Holiday Travel Tips – Make Holiday Travel As a Family Less Stressful

This the season…to grab a car, train or plane to hop out of town. Often, it’s to see far flung family, but it can also be just to take advantage of the school holiday and travel somewhere fun and festive this time of year. But traveling this time of year, especially in the United States where it’s winter, can be stressful. Loads of people who don’t travel very frequently taking space and time, short staffed airports and train stations due to the holiday, and weather can all put a damper on your travel plans. Add in a few cranky kids and it will make you wonder why you ever decided to leave the house. But have no fear, with some planning and these tips, you can have a fun, less stressful holiday, and help create the magic of the season, no matter where you spend it.

*Disclosure: This post may contain affiliate links that allows me to earn a small commission at no cost to you. I only link to products I would or have used myself and all opinions expressed here are my own. You can read the full disclaimer here.

A young boy and girl in front of the Santa by the bay in Keyport, NJ

Planning

Whether you are traveling to be with family or using the school holiday to get out of town and travel somewhere over the holidays, one of the most important steps you will take is planning. Planning any trips is important, but if you are traveling during the holidays, planning can make or break your trip. Some things to consider: 

A young girl in front of a Santa pulled by a horse drawn carriage
  • If you are reading this when it first posts, the likelihood you have already planned the trip. But if you are reading this later, note this:  PLAN EARLY!!!  If you are flying, book tickets 6 months before your flight. Staying in a hotel, reserve a room 3 months early. The holidays are a very popular time to travel, so if you don’t want to pay the same cost as a kidney, the earlier, the better to get the best prices.
  • Choose your timing wisely. Flying mid-week will be cheaper and less busy. Flying on Christmas Day and early New Year’s Day actually is pretty cheap and again less busy. Driving a few days before or after Thanksgiving, Christmas Eve, and New Years Day will help you avoid some of the traffic.
  • Talk with your kids about how the holidays might be different since you won’t be home. See what they love about spending the holidays at home and see if you can help include those traditions while traveling. In 2020, when we spent a month in New Jersey, the kids wanted to make sure we still made Christmas Cookies. So we Instacart-ed all the items we needed, and took over my Dad’s kitchen for the day. Everyone quarantine-ing with us got to enjoy yummy Christmas Cookies.
  • Visiting family from out of town?  Check the town website, business association, and/or public library for local holiday events that you can take part in. My kids got to receive a visit from the local Santa, an event run by the fire department in town.
  • Visiting a new place for the holidays?  Check out what cool tours and special seasonal events are available. We got to attend the Christmas Wonderland at the Maple Leaf Farms in New Jersey. In the Bay Area?  Check out Glowfari at the Oakland Zoo or the Santa on Segways Holiday Segway Tour. Or book tickets to the Nutcracker with the San Francisco or Oakland Ballet.

Flying

Flying during the holidays is just chaotic, it just is. Here are a few things to keep your sanity in check.

A young boy surrounded by bags a the airport
  • Arrive at the airport one hour earlier than you normally would. I personally shoot for 1.5 hours prior to my flight, but in the holiday season I arrive 2.5 hours before. If you are checking luggage or flying with a pet, give yourself an extra 1.5 hours. (for me that would be 3 hours before). Lines are longer, and everything is just a bit more chaotic.
  • Make sure to keep anything that MUST arrive with you in your carry-ons. Maybe that’s the clothing you need the first few days. Maybe it’s the expensive gifts you want to make sure arrive. But whatever absolutely must arrive needs to be in those carry-on bags. It doesn’t have to just be in your carry on, feel free to spread it out among family members. But there is a lot of baggage going through the system during the holidays and some of it will get lost. Speaking of lost bags…
  • Invest in Air Tags or Tile Trackers. This summer my mom’s bag was lost by Aer Lingus for over 25 days. Afterwards, we invested in these Title Trackers. We lost a bag on the way back from New Jersey, and could see where it was thanks to the Title tracker we dropped inside of it. In fact, the next day I went to check on where the bag was and was surprised to see it it’s location was our house. I looked out the front door and saw it on the porch. It had been delivered without anyone ringing the bell!  I’ve seen in my travel groups a number of people who were able to let the airline know that the bag had arrived and was somewhere in the building thanks to these tags.
  • There are tons of blogs with tricks for keeping little ones entertained on the flight. (You can ready my popular post about Traveling with an Older Lap Children) Make sure to check those out before flying for the first time with the little ones so you are ready. But most importantly of all the advice, remember this. You will likely never see these people again, so don’t worry about the judgement, they don’t matter anyway.

Driving

Flying during the holidays can be very expensive, so many of you will choose to drive to the destination of choice. Some of you will be lucky enough to be driving where it’s always sunny. Most of you won’t.

A snowy car parked on the street
*
  • Make sure your car is ready for any winter travel/long road trips. Holiday hours will affect everything from tow trucks to mechanics. Make sure to make your appointment for a tune up well in advance, and make sure your car is in tip top shape before you go. The last thing you want is to be stuck on the side of the road in the snow with kids in the car waiting hours as roadside assistance is looking for someone who has a tow truck available.
  • Pack some emergency items in your car in case you do break down. Have snacks, a blanket, snow scraper (even if you never use one), jumper cables, etc. If you do break down, you want to be prepared because the wait for help will be longer than usual.

Lodging

Whenever you are traveling, you aren’t staying in your home bed. Here are a few tips to make it as comfortable as possible.

A young boy and girl sitting in Christmas Pajamas in a hotel bed
  • Hotels will be understaffed at this time of year. Everyone wants to spend time with their families this time of year. Have patience with the staff, they are trying the best they can.
  • Check to see what special events they have for the holiday. We were pleasantly surprised to see our hotel in Washington DC was having a free brunch in the lobby on Easter Day. Hotels often have these special touches, especially in areas where they get a lot of tourists during the season.

Holiday Gifts

Part of the wonder (and difficulty) of this season is presents!  Wherever you are going, you are likely to have one or two presents you will need at the location. Here are a few things to keep in mind:

A young boy and girl in Christmas Pajamas opening presents in front of the tree
  • If you are flying, make sure to pack the gifts UNWRAPPED. TSA will unwarp the gifts if something suspicious comes up in the screening.
  • Amazon Prime and other sites that ship are your friends. Feel free to ship your presents directly to where you are going. Especially if it’s a family or friend’s house. Just make sure to tell your host. Going to a hotel?  Call to check, but generally they will accept packages that arrive a day or two before you do. Airbnb?  Check with the host and see if they would be willing to hold a package for you if it arrives within a few days of your arrival. It’s really host dependent, but it’s worth messaging and asking.
  • Have older kids?  This is the year to gift experiences and small items. It’s ok to tell your kids the trip is the gift. Not only is it less to pack, but it makes for less being lost in transit. And as the Grinch said “Maybe Christmas doesn’t come from a store. Maybe Christmas… perhaps… means a little bit more!”

Gear Up

Traveling during the holidays and during colder months in general, can usually require a little extra gear:

A toddler asleep in a pack and play
  • While I normally recommend carry on only, if you are traveling to see family, just assume you are going to check in a suitcase. I have gone so far as to put a carry on suitcase in the checked suitcase on the way there, and separated it out to make space on the way back. Yes you can ship items, but I’m guessing you’ll get more value by paying the checked back fee and being able to fill your suitcase up to 50 lbs. You can also do one of these foldable duffle bags that you throw in you carry on, then fill up and check on the way back home.
  • When packing for colder climates, think of layers over thickness. Merino wool is so light and so warm. Thermals under your clothing will help keep you warm all day. And a packable down jacket (I love this one from 32 degrees) takes up very little space, but keeps you warm all day.
  • Think about the gear you might need to be comfortable, especially if you have a baby or toddler. There is plenty of travel or portable gear such as portable pack n’ plays, high chairs, etc. you can bring while traveling. You can also look to see if you can rent the equipment you need at the location, which is nice because it’s less you have to pack.

We have traveled a few times to the East Coast in the December Holiday season. We have even traveled internationally on Thanksgiving Day. It was never as easy or straightforward as our normal travel. But it was always fun, and it was always, always worth it. Seeing my kids enjoy Christmas morning with their cousins, enjoying New Year’s Eve with my family in New Jersey, having Thanksgiving up in the mountains with friends, have always added memories that live in my kids and my mind forever. The biggest piece of advice I can give you this holiday season is remember to be flexible, be patient and take the time to be present and enjoy. They are only little so long. These travels will be core memories that they will take with them all their lives.

Interested in Seasonal Tours and Activities in the city you are visiting? Check out Get Your Guide, who aggregates tours and experiences in cities all over the world

19 Holiday Travel Tips for Families

* Starred Photos taken by Atma Photography

Editor: SKS (Son)

Leave a Reply