Traveling during the holidays
Travel,  Travel Hacks

25 Tips for Traveling During the Holidays

How to travel smarter during the holidays.

Traveling during the holidays is a big migration that’s felt around the world. Whether it’s for a particular event, or to reunite with family and friends. The undoubtable main objective is to have a pleasant journey and to arrive on time.

The first order of business before booking any travel accommodations and flights. Is to thoroughly research from reputable and official websites of both; the destination and the departure location’s government and your chosen airline’s regulations, rules and health safety measures and requirements related to Covid-19. As these change frequently.

For a deeper dive into travel hacks, check out 52 Savvy Travel Tips & Hacks.

This page has affiliate links to products. I may receive a commission for purchases made through these links but it’s no additional cost to you. As an Amazon Associate I earn from qualifying purchases.

Learn from my travel disaster

…. this experience taught me what NOT to do

When a dream vacation turns into a holiday nightmare of horrors. One learns very quickly to take proper measurements for the next trip. Years ago, I went on a 2 week vacation and booked both international and domestic flights. The route was; Washington DC > Caribbean > London > Maine > Washington DC. I was attending 2 weddings (one being my brothers) and having a personal holiday in between.

What was supposed to be a joyous celebrations turned into a calamity of travel diasters.

The airline canceled 2 flights (both mechanical failures at two different legs of the trip). Which caused me to miss my brother’s rehearsal dinner (in London) and miss a friends wedding in Maine. My luggage was lost for 2 days. When it was found, I had to drive 40 miles round trip (in DC traffic) to retrieve them. I also spent a total of 4 days of vacation in airports and airport hotels.

The aftermath of trying to receive any type of compensation from the airline was 2 weeks of back and forth arguing over my claim. I really do feel that it was a battle of who could hold on the longest. Nonetheless, it was agonizing and resulted in a few thousands dollars lost, complete distrust in the airline, and lost time of never being part of my brother’s rehearsal (but thankfully I made it to his wedding) and I missed my friends wedding.

Moral of the story. Learn how to protect yourself from travel failures. If I knew then, what I do now (e.g. booking, different types of insurance, airline loyalty, and much more). A lot of grief and lost monies could have been avoided.

Since that horrific experience, I’ve been on countless domestic flights around North America and 50-ish International flights (many of them super fun, quite pleasant and arrived on time).

I have yet to re-experience the nightmare above (knock on wood).

Savvy Tips on How to Travel During the Holidays

Travel during the holidays - planning

What to know before booking your flight.

To repeat above. Learn the most updated information of your destination’s and your government and your chosen airline(s) rules, regulations and safety measure in regards to Covid-19.

Before pressing that submit to cart button, check on the following.

TIP 1: Check your Credit Card’s Eligibility.

Find out if any of your credit cards provides a Priority Pass. This pass will give you free access to lounges or meals if you use their card to purchase your ticket.

Such cards are Chase Sapphire Reserve, American Express Platinum Card®, and Citi Prestige.


When travel fails happen (as they do), being insured is well worth having (& it’s inexpensive). They can protect you from flight cancelation delays, lost or damage luggage (and personal items), needed medicine or treatment, and much more.

Check your medical insurance. Domestic (US) health insurance may not cover you unless you have specific coverage. It’s not uncommon for people in the States to have travel insurance as an extra precaution when traveling domestically. If one gets hurt, they can file a claim with their insurance company and have the travel insurance pick up the deductible.

Definitely know the difference between travel insurance and travel protection!!!!!!!! The wording ‘vacation waiver‘ is also a term that’s has the same meaning as travel protection. And they drastically differ in coverage and benefits.

Travel protection / vacation waiver is offered by the travel company that sold you the travel service (airlines, cruises, rental car, etc). The travel protection will waive a cancellation fee (done by you – the ticket holder, not by the airline) or will provide a travel credit for a future trip. It will not cover a flight that is canceled or delayed from the airline. Some travel protection programs do have an insurance component, but it’s extremely limiting in comparison to travel insurance.

Travel Insurance is extremely useful when recovering monies for canceled, delayed, missed connection, lost or delayed or damaged bags, weather evacuation, lost passport, a travel company goes bust, credit card fraud, kidnapping, travel medical coverage (outside of your health insurance range; international travel), 24 hour service assistance, accidental death (kinda like a life insurance policy), dismemberment (I know it’s getting morbid), and much more is offered with the comprehensive package.

Many companies that offer travel insurance will offer two types: basic and comprehensive.

TIP: Lost luggage; you can be reimbursed in the range of $1-$1,000+ for lost items. But make sure you have pictures of your luggage and items. If you purchase anything on your trip and it was in your lost luggage, be sure to keep your receipt. It will be easier to have this information when you make your claim.

A fast and comprehensible comparison of travel insurances can be done with SquareMouth and

Popular travel insurance companies such as Travel Guard and World Nomads are both on Square Mouth and InsuranceMyTrip to compare.

When travel insurance may not be necessary;

  • Your credit card that you used to purchase your ticket, may provide travel insurance coverage.
  • Your health insurance may reimburse for incurred abroad trip hospital costs.
  • Homeowner’s policies may cover the lost of personal items (luggage, clothing).

If your flight options have layovers, consider paying more money for a direct flight. Tight layovers, checked luggage and making your connection have potential for traveling woes. Especially during the busy holiday season.

TIP 3: Be Mentally Prepared and Proactive.

Set your mindset to accept things can, and will not go according to plan. Be ready to course correct, when things go awry. I hate to sound pessimistic, but reducing high expectations that nothing will go wrong. Can lessen the shock and stress during holiday travel when they do. Brides – you know what I’m talking about (did that unexpected hurricane wipe out power during your wedding too)?

By being prepared and pragmatic with back up plans by empowering yourself with the knowledge of what to do and how to get access to it. Hence, having insurance when flights get cancelled. Downloading the right local Apps (if your hotel room gets canceled, shared car services – when no taxis are available, food delivery – hotel restaurants are closed).

TIP 4: Start a Checklist

The moment you book your tickets start a ‘Things To Do’ checklist, and add to it when more things pop into your brain. Allow it to be your holiday travel brain to keep you organized and on task. It will help with added holiday stress.

List anything you need to get done, like;

Turn on travel bank notification, figure out all back up plans to a canceled flight (surrounding airports, rent a car, take a bus?), pay bills, work stuff, medications, organize pet sitter, turn off all the appliances, give a neighbor a key, reschedule cooking class. ANYTHING – you get the point.

A checklist can prevent those uncertain wonders such as, ‘Did I turn off the iron?’ that creep into your thoughts at the airport or sitting on a plane.

TIP 5: Are You Cut the Line Pass Ready?

For US citizens, we can sign up and cut the lines at security with T.S.A. Precheck & Global Access & Clear. What are they and what are the differences? They are paid security programs that get you through security check points faster.

The difference between the three are TSA & Global Access are U.S. government programs. CLEAR is a private company that partners with T.S.A screening and does not require pre screen like TSA Precheck and Global Access. There are different payments for each, but all three are ways to ease through security a bit faster than the usual process.

For Global Travelers. Check your Airline Miles Membership status. You may have earned priority privileges perks for expeditious check -in and security pass, early boarding and or lounge access.

What to do before your flight.

TIP 6: Fill up on Gas

Driving yourself to the airport? Fill up on gas the day before your trip. This will prevent having to stop at a station on the way to the airport. Time is precious on the day of flying (especially during the holidays). Also, you will want to monitor the traffic.

TIP 7: Confirm your Back up Plans.

Confirm that all your plan Bs are ready to jump into action if a travel woe does happen. E.g. Your lovely neighbor will pick up your dog Snuggles, if your return flight is delayed.

TIP 8: Back up Your Phone.

Right before going on a flight, it’s a good time to back up your phone.

Have a look at traveling gifts that are light, life savers and are useful when NOT traveling.

TIP 9: Traveling with Presents.

Holiday or not. Bringing gifts to your host or family and friends is such a nice gesture. Just don’t wrap them (I know, it’s echoed across the interwebs), but it’s a good tip.

Consider ordering the items to your destination and have them delivered the day of, or after you arrive.

TIP 10: Get a VPN.

Get a VPN for International travel. Layover in China? You’re going to need that VPN. Especially if you’re a Gmail, Google, FaceBook, Instagram, Twitter user.

I live in Singapore and Netflix does not have the same options as it does in the States. The VPN I use is ExpressVPN and it’s very useful especially when I have multiple devices to use it on.

TIP 11: No Need To Pack A Lot of Clothes when…

….the destination has laundry machines. Besides how are you going to bring back your souvenirs and or presents?

TIP 12: Keep Yourself Entertained.

Whether it’s a layover, delay or cancellations. Or worse, there’s no inflight entertainment (broken screens or it’s a budget airline with no inflight entertainment; Scoot Airlines).

Bring a few options to occupy the mind. Maybe it’s work (boo!), a good juicy page-turning book, a podcast (or 2), the chore of clearing out a lot of photos in your phone, learning a language; Duolingo App, write in your journal, bring a pack of cards, find a little corner for yoga (if you’re stuck at the airport), get creative and write a short story or a letter to your future self or download some games or movies on your phone or tablet.

TIP 13: Pack a Self Care Kit.

Make a self care kit for your flight or use during a layover that fits your needs. My kit is similar to my husbands. He will have a power bank, cords, cell phone, a book, noise canceling head phones, chapstick, melatonin, eye mask, and ear plugs.

Mine will have the same items, I’ll also include a roller scent stick, a concealer, moisturizer, hair band, a toothbrush and paste, and a scarf or pashmina.

TIP 14: An APP To Keep You Updated on Your Flight. is a free App that will tell you everything about your flight. It will tell you where your plane is coming from, how close to the airport it is, and if weather is an issue.

It will also notify you, if your flight has gate changes, delays and cancellations.

TIP 15: Download Your Airline App or Program the Airline Customer Service Contact Information.

If the airline is delayed or canceled, have their customer service contact information programed into your contacts. You will be able to quickly call them while standing in line to speak with a ticket agent.

TIP 16: Stay Connected.

If you are traveling outside your mobile data and roaming plan. Decide if you will be getting a SIM card or check with your carrier’s data and roaming plans.

If you’re getting a SIM card, make sure your phone is unlocked (which you can have your mobile service do for you).

TIP 17: Pack Snacks and A Refillable Water Bottle.

Save money, give yourself a healthier option, prevent adult hangryness and or kid meltdowns. Most airports have a refillable station at the gate.

traveling during holidays power

TIP 18: Power Up Before You Go & Have Savvy Power Gadgets.

Along with having a power bank. A power cube or a multiple USB travel charger is super useful when charging multiple devices.

During holiday travel, it could be difficult to find an open outlet at the airport. It’s a great hunt that needs eagle eye vision and athleticism to be able to pounce on that elusive & coveted free outlet.

When an outlet becomes available, powering up multiple devices simultaneously with one little gadget will be your power up hero.

I love this International Power Cube because of the 4 USB feature. The bonus is, I also use a multiple charger cable. Super Win!

Another device that’s little and helpful is the Multi USB travel charger. Again, charging multiple travel devices simultaneously and only needs one outlet.

And all these devices can be used when not traveling. #LifeWin

TIP 19: Get a GPS Locator for Your Checked Luggage.

Or stick them in your kids pocket. Track your checked bags and never wonder where they are. Stick this handy GPS little device on whatever has the potential to wander off.

It’s also great to use when not traveling. Put them on your dog’s collar, or those keys that weirdly have legs or a wallet that likes to wander off too.

TIP 20: Check What’s Available at Your Airport and Gate.

Check the lay of the land before getting to the airport. Research your airport’s web page to see what’s available.

Know things like, the lounge and or the spa sitch. Are there movie theatres (I know, but it’s becoming a thing – check out what’s available at Changi Airport in Singapore) karaoke booths, sleep pods and other entertainment or rest areas in the airport.

Also, what’s around for the kids? Airports are becoming more kid friendly and having play areas to allow the kids to burn their extra energy.

Traveling Tips to use at the Airport

Tip 21: Get To The Airport Early.

It’s time for the hurry up and wait (in lines) during the great holiday migration.

Tip 22: Driving Yourself to the Airport.

If you elect to drive to the airport and leave your car in airport parking. Take a picture of your parking spot with the drivers license plate. As mentioned before, take a picture of any luggage that is being checked. This is in case your luggage is lost or damaged.

Tip 23: Put on Your Patience Pants and Good Music (or a podcast).

If anxiety starts to build, shift your thoughts and focus on what you are looking forward to doing or a person you’re seeing upon arrival.

Put on your noise canceling headphones and turn up it up. Drowning the outside noise pollution and replacing it with good mood making music or a comedic podcast can quickly change your mood and disposition.

TIP 24: Consider Paying Extra for Lounge Access.

Consider paying a daily rate for a lounge if the chaos around you is getting too much.

Tip 25: DO NOT TAKE any Sleep Aides …

….until you’re on the plane, at cruising altitude and the captain has turned off the seat belt sign.

You don’t want to be that person trying to navigate an airport, dealing with a canceled flight while on Ambien, Lunesta or any other sleeping aide. It’s a sure way to end up on a YouTube video that goes viral.

Extra Bonus Tip:

You can take that bottle of water through security (in the USA).

The caveat is, it has to be fully frozen.

Frozen liquid: Note from TSA

Frozen liquid items are allowed through the checkpoint as long as they are frozen solid when presented for screening. If frozen liquid items are partially melted, slushy, or have any liquid at the bottom of the container, they must meet 3-1-1 liquids requirements.” T.S.A.

A friend of mine used this tip when her husband had roundtrip business day trips, from SFO > LA > SFO. She froze soup for him for him to take for his lunch. #WifeWin

There it is. 25 travel trips to use when traveling during the holidays.

I know my personal horrific holiday nightmare experience is not as bad as others. But by taking certain measurements, can prevent one from losing a lot of money, sanity and faith that not all airlines are evil.

Safe travels and cheers to keeping calm and collected when traveling during the holidays.

Outdoor enthusiast thriving in the expatriate traveling lifestyle. Looking to connect with your sense of adventure.


Leave a Reply