Okay, traveling with the boys. I have gone through many phases and issues with traveling since Travis was born. I found the first picture of traveling with Travis:
We went to Wisconsin to see my family since Randy left for a work conference. This was before the days of no liquids and shoe searches. I schlepped everything with me for the week trip. When I traveled with only Travis I never checked anything. I could fit all of our clothes in my rollaboard and then I attached his car seat to the suitcase and then the backpack and baby/boy as you see in the picture. Things are a little different now, but I'll tell you what process I use for traveling with the boys.
My travel theory: If I want to have it, I should bring it. Don't expect the airline to care for my children. If I bring it, I should be able to transport it (lift and move). I don't use electric carts in the terminal.
Packing:
I have spread sheets called "Traveling with Travis" and "Traveling with Justin". Everything I need to take is divided into categories: Clothing, Toiletries, Eating, Toys, and Miscellaneous. What is in each of those categories changes based on age of course. But I list everything that I need to take, from pants and underwear, to a sippie cup and trucks. And I mark which things are liquid, just in case I decide to bring it on the airplane. I can check things off as they are gathered and I can take the list with me for gathering items on the other end. It has helped me many times not to forget a nightlight we have brought! If you want copies of these, I can e-mail them to you.
Now I use a large suitcase for all three of us. I use only one bag so I only have to pull/manage one bag. I pack the clothes in outfits for ease in dressing in the morning. I try to put the boys in matching clothes for the flights to and from so if I lose one I can say, "He looks like this!" and point to the other one. (Even if it's just blue shirts and jeans!) I always take diapers with me because then as they are used I will have the extra space for the return. It may just be me, but things never fit in the same coming home, and I always bring home more than I take. Maybe it's just our family. And I take a small duffel bag in case we acquire more than I planned!
Then for the plane we take a backpack, the one in the picture. It is great! It has two small zipper pockets for cell phone, camera, keys, wallet, and kleenex. (I always travel with kleenex, even if no one is sick!) Then the larger compartments fit, from small to big: 1- changing pad, diapers (4-6) and wipes (lots, in a plastic bag), 2- toys for Justin, 3- a change of clothes for each of the boys, from underwear and socks to pants and shirts, DVD player with headphones (airline rules require headphones) with the charger, and lunch bag.
Travis has his own backpack that has his sippie cup (empty- filled after security) and toys for the trip. I let him take whatever he wants, but just make sure it's not too heavy because I don;t want to end up with it! I think a backpack is better for Travis because he runs and jumps and needs both of his hands. I would end up his rolling bag if that's what he used.
The lunch bag has yogurt for Justin (tubes) and grilled cheese sandwiches. We always travel with grilled cheese. Security can be picky about peanut butter and jelly sometimes, but if you put it in your "liquid" bag it would be fine I think. And mayo scares me. For us, grilled cheese works the best. I have never had a problem with an ice pack, but we have always had a baby so that might be it. If they want to take the ice pack, I would let them. I have 2 quart sized plastic ziplock bags that I could take to a food vendor to fill with ice (and then double bag for leaks). I also travel with plenty of non-refrigerated, non-crushable snacks like dried fruit and granola bars. I also have a bib and Justin's cups. This past trip I put all of the baby spoons in the checked bag accidentally and so when I fed Justin his yogurt I had to use a stir stick from the airline. The back end worked just fine for our purposes because it was thick. I carry a disposable water bottle that I pour out and then refill after security. I am into minimalism so when it's empty it can crush slightly and then it doesn't take up so much space! On the airplane I request water with no ice and then pour it into the bottle. My first 2 flights with Justin I ended up with wet crotches when he tipped the drink all over me. Water is the safest and least staining liquid.
Traveling:
I do not take a stroller unless I know I will need it for something on the other end for something other than through the airport. They require both hands and they do not carry both car seats well. It's just extra for me. Car seats are the bane of my existence. I know they keep the kids safer, but they are so heavy! That being said, infant car seats are easy. The base is not necessary and I do not travel with it. It fits like the picture shows, over a rollaboard suitcase. That's how we transported it. Unfortunately, were never able to travel while Justin was in that seat, so I am not sure how it would work with Travis'. I still use a car seat for Justin on the airplane, but not for Travis. I carry them both through the airport with me and gate check Travis'. Since we travel stand-by, we never know if we will get on, and don't want the car seat to go and us not. And even if the flight has lots of seats, the airline doesn't have the same concerns about my children's safely as I do, and they don't care if my car seat doesn't arrive. I feel that if I take it to the door of the plane I have the best chance of it arriving with me. I know that is still not guaranteed, but that's a decision I have made for our family.
So, how do I get 2 convertible car seats through the airport? I am still learning. I tried using luggage wheels and strapped them both on it together. That works okay, but it takes time to strap them on. I use bungee cords for this. And it's not very stable. Very tipsy. I have debated getting a good sturdy set of wheels, but they are expensive. This past trip I just used the smart carts, except they are not always available at the destination. So that is out. This is my next idea, but expensive as well. It's a cart that hooks onto car seats (lots of models, I checked) and turns it into a stroller. I think I could just strap the other car seat on top and carry Justin, until he gets bigger. I am looking on Craig's List and other discount places. Renting a smart cart is $4 in IAH so really this would pay for itself quickly. And I am sure I could resell it. My boys are small, so they will be in car seats longer than most.
So I travel with: Justin on front, backpack on bag (this doubles as my purse/diaper bag during the trip), pulling large suitcase and 2 car seats. Travis walks with his backpack. I dress in light clothes because this is a workout for me! On the plane I have a backpack, car seat and the snugglie carrier. Justin is still rear facing since he is not 20 lbs. yet, but on the airplane he is forward facing since it doesn't fit the other way. I use a seatbelt extension to buckle it in. Ours fits without it, but just barely. It took me about the whole time the plane was unloading for me to unbuckle it the first time. A seatbelt extension gives the extra length to make it easier to unbuckle. Ask a flight attendant for this, and please return it when you are done. We always go to the bathroom before the flight since Travis hates airplane lavatories, and all three of us do not fit very well. I do not drink much, and neither do the boys, and we can usually make it the whole flight. The longest flight I have been on was three and a half hours, and Justin made three dirty diapers. So. not. fun.
As for toys, we only take toys for the trip, so things that we can play with while seated. The DVD player is the best! It really entertains Travis. I try to leave Justin in his car seat, if possible, so he accepts that he has to be there for the trip. I do not take "toys" for me (books, ipod) because I spend the whole time entertaining kids, and then I would just have to carry it for nothing. Maybe someday... Justin takes work! I admit that I often count the minutes until we arrive.
That's all I can think about now. If you have specific questions, please ask. I will do my best to answer based on my experience. I don't travel regularly with a pack and play, but we did once, and we packed ours in a bat bag to make it safer. We had to separate the crib part from the bottom board, but it worked. And I don't have to pay baggage fees (and our weight limit is higher), so my perspective is a little different. I have to say that prayer is now a huge part of my traveling. God answered mightily on this last trip, and I plan to give each travel experience to Him in the future. He took care of us FAR beyond safe travel. I was smiling on both ends of the trip, which is huge. It was safe and even a treat!