When I was a kid I remember walking in Manhattan with my parents and brother and looking at how beautiful the buildings were. It was that same night that my mom said something I'll never forget: "Stop looking around like that or people are going to think you're a tourist!". Didn't even make sense to me. First off I was a kid and second I was born and raised in NY, why would people think I'm a tourist just because I'm enjoying the buildings? Ever since I have had a hard time participating in touristy things (thanks a lot mom!) as there is the underlined fear of crossing the thin line of city fun to full blown tourist.
I do have my regrets for letting this affect me. Had I have seen more sites when I still lived in New York I would've been able to enjoy the rooftops of the World Trade before September 11 occurred. Well you live and you learn, right? Now that I live in Chicago I want to appreciate and take advantage of the city it's landmarks, but how can I do so without looking like a damn tourist? Over the years I have devised some very helpful ways to work this out so whether you are visiting a new city or if you want to explore the one you live in, you can do so like a pro.
Do your homework.
Visit the city website or resource websites like Metromix, Yelp(or the Moms in the City calendar) and see what events will be taking place for you to take advantage of.
Travel in small groups.
There is no point in taking up the whole sidewalk, train car or bus with a huge group of people.. If you happen to be traveling with a lot of people it would be best if you travel in smaller groups so that you can have a more intimate experience. Try to travel in increments of 4 or 5 and for fun give each group a separate location to explore then share photos at the end of the night.
Don't carry maps!
Not only are they bulky but they are outdated! Depending on your cell phone you can easily access Google Maps and figure out anywhere you need to go at the push of a few buttons. Leave the maps at the gas station.
Visit tourist attractions on weekdays.
By visiting attractions during the weekday you won't not be overrun by mobs of people and there are usually great deals such as half price off fares during the week.
Visit local staples.
Everyone knows of and has visited famous skyscrapers and restaurants but there are many local venues that are unique and that would be worth checking out. Try visiting local coffee shops, hole in the wall restaurants and independent clothing stores. You are almost guaranteed not to find a duplicate any where else!
Go to bars and hot spots on non-busy days.
City bars and clubs are always busy on the weekends but generally are a low-key hangout spot on days like Tuesdays or Wednesdays. By visiting a bar on a slow day you can not only almost guarantee that you will get a place to sit but you won't have to scream or yell to have conversations.
Take advantage of free city events. One of the best concerts I've ever seen was at the Taste of Chicago and I got to watch Stevie Wonder play for three hours...for free! There are many events that cities host for free such as music concerts, movies in the park, free days at the museum to street fests. Of course this works well with the first trick of doing your homework to see what events will be taking place on the days that you want to hit the town.
Join Meetup Groups.
Not only can you join groups on Meetup for free but you can get to know moms from any different areas and they all just want to get out of the house and have a good time too. If there is a place that you've always wanted to check out but can't get one of your friends to go with you can list it as an "Idea" on the groups site. There is bound to be a mom or two in the group who will tag along. And if you can't find someone from one group, join another! The best part about it is that you have options and what girl doesn't love variety??
