In one of Thatdad's books, he began a chapter describing the different approaches Thatbrother and I take to planning trips. Thatbrother flies by the seat of his pants, barely reserving a plane ticket before heading out. I plan everything down almost to the minute - tickets, reservations for hotels and dinners, maps between activities.
Traveling with an infant is a whole 'nother ball game. As prepared as I normally am, I still felt wholly unprepared. So you can learn from my mistakes. Here's how NOT to travel with a baby.
1) Don't slack off on research. Maybe this just pertains to me. As I mentioned, I usually have a mini-binder for each trip with all our reservations printed out, maps of the area, etc. But normally I also have time to do this. Now that Thatbaby is with us, I have far less time for planning. So I let this slip. And paid for it. Like when I thought our dinner reservations were in one area of town, and they were miles away in another part of town and I had to figure out how to get there, in the rain, and we were horribly late after getting lost.
2) Don't overplan. When Thatboy and I travel we usually fill our days. We leave the hotel early and don't return till late at night. This does not work so well when traveling with a little guy. Next trip I'm definitely keeping it simple and only planning one activity a day, with time to come back to the room and just relax instead of rushing from one thing to another. No horror stories about this one, it worked out all right (Thatbaby will sleep anywhere and just took his naps in the carrier or stroller), but we were exhausted every night. Not a very restful trip.
3) Don't assume the weather will cooperate. Our trip was to Chicago. In August. Knowing this, I removed Thatbaby's sweatshirt from my diaper bag before we left. Thatboy and I decided we didn't need to pack any long pants or shirts for him or us. So of course, one day it rained from dawn till dusk. And this happened to be the day we planned on walking around town. And the day we got stuck in outdoor lines for every activity we had planned. It was pretty miserable for everyone involved.
4) Don't bother bringing any reading material for yourself. There won't be time.
5) Save some activities for when they're older. Thatbaby did not enjoy the architectural boat tour and therefore we did not enjoy the architectural boat tour. He wanted to crawl around and be crazy, not listen to the docent and enjoy the boat ride. In retrospect I wish we had waited on this one.
And things we did right:
1) Get bags for your stroller and carseat. We just got some cheap ones, but they made things so much easier. We could shove extra things in the bags because they were so big. The carseat bag had backpack straps so Thatboy could wear it through the airport, leaving his hands free to carry our carry-on.
2) The babycarrier is THE way to go. We got a lot of recommendations to stroller through the airport, but putting the baby in and out of the stroller and folding the stroller up is a big PITA. We opted to check our stroller and then wear Thatbaby through the airport. This means I didn't even have to take him off through security. It also made him so easy to get on and off the plane.
3) Make little "packs" for the plane. We put our carry-on up above and had little gallon ziplock packs under the seat. There was the "diaper" pack with some diapers and wipes for quick diaper changes. The "toy" pack with new toys for Thatbaby (a Sqwish, an O-ball, and a new cloth book - the magnadoodle was up above in the big carryon). And there was a "snack" pack with blueberries and dried raspberries.
4) Go with the flow when it comes to sleep. I think Thatbaby was in bed by his "bedtime" once during the trip. Usually he ended up going to sleep a little later, but it's a vacation, so I wasn't going to worry about it. We brought the pack 'n play from home, and he slept there most of the night, but in the early mornings he ended up in bed with us so we could sleep a bit longer. He loved the big fluffy bed and spent a lot of time throwing himself down on it over and over again.
5) Pick up some stuff once you get there. We brought a handful of diapers and picked up the rest once we got there. That way you don't have to pack mountains of diapers and wipers. Once we checked into the hotel we made a diaper-wipe-dishwashing soap run.
6) Use the day you get to get oriented. This is time for the diaper run, finding the nearest supermarket, subway stop, restaurants, places to get drinks. Even though I overplan, I did this right. Our first day in was also our most relaxing. And it meant I knew where to pick up things when we ran out, where we could find buses and the metro, and get a lay of the land.