Jack and I arrived in Honolulu (the winning destination of WanderTot’s poll) tonight after Jack’s longest flight yet. I still can’t believe he stayed awake for the ENTIRE seven-and-a-half-hour flight.

We were scheduled to arrive yesterday, but our flight left without us even though there were 11 empty seats, thanks to weather-related weight restrictions. I was like, come on people, you can let on the skinny chick and the baby!! No such luck. Thank goodness we got on today and, not only that, we got an entire middle row of three seats to ourselves.

Everything was going great until, an hour into the flight, the top popped off Jack’s sippy cup, which was FULL of apple juice. It spilled all over him, so he was soaking wet from neck to toe, I mean DRIPPING wet and screaming because a) he had no idea what just happened and it terrified him and b) he was cold and wet. I took off his shoes and braces to make it easier to change his clothes in the cramped airplane bathroom. BAD IDEA. He stood on the floor while I took off his pants and diaper. The second I took off his diaper, he peed. Did I mention I left his socks on? Yep. I brought a clean shirt and clean pants, but I did not foresee him peeing on his socks.

Yeah. So. I just let him go barefoot while the socks were drying out. We went for a much-needed stroll around the plane and I definitely got some looks. The where-are-that-poor-baby’s-shoes looks. Eventually, I had to put them back on because Jack has to wear braces on his feet and he can’t wear the braces without the socks. Also, pee is sterile so don’t give me that look.

So then, THEN, we had another little incident, which you may not care to read about if you don’t yet have children. Let’s just say some of the airplane food didn’t agree with Jack and we had a leaky diaper situation. I had only brought the one extra pair of pants onboard and now they were ruined too. I had two choices. Let Jack rock the diaper, shoes and shirt look or put back on the apple-juice pants. Luckily, they had had about four hours to dry out, so they were only damp when I put them back on. Now the only clean thing the poor kid was wearing was his shirt.

Lesson learned: bring one change of clothes for every few hours on a flight. Plus extra socks.

The rest of the flight actually went really well and Jack was pretty much an angel aside from the forgetting-to take-a-nap thing. He ALMOST fell asleep after we touched down, while taxiing to the gate. He completely conked out on the shuttle ride to the hotel.

I hope he can sleep on the plane on the way home. Especially since it’s an overnight flight.

Now that many airlines are charging per bag you check in, including the first bag, it matters more than ever that you pack smart. Even if you can bring more bags without the extra charge, it’s still another piece of luggage you have to lug from your car to check in and then again from baggage claim to your hotel. Plus, if you can manage to get everything in your carry-on, you can skip baggage claim altogether.

I find I can travel with my toddler for up to a week with no more than a carry-on bag, a diaper bag and an umbrella stroller. We parents are lucky in that we can usually bring a carseat, diaper bag and a stroller for free and none count towards our allotment of luggage. I was very surprised (and thankful!) to learn that the first time I flew with my baby. Still, packing all we need in one suitcase and one diaper bag is quite a challenge.

The most helpful technique I know is to roll your clothes instead of folding them. Not only does this save space, it also helps keep wrinkles at bay. Try it and see what I mean. We are able to bring about three outfits a day for Jack (one for each meal) and a few extras for me this way.

Make the most of your diaper bag. Even if you are carrying on another bag, try to keep everything you’ll need to access during the flight in the diaper bag. Trying to get something out of a second bag mid-flight is just way too much of a headache.

Our diaper bag packing list:

• iPhone
• Wallet
• Boarding passes
• Two stackable sippy cups (one for me and one for Jack—if I want to get a drink on the plane, I pour it in the sippy cup so Jack can’t spill it)
• Snacks (including a lollypop for emergency use only)
• Easy-to-rinse bib
• Enough nighttime diapers (why nighttime?) to last until we get to the hotel
• Travel-sized package of wipes
• Shorts for Jack in case his pants get wet or dirty
• Several small toys
• Three or four small board books
• Jack’s lovey

All of the non-toy items also do double duty as toys. My wallet or iPhone will entertain Jack for longer than any of the actual toys.

You also want to be as smart as you can about packing your suitcase. When deciding what clothing to bring, try to consider what will take up the least space. Do you really need a thick sweatshirt or will a thin sweater do? Consider packing dresses (unless, of course, you’re a guy who’s not into that sort of thing). Dresses give you a whole outfit for practically no space at all. If you’re really tight on space, you can stuff your socks into your shoes to make the most of space that would otherwise be empty. Also be sure to make the most of any outer pockets on your bag. I usually stuff as many diapers as I can in those.

Our carry-on suitcase packing list:

• Clothes
• More nighttime diapers, plus regular diapers and swim diapers
• Package of wipes
• More stackable sippy cups
• Laptop
• Camera
• Ziplock bag of toiletries, including travel-sized baby sunscreen and baby Tylenol
• Comfortable walking shoes
• Flip-flops
• Sunglasses
• Baggallini Bag in a Pouch

Be sure to keep anything you need to take out at the security checkpoint easily accessible, which in our case includes the laptop and ziplock baggie of liquids.

It is also important to pay close attention to what you wear on the plane, as that’s part of what you’re bringing with you. I wear black pants, a patterned dark shirt and black slip-on shoes. The slip-on shoes are a given; it is hard enough to get through security with kids in tow without having to tie and untie or buckle and unbuckle your shoes. The black patterned shirt and black pants look nice, which puts passengers around us at ease (the frazzled-mom look is not too comforting in a row-mate), but more importantly, it is pretty darn good at hiding anything Jack decides to spill/wipe/etc. on my clothing. If you have a young baby, I would recommend adding a shirt underneath in case you need to take off the top layer due to a bad spit-up incident or leaky diaper.

Jack’s airport outfit is similar to mine: dark pants and a T-shirt under a patterned button-up shirt. I like to put layers on him so I can take one off if he gets warm and put it back on if he gets cold. Plus, that’s more clothing we have with us without taking up space in our luggage.

Consider your options carefully before giving up and adding another bag to the mix. Can you purchase diapers at your destination? Can you do a load of laundry at the hotel? Do you need your shampoo or can you use the bottle the hotel provides? Is it really worth the money to pay to check the suitcase there and back and have the hassle of another bag or can you do without some of the stuff?

Even if you do end up bringing another suitcase, hopefully these tips will still help you make the most of it!