How To Be A City Guide That Will Blow Your Visitor’s Mind

Whenever friends of mine decide to come visit me in Chicago, my reaction is always the same: excitement, followed immediately by terror. My head begins to spin with all of the things we have to do, and how little time we have to eat it all – deep dish, hot dogs, Italian beef, good lord we’re going to need Tums. It’s extremely difficult strike the perfect balance when it comes to planning: to plan enough that you don’t run out of things to do, but not so much that everyone is exhausted after day two. When it comes to taking on the role of unofficial city-guide, it helps to have a few tricks of the trade. With this five-step guide, you can actually enjoy your friends being in town, and avoid running around clutching a whistle and a bus pass trying to get everything done. Here are five simple rules to ensure your visitors, and you, have a great time on your home turf.

1. Get the touristy stuff done on the first day.

Screen Shot 2016-03-03 at 1.29.04 PM

This is crucial. You don’t want your guests worrying the whole trip that you’ll never make it to the attraction-your-city-is-known-for. Make your first day a wham bam thank you ma’am of downtown tourist attractions. The best part about these attractions is they usually they don’t take very long for out-of-towners to see and be done with, so if you can knock all the photo-ops out at once, you are instantly hailed as a 5-star tour guide and free to show your visitors the real gems for the rest of the trip.

2. Consider your stamina.

Screen Shot 2016-03-03 at 1.28.25 PM

Think of the first day as a trial run – did you come home exhausted and ready to starfish on the carpet, or was your friend looking like a caged animal the second you walked in the door? Don’t force an all-over-town itinerary on someone who would rather veg out and catch up, and if the energizer bunny has come to stay, plan accordingly. Additionally, if someone is staying with you for longer than a weekend, they’re probably going to need a rest day with some alone time. Providing them the time to rejuvenate and recover will make the rest of the trip even better.

3. Know your visitors.

Screen Shot 2016-03-03 at 1.44.53 PM

If your visitor is a sports fan, score cheap tickets and take them to see your favorite team. If they’re into music, see if any of your favorite artists are in town or troll for a free concert. It is also always helpful to ask visitors ahead of time if there is anything in particular they would like to see or experience while in town. That way, you can have one event planned in advance that everyone (including you) can get excited about.

4. Hit a few local-flavor highlights.

Screen Shot 2016-03-03 at 1.33.55 PM

You want your friends to leave ranting and raving about your home city? Baby, you’ve got to feed them. I usually plan for two epic mealtimes, one low-key local favorite, and one more experiential dining experience. When choosing your must-eats, trust your instincts. If you believe deep in your soul that the hole in the wall with hand written signs in the windows is the place to be, take them there! Balance out your secret spot with a restaurant they recognize, or that feels right for an extended dinner and some celebratory drinks.

5. Make their priorities, your priorities.

Screen Shot 2016-03-03 at 1.42.40 PM

If your visitors want to score some city-garb, make sure to hit up some stores and get them their souvenir fit. Ask them near the end of the trip (when there is still time) if there is anything they wanted to do that you haven’t done yet, and do your best to make it happen. The fact that you care will mean a lot to them, and if you can send your visitors home feeling that they’ve done everything they hoped to and more, you’ve surely earned nailed your role as city-guide square on the head.

Originally Published on

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s