working on my go-to set of things to do and have found this process incredibly helpful. I’m not a psychologist so I can’t suggest specific things for you, but speaking with a professional (it’s the hip thing to do after all we’ve been through!) or a quick internet search will give you some suggestions.

Trust yourself, allow yourself a bit of grace and, most importantly, enjoy, enjoy, ENJOY is your goal!

I hope you find this article helpful. If you try any of these tips and find them helpful, please let me know what worked for you.


Did you know I’m an affiliate marketer for two great photography products?

CreativeLive to kickstart your learning, teach you something new or download John Greengo’s Fast Start of the new camera you got. Clicking on this link will allow them to share some of your purchase pennies with me for telling you about them.

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