My friend Elizabeth and I have boys that are exactly the same age and who have similar temperaments and interests, but they don't get to see each other a ton because we live in Evanston and they live in St. Louis. They have come to Chicago a few times because they have family here but we haven't gotten out to St. Louis mostly because I'm just not up for doing a longer overnight trip with both of my kids yet (because I am a wimp).
However, Elizabeth and I recently realized that if we just took our older kids (and left our toddlers behind) we could meet up between our two towns and actually get the chance to talk and hang out, which hasn't been super feasible to do with kids up until this point. Some kid or another required close watching, but we finally reached a nice milestone where we could see each other and the big kids could prett much entertain themselves.
So Saturday we booked two rooms at the Hampton Inn in Springfield, which is sort of between St. Louis and Chicago. We were pleased with how this trip turned out. We had really low expectations in terms of actually doing stuff (people kept telling us cool things to do in Springfield, which we will maybe do some other time.) Instead, we chose a hotel with a pool and brought the boys' floaties in addition to some pool toys (including three identical Spider-Man toys). We also packed three bottles of wine (and requested a fridge for our room). Saturday afternoon kids swam and played in the pool for two hours while Elizabeth and I had cocktails and caught up. The boys were at the perfect age for this type of thing--old enough to play in the pool but young enough to wear the floaties which meant we could let down our (life)guards a little.
Christopher has food allergies that makes depending on restaurant food a chancey endeavor, so Elizabeth packed a toaster and food for the boys (otherwise if you did this trip you could just go out, or order a pizza, or bring PBJ, even.) After taking baths, the boys snuggled in bed and watched Trolls on an iPad while eating dinner (spoiled.)
Meanwhile, I had brought some cheese, crackers, sausage, dips and cookies, which we enjoyed while sporadically going to the adjoining room to yell at the boys. We thought that they'd be pooped from their time swimming, but, no, they had discovered tandem bed-jumping. The nice thing though was that while it would have been ideal for the little angels to fall asleep by 8, the stakes were low. We had nothing planned in particular for the next day. I think we just yelled at them because that's the circle of life. One day your parents are yelling at you not to make another peep and then suddenly that's you doing the yelling.
The boys finally fell asleep around 10:30 and were up at 7. I dumped some toys in their room to keep them occupied while Elizabeth and I took our time getting up. We then availed ourselves of the Hampton Inn breakfast buffet and it was back to the pool, which was also being utilized by about a half dozen girls from a high school basketball tournament, so the boys were intrigued by them but tried not to show it.
Finally it was time to shove off. Elizabeth and I agreed that a Midwest car trip is not complete without a trip to Culver's, so we drove 15 minutes to meet at one. On the way Paul said, "I miss Christopher." Because he was being a good guy, I let him get a milkshake although he fell asleep--for over two hours!--in the car on the way home after having drank just a bit of it.
In the end I think Paul and I spent over six hours in the car together and I was pleased that aside from a five minute interlude when I had to run back into the hotel to retrieve a forgotten Spider-Man and needed Paul to just stay in the car for a second and let him play Duck Duck Moose on my phone, he managed to get through the car trip screen-free. This was thanks to Jonathan Messinger's wonderful kids' podcast The Alien Adventures of Finn Caspian. Paul is four and a half and I think just old enough to get it and pay attention so if you have a kid of similar age, definitely give it a try.
So that's it--it's not exactly Disney World, but it wasn't our basement, either. If you and a friend have kids who get along and are mature enough to handle a sleepover, it was a great time--easier than a whole family sleepover and more fun than a typical weekend at home.