STRESS-FREE HOLIDAY TRAVEL: 5 MISTAKES TO AVOID THIS CHRISTMAS SEASON
Updated: Aug 27
Every year, the holidays seem to sneak up faster than expected, and for families who love to travel, that can mean trying to balance festive fun with packing lists, flight schedules and maybe even a few meltdowns along the way.
Over the years, I’ve experienced both ends of the holiday travel spectrum: from the magical energy of Disney World during Christmastime to a quiet Christmas spent in a remote mountain village in Northern Thailand.
That year, instead of exchanging gifts, the people in the village showed us their traditional Thai clothing and we handed out stickers to local kids. It was a completely different kind of Christmas and a reminder that some of my favourite travel memories have come from experiences I never could have planned at home.
Whether you’re escaping the cold, heading somewhere snowy or spending the holidays at a theme park, a little planning can prevent some surprisingly common travel headaches. Here are five things to think about before you pack your bags.
SHOULD YOU WRAP CHRISTMAS GIFTS BEFORE FLYING?
It’s tempting to arrive at the airport with your gifts beautifully wrapped, but Canada’s Air Transport Security Authority (CATSA) recommends keeping them unwrapped. Security officers may need to inspect them, which means your perfect bows could end up torn open.
Instead, pack a small roll of wrapping paper or gift bags in your suitcase and wrap your gifts at your destination.
If you’re travelling internationally, consider giving experience-based gifts, like excursions, photos, or small surprises that celebrate the trip itself. It’s one less thing to carry through the airport.
If you’re still looking for something to pack under the tree, my Ultimate Family Travel Gift Guide has holiday gifts and stocking stuffers for kids and families who love to travel.
HOLIDAY TRAVEL GETS BUSY EARLIER THAN YOU THINK
Peak travel dates around Christmas can mean packed airports, full flights and long security lines. And the effects of holiday travel can start well before Christmas week.
When I travelled to Disney World with my family in November to experience the holiday magic, it wasn’t technically Christmas week, but my parents’ flight was cancelled the night before departure, and they ended up arriving a full day late.
Thankfully, they’d built in a buffer day before our first park reservation. Otherwise, that would have been a very expensive travel hiccup.
AMANDA'S ADVICE - Give Yourself a Buffer - Don’t underestimate how one flight delay or cancellation can affect the rest of your plans. When possible, choose early-morning departures and arrive at least one day before anything you absolutely cannot miss. This is especially important if you’re heading on a cruise or have prepaid experiences waiting for you.
DON'T LEAVE HOLIDAY PET CARE UNTIL THE LAST MINUTE
If you have pets, don’t wait until December to arrange care. Kennels and sitters book up early, especially around the holidays.
We’re lucky to have family who can help with our dog when we travel, but I know that’s not the case for everyone. Whether you’re boarding, hiring a sitter, or asking a friend, book early and confirm the details in writing, especially for longer trips.
QUICK TIP - Leave behind a small pet-care kit with your vet information, feeding routine, medications if applicable and an emergency contact. It’s one less thing to worry about if plans change while you’re away.
HAVE YOU CHECKED YOUR AIRLINE'S BAGGAGE LIMITS?
Between gifts, winter or summer clothes and souvenirs, family luggage fills up fast. Baggage allowances and fees can also vary by airline and fare, so check the rules for your specific flights before you start packing.
As a family, I’ve learned that a portable luggage scale is an absolute must. Our suitcases are often overweight before they’re even full, thanks to all the “just in case” extras parents tend to pack.
AMANDA'S ADVICE - Weigh Your Bags Before You Leave - Weigh your bags before heading to the airport and keep one foldable tote handy for overflow. If you’re travelling as a multigenerational group, coordinate packing lists ahead of time too. One of my client families travelled to Disneyland with 11 family members, exactly the kind of trip where everyone bringing duplicates can add up quickly.
Planning a trip with grandparents, parents and kids? My Planning a Vacation with Kids & Grandparents blog covers some of the decisions that are especially important when several generations travel together.
DO YOU REALLY WANT TO PLAN EVERY HOLIDAY TRAVEL DETAIL YOURSELF?
Between flight schedules, connecting rooms, dining reservations and changing airline policies, holiday travel can come with a lot of moving pieces.
You absolutely can plan it all yourself. But during an already busy time of year, do you really want to spend your evenings comparing flights, resorts and room categories?
Working with a travel advisor can take some of that research and coordination off your plate, especially for more complicated trips involving cruises, Disney, multigenerational travel or multiple rooms.
For busy parents juggling school, work and holiday wish lists, sometimes the biggest benefit isn't simply having someone book the trip. It's getting some of your time back.
A LITTLE HOLIDAY TRAVEL PLANNING GOES A LONG WAY
Holiday travel will probably always come with a few things you can’t control—a delayed flight, a change in weather or a suitcase that somehow gained five pounds between your bedroom and the airport.
But a little preparation can make those surprises much easier to handle.
Leave the gifts unwrapped. Give yourself extra time. Arrange pet care early. Check the baggage rules before you pack. And if planning all the moving pieces is starting to feel like another holiday job, remember that you don’t have to manage every detail yourself.
Some of my favourite holiday travel memories have looked completely different, from experiencing the Christmas magic at Disney World to handing out stickers to children in a small village in Thailand.
Neither trip went exactly according to plan, and that wasn’t what made them memorable. What mattered was having enough room in the plans to actually enjoy where I was.
And that’s what I want for my clients too: a holiday vacation where you can spend less time worrying about the logistics and more time enjoying the trip you worked so hard to plan.
PLANNING ANOTHER FAMILY VACATION AFTER THE HOLIDAYS? My Ultimate Guide to Planning a Stress-Free Family Vacation with Kids walks you through the bigger planning decisions and is a great place to start.
If you’re still gathering ideas for your next family vacation, come join my free Facebook community, Elevated Family Vacation Planning with Amanda | Disney, Cruises & Mexico.
You’ll find practical family travel tips, destination inspiration and conversations about Disney, cruises, all-inclusive resorts and the decisions that come up long before you pack your suitcase.
Wherever your holiday travels take you this year, I hope you have a safe and wonderful holiday season.
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