Holiday Travel Tips to Make Your Boomer Travel Hassle-Free

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Many boomers travel to see children and grandchildren over the Thanksgiving and Christmas holidays. Or they book a holiday cruise to escape the season as Alan and I do on the years when we find ourselves alone for the festivities.

While you may be looking forward to celebrating the holidays with loved ones—or new-found travel friends—getting there can be stressful. Not to mention all the tasks that must be done ahead of time.

Don’t worry. I’m here with practical holiday travel advice to ease your mind. Although I can’t guarantee an uneventful trip, my holiday travel tips are the secret to arriving in a joyful mood.

The best holiday travel tips for boomer travelers

Gingerbread decorating hanging from a building
For some seriously strong holiday cheer, head to Strasbourg, France during the holidays.

Planning ahead, knowing what to expect and creating a crisis plan are my keys to a blissful holiday travel experience. If you follow these six holiday travel tips, you’ll be on your way to a blissful trip, too.

Holiday Travel Tip #1: Start your holiday travel preparations early

Luggage staged at the airport for a holiday trip
Who packs early? Smart travelers.

Whether your booking a house sitter or purchasing holiday air tickets, advance preparation for holiday trips makes for stress-free travel. How early should you begin preparing? I recommend at least six months in advance of your trip.

Plan ahead especially if you’re flying

What? You haven’t purchased your holiday airline tickets yet? Buying tickets as early as possible means better prices, more itinerary choices and a larger inventory of seats to choose from.

Watch for extra fees: Today’s holiday traveler must be vigilant when booking tickets to avoid hidden fees. Will you be charged for extra legroom, checked luggage, pre-boarding or printing your own boarding ticket? Is the ticket refundable, just in case the worst happens and you have to cancel? Extra fees add up. Know what you are purchasing to make sure the extras are worth the price. 

If arriving in time to celebrate the holiday is important to you, I recommend booking a flight that arrives a day or two beforehand. These days, flights are often overbooked. If you experience delays due to weather or a cancelled flight, that cushion of time might help you still arrive in time for the big day.

Choosing the best day to fly: I’ve found that Tuesday, Thursday and Saturday are the cheapest days to fly. You might consider flying on the actual holiday itself to save money, if the timing works for you. Most importantly, avoid peak travel dates like the Wednesday before Thanksgiving or the Sunday before or after Christmas (this goes for New Years, too) when tickets cost the most and planes are packed.

Boomer travel tip: Alan and I book our flights for early in the day, which allows time to be placed on another flight if ours is delayed or cancelled. 

Prepare your home for vacation mode at least one month before the trip

Before leaving on your holiday trip, be sure to use the preparing your home for vacation tips that I wrote for Cummins. In a nutshell, take steps to leave your home secure and prepared for bad weather, including finding a house sitter or a neighbor who makes occasional house checks.

Who wants their holiday celebration ruined by an unexpected power outage back home or a burglary because you forgot to arm the security system? 

Ship presents or pack them unwrapped

Three colorful bracelets
Sending those trinkets in the mail will not only lighten your load, but add some great excitement on the receiving end.

If you’re traveling to see family over the holidays, ship presents to your destination. With so many companies offering free shipping with a purchase, it’s the only way to go. And my favorite tip: pay a little extra to wrap shipped gifts. Have you ever wrapped gifts for a holiday road trip only to arrive with ripped gift packages? Enough said.

If you must bring presents on a flight, pack them unwrapped in a checked bag, then host a wrapping party with the family. The grandkids will love it. Not sure if you can carry it on the plane? Check the latest TSA guidelines.

Another gifting option is to give experiences that you can do with the family while visiting them over the holidays. Going ice skating, attending a musical performance or taking them to the game creates memories that they’ll cherish for years to come.

Holiday Travel Tip #2: One last check before heading out the door

Woman in a red coat checking her front door before leaving on a holiday trip.
Checking that front door, yet again. Yes, it’s locked.

Wait! Before walking out the door, have you checked that the flight is on time? Or what about road conditions? What’s the weather forecast? You know there are apps for that, right?

  • Download the app from your airline for updates and the ability to make itinerary changes on the fly. You’ll find it more responsive than waiting in line at the airline help desk.
  • Bookmark the department of transportation sites for each state along your route to make it easy to check current road conditions. Some states offer free apps. 
  • Keep up with the weather by downloading the National Weather Service (NWS) page (here’s how) to your home screen. For the most accurate weather forecast, I always consult the experts at NWS.

Of course the smart boomer traveler asks these questions several days in advance. Do you?

Holiday Travel Tip #3: Pack plenty of patience

Road climbs into the mountains
The roads aren’t always empty and the skies aren’t always clear, but the key to surviving typical travel setbacks is always patience.

Bring patience if you’re planning to travel during the holidays, whether that means a flight across the country or a road trip to the next state. Yes, something’s sure to go wrong—a delayed flight, poor road conditions, car trouble, or a crying baby sitting next to you on the plane.

Will patience overcome your travel woes? No. But patience will make a bad situation a whole lot better. That’s why it’s one of our top holiday travel practices for dealing with delays.

Dealing with flight delays and cancelled flights

Approaching the gate agent in a calm and patient manner brings more positive results than being a grumpy baby boomer. And you have downloaded the airline’s app for easier rescheduling when all the other passengers are waiting in a long line to reschedule flights, right?

If you made a list of alternate flights before leaving home, consult it now. Don’t rely on harried agents to come up with your best travel solution. Decide ahead of time how you want to deal with missed flights.

Road tripping patience

If you’re driving, be sure to load an electronic device with inspirational audio books or calming music before leaving home to feed your patience while sitting in bumper to bumper traffic.

Avoid mood swings by packing non-sugary snacks and bottled water. Popping a handful of candy into your mouth or sipping on a soft drink may give you a quick boost, but it won’t last long.

Decide on alternate routes before leaving home. And road trip apps are helpful for finding other routes, locating the next gas station or picking your parking spot.

Holiday Travel Tip #4: Be in the know

Man sipping coffee watching sunrise over the ocean
Don’t miss your first morning coffee at sea! Always arrive at your cruise port a day or two early.

If you really want to plan ahead, create a travel contingency plan. Write down a list of alternate flights in case weather cancellations happen. Have you downloaded the airline’s app or notated the 1-800 number for assistance?

For a road trip, map out a second route in case of road closures due to traffic accidents or weather events. Be sure to include hotel numbers for cancelling your reservation or making new ones along your route. Nothing’s worse than a no vacancy sign after a long day of traveling in the car.

Holiday Travel Tip #5: Arrive early

Two men changing a tires on the side of an Interstate.
Arriving early means that you’ll have some extra time to deal with unexpected situations.

This is not the time for a last-minute arrival at the airport. Getting there early, even earlier than the airlines suggest, reduces your stress level in case the TSA line is unusually long (you do belong to TSA Pre-check, right?) or the drive to the airport took longer than expected. Arrive early enough to enjoy a bite to eat. Alan and I use the extra time to walk the terminals for that last bit of exercise before a long sit on the plane.

One of the best ways to avoid holiday travel hassles is to arrive before everyone else starts to travel. Arrange your schedule to arrive a day ahead of prime travel traffic days. Then leave a day early or stay until the rush is over. If this is too much family togetherness, take a day trip to give everyone a break from each other.

When Alan and I travel to board a cruise over the holidays, we always fly a day or two ahead of the boarding date just in case weather delays us. We use the extra time to explore the port city before embarkation or rest up from all the packing and trip preparations.

Boomer travel tip: Shipping luggage to your cruise port is a wise decision during peak holiday travel. Who wants to have Christmas dinner or New Year’s Eve in the cabin because the airline lost their luggage? Not me. And if the fee is pricey, save money by shipping luggage to your cruise but schlepping it home with you after the fun is over.

Holiday Travel Tip #6: Wear a smile

Woman smiling following the holiday travel tip to wear a smile.
Take a breath, put on a smile, and don’t sweat the small stuff.

I know it sounds simple but wearing a smile is one of my favorite holiday travel tips. It may not solve your holiday travel hassles but a smile is guaranteed to make you—and those around you—feel a lot better about the delays.

Don’t be that traveler who works up an angry crowd by loudly complaining or spews gripes all over social media. Come on, it’s the holidays so spread a little cheer as you go.

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6 tips for a hassle-free holiday trip. Click the gingerbread man to read our holiday travel tips.


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