Last time we took a \u201creal\u201d vacation of any kind was to visit Chicago. That way was almost exactly two years ago, and I was hugely pregnant. I remember standing on a street corner near the Chicago River and saying to Bryan, \u201cNext time we come, I\u2019ll probably be pushing a stroller.\u201d I was right. Last weekend, we decided to pack our kid in the car and attempt our first family road trip. When we found out my old college roommate would be in Chicago for a conference and staying with some other college friends, we knew we had to be there. To say this trip was different would be an understatement. There were no late nights out and I didn\u2019t manage to do an ounce of shopping, even after breaking my sunglasses and cutting my face with them. Instead, we pushed the stroller \u2013 for the first time all summer, actually \u2013 up and down the city\u2019s streets as we trekked from our apartment (more on that in a moment) to our friends\u2019 apartment and to lots of parks and attractions in between. All the memory-making aside, there was a lot of lesson-learning for us still-floundering new parents. (Are we still \u2018new\u2019 at this two years in?) Here\u2019s what we know now that we didn\u2019t know before. Pack lots of animal toys. \u2013 Olivia has one favorite stuffed animal she carts around pretty often. But even he couldn\u2019t entertain her when the car ride seemed to be taking forever. Sitting in the back seat with her, I busted out the little plastic horses and we crashed them and made them run and talk. It staved off the crying for a little while. Get a place with a kitchen and a bedroom. Stay out of restaurants. \u2013 This is a big one when your kid is still small, as we\u2019ve found when we\u2019ve taken other smaller trips with our baby. It\u2019s nice to have a place to store some milk and to have a door to shut between you and the napping child. We booked an entire studio apartment through AirBNB.com, which saved us a lot of money and gave us a homier place to come back to at the end of a long day. We ended up cooking at our friends\u2019 apartment, but if we hadn\u2019t been visiting them, we probably would have cooked all our dinners \u201cat home.\u201d Restaurants, like backseats, aren\u2019t exactly conducive to toddler behavior. Scale back. \u2013 There\u2019s a real temptation to do and see everything when you travel, but kids don\u2019t have the tolerance for everything. So you have to do less each day if you want to enjoy anything without an exhausted, cranky kid. We kept our plans flexible, did less and spent more time just hanging out at parks than we normally might have, but it kept our kid happy and gave us a chance to chat with our friends while she played. Stay longer. \u2013 Yes, stay longer. This helps with scaling back because you feel less pressure to pack more activities into each day. You won\u2019t feel rushed or stressed and you won\u2019t push your kids too far. It also gives you a chance to establish something resembling a routine. Did we do it exactly right? I don\u2019t know, but it worked. We all came home exhausted, but renewed in a way that only comes after a change in scenery and a reunion with people you love. We\u2019re already planning our next adventure. Whitney is the Pioneer\u2019s parenting columnist. After four years reporting and editing at the paper, she\u2019s stepped back to spend more time with her family. Read more here each week and reach her at firstname.lastname@example.org.