I don't know why we do it. I don't know why any parent with young kids does. It never turns out great in the end, but we all try it at least once: The Family Trip.
Our kids are generally pretty good. They can eat at restaurants without making a scene or forcing us to bust out tablets. They can ride in cars without much complaining or frequent needing pit stops.
In light of this, we decided plane travel would be fun. If you've never had the pleasure or flying with kids, I urge you to keep it that way. It's not, and never will be, a good idea.
They really should just ban kids under 10 from non-emergency plane travel altogether. Nobody wants to be around your kids on a plane. They fidget. They whine and cry. They require frequent trips to that tiny, disgusting airplane bathroom. If you've never had to help a kid with their pants or wipe their ass in a vertical coffin before, trust me, you aren't missing a thing. Travelling with two kids? Double the fun.
Think flying in the middle of the night makes sense because they'll just sleep the whole time? Dead f-ing wrong. In fact it's about a million times worse because they're overtired and you're tired and no one gets any rest of sleep. New colouring books last about 3 minutes on a five hour flight. The in-flight movie is almost never worthy of a 5 year old's attention. Especially if you're on a crappy Sunwing flight where the tiny screen flops down every 3 rows and the one in front of your seats is out of order.
In summary, the flight makes you need the impending vacation more than anything else in the world.
Oh, and if you kids happen to have a dairy allergy, bring enough snacks for a three week trek through the jungle. Everything on a plane but the saltine crackers has bloody cheese in it.
For our trip, we landed at about 8pm in Punta Cana. It was raining. It was another hour to the resort via shuttle. The kids thought it was a riot to fly down the highway in only big person seatbelts. It scared the living shit out of me.
Fun fact: When you get to a resort after 9pm, there's no welcome cocktail.
God I needed that cocktail.
They somehow lost a wheel on our stroller while in transit. If you have never tried pushing a 30 pound kid in a stroller with a missing wheel, I don't recommend adding it to you bucket list.
We thought we booked a 5 star hotel. This hotel was actually a 4 on the sign. I wouldn't have given it a 3. Our room smelled like pee pee. The beds were at least as old as me and had definite bows to them. The room faced the bar area where the party was happening. We were all miserable. And starving.
Food options at a shitty resort at 10pm? Cold french fries and cheese pizza. Fries it was.
After a fitful night of "sleep" in our oh-so-comfy beds and soothing bass-thump, I headed down to the front desk the next morning and moved us the hell out of there and to the five-star next door. Adios amigos.
After that the trip was pretty great.
By the way, if you do ever happen to want to take a voyage into hell's half acre with your kids, use the covered airport parking lot. Best $200 bucks we ever spent. When you get back into Toronto in the middle of January at 2am, you want that minivan of awesomeness close by and not buried in snow in some park 'n' fly lot you have to take a shuttle to. Trust me on that one.