This past winter we decided on our first "family" vacation the three of us, we have done weekend trips to Montreal, Toronto & near Quebec City but we haven't done a big trip on a plane with time restrictions. The thing that saved us was planning ahead, I made sure we had diapers, a change of clothes packed in a carry on and had a thin coat with good walking shoes in the car to change into instead of bringing our winter coats and boots along with us too. Also we booked a direct flight to our destination, with a shuttle waiting for us, to bring us right to the car rental. I made sure to book our flight early in the morning so by the time we were on the plane it was her nap time and for our hotel room we had a separate room for Miss V so that she could not "see" us while she was trying to sleep. She will not sleep if she can see us or the TV.
My top FIVE must haves while traveling are;
Snacks; keeping a toddler distracted with food is so worth it, but not just any snacks. You want to pack snacks that are a little dry and have some salt, like gold fishes or veggie crackers because having there mouth get dry will mean they will want to drink alot of water which helps with keeping there ears from hurting and it allows the pressure to equalize.
Bring there favorite blanket or teddy from home, having a piece of home that reminds them they are okay and by having the smell of home will keep them calm too. Miss V has her favorite "dodo" (blanket) she calls it because she's a Frenchy haha.
A new colouring book with a only a few crayons kept her busy and didn't leave her with tons of options for colours or making a mess with a box of crayons. She was happy to have a something new to use.
Car seat backpack carrier, we debated getting one because we didn't really think it was necessary because we weren't bringing our normal leather car seat with us, we were bring our spare one so we didn't care if something happened to it, but this was an actual life saver! It was so much easier for my husband to put it on his back while trying to carry Miss V or the luggage, it was out of the way and mind you, we over packed so I was afraid we would be over the weight limits, I put some of our stuff in with the car seat bag and they never opened it, never weighted it or asked questions. When traveling with a toddler you get 2 free checked luggage; ie. car seat & stroller so we took advantage.
A few of her favorite toys & a couple beach toys. Having her own little toys from home made it that much easier for her to settle in. She kept busy in the car and in the hotel room while we were getting ready or packing for the day.