Traveling during the holidays is something I avoid. I cannot even remember the last time that we traveled around the holidays. My extended family all live within a half day drive, and my wife’s family lives…well. Let’s just say that I can see the in-laws house from ours. As Michael Corleone would say, keep your friends close, but your enemies closer.

Just kidding. I’m fine living across the street from them. Not to mention I’m already digressing. But as you can see, we have very little need to travel during the holidays. For those of you who will be jet-setting during this peak season, here are my holiday family travel tips if you’re among those headed off to see loved ones.

Holiday Family Travel Tips #1: Avoid The Holiday!

For those of you who find yourselves traveling every year over Christmas, you have my sympathy. Holiday travel can be some of the worst, as there are far more people flying than normal, some of whom barely ever fly. This can make the lines longer and more frustrating at the airport.

Which I why I suggest that you simply don’t fly over the peak holiday dates. A few weeks ago I was helping a co-worker price out cross-country flights around Christmas (as I’ve become the office travel guru). He was lamenting that everything reasonably timed and nonstop was $650 or more. Well…this is the price you pay for needing to travel right over Christmas.

So I suggested that they simply have Christmas early, pointing him toward a $200 sale over the second weekend of the December. He said that his sister would have none of it. Christmas needs to be celebrated over Christmas!

I personally would be totally open to celebrating holidays early or late, as needed, for both the financial reasons and to avoid the holiday travel rush. But if you must brace yourself to travel when everyone else does, here are a few other holiday family travel tips.

holiday family travel tips

Plan Out Every Transit Detail (Plus Contingency Time)

I’m generally not a planner. It is far more likely that I will have made air, car and hotel reservations, with little thought put into the other details of the trip until just a few days prior. If the backbone is there, I can usually make everything work just fine. I usually just have a list of ideas for what we’ll do and a departure time to make the flight.

But things go wrong. Kids throw up on the drive to the airport, or you get delayed in traffic. When time is critical and stress is high, it is far more important to plan out every detail of the trip: from when you’re leaving, to where you’ll get lunch on the way, to which lot you’ll park the car in for five days. This might seem like overkill, but the times that I’ve had a more concrete plan, things do go more smoothly. The predictability helps.

Adding in contingency time is something I’ve gotten out of the habit of doing. Sometimes we arrive early, other times we arrive just in time to pass through security and board our flight. However,  I’d plan to be extra early to the airport to deal with lines and any unforeseen problems during the holiday travel rush. You want to enjoy the experience, not be rushed, stressed, and frustrated all through the day.

Prepare Sufficient Snacks, Games, and Activities

I’ve not experienced flying with really little ones, but I have learned that failing to plan entertainment for the kids can frustrate you as much as it does them. I prefer flying Delta, as the airline still offers seat-back entertainment on most of their fleet. But in the event that we’re flying another carrier, I try to have enough entertainment loaded for the flight.

Don’t always count on the airline for seat-back entertainment or bring-your-own-device either! This backfired on me when my son and I were flying United from LAX to ORD. During boarding, the gate agents announced that the IFE was inoperable. There would be nothing. I hurriedly downloaded a single game on my phone (thank you, crappy LAX WiFi and cell service), which my son played the entire trip to Chicago.

But you can pack many things beyond the electronics. Before one of our trips abroad, my wife prepared travel backpacks for the older two kids. They contained a smattering of new toys, activity books, and coloring pads to help keep them entertained during the drive, at the airport, and on the plane. These don’t need to be much. You’re going for novelty more than anything. A few items can be enough to help the kids (and you) survive any long waiting periods.

My son also has a special travel animal that he always brings on trips. It not only provides him some entertainment, but a level of comfort as well. He hasn’t left home without Jeff the Penguin on any of our last several trips. Having the kids pick out a stuffed animal companion for all their adventures is a great way for them to enjoy their travels.

Snacks can be essential as well. As my kids are older, this isn’t as necessary an must for us. The snacks offered on board are usually enough to tide them over, and they know that we’ll eat again when we land. If flying international, the airline feeds us. If they don’t like it? Well, I’m generally a tough love parent. They can either eat what’s offered or choose to go hungry. Most airplane food isn’t especially good, but it’s been extremely rare that I’ve considered it inedible.

However, if I had really little ones, I’d be packing all sorts of snacks.

Making sure you have activities, entertainment and snacks for a trip isn’t just one of my holiday family travel tips, it’s a general travel tip. But during the stress of busy airports and the holiday rush, it’s even more essential.

holiday family travel tips

Check Those Bags!

I’m totally on #TeamCarryOn when traveling solo. I can’t stand checking a bag and having to wait for it at the other end (especially when I can make it through immigration and customs is 7 minutes flat with just a carry-on).

With kids, however, things are totally different. Well, partially. When it’s just me and one of them, we’ll usually carry on. More than one kid? Check those suckers. Having your hands free to wrangle kids and not bags is vital. Pack any essentials in small backpacks (the games, toys, snacks, etc.) and let them carry those.

There is the other side, where kids love being able to tote around their luggage. If this is your child, just make sure to keep it light. We’ve over-packed both carry-on and backpack before, and it is not fun, especially when you need to run through an airport. Their enjoyment of hauling their own luggage ends when it becomes tiring.

You absolutely lose time when checking bags. This is something you usually can’t avoid. But it does change my frame of mind as well. I’m no longer in a rush to get out of the airport. We’ll have time to grab a bite to eat and then head to baggage claim. I’ve often walked in during the middle of the bags being delivered onto the carousel, grabbed ours, and walked straight out. You can use the “delay” time doing something besides just waiting in baggage claim.

Make Sure You Have Some Sort of Insurance

Al my worst travel delays and cancellations have been during the winter months. I flew into Denver the year that Frontier had a total operational meltdown and people were stranded for days. Using a credit card that provides travel protections is even more critical during this time of year.

If you don’t have a credit card that provides reasonable trip protections, it might be worth buying travel insurance. Don’t do this through the airline, as it is generally not a good deal. It’s nearly always cheaper to purchase your own policy independently, and I’m considering an annual policy for next year.

There is also a cool new service called Freebird that lets you re-book your trip if things go wrong. If your flight is delayed, you can pick seats on any flights with any carrier still available. This gives you far more control than being at the mercy of whichever airline you’re flying. If you’re flying a low cost carrier with a limited network, it’s even more essential. This peace of mind is easily worth $19 per ticket, although I would be worried about facing carries with completely full aircraft traveling during peak times.


If you find yourselves on the road or in the air this season, hopefully these holiday family travel tips can help take the stress out of the travels. Personally, I would avoid it entirely if you can. But if you can’t, you can at least make it as bearable an experience as possible.