How to Plan a Holiday Vacation With Less Stress
Lifestyle Travel

How to Plan a Holiday Vacation With Less Stress

Allie Johnson
Allie Johnson,Freelance Writer
Allie Johnson
Award-winning freelance writer with over a decade of experience.
LinkedIn Profile
11/03/2025 5 min read
Holiday travel planning can be a lot, but stress no more; we have put together 25 planning tips to help minimize holiday travel stress.
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While the holidays are hailed as the most wonderful time of the year, they also can be the most stressful — especially when you add a holiday vacation into the mix. However, it doesn’t have to be that way.
 
“Holiday travel is supposed to be fun and memorable, right?” says Marybeth Bond, a National Geographic author and travel expert at GutsyTraveler.com. It can be, if you plan ahead, she says: “A few extra minutes of thoughtful preparation before you leave home can save you hours of stress during your flight — or on the road.”
 
As you get ready for any upcoming holiday travel you may be planning, use these 25 holiday vacation tips to help you keep calm, save money, and enjoy your family and friends with minimal stress.
 

Booking Holiday Travel

1. Pay attention to timing. Timing your trip properly can help you reduce the cost and stress of flying. If you can, travel during the week and leave on a Tuesday or Wednesday. Avoid traveling on December 22 and 23, and instead consider December 24 (Christmas Eve) and December 31 (New Year’s Eve), both of which are typically cheaper days to travel during the holidays. December 26 also is a great travel day. If you’re an early riser, try to snag the earliest flight available. At the crack of dawn, airports are likely to be less hectic and airline employees more cheerful. Get your coffee maker and travel mug ready the night before and you’ll be good to go.
 
2. Use tips and tricks to save money on travel. Holiday travel can be expensive, so strategize to save money. Before you book a flight, monitor prices using a fare-tracking tool, such as:
 
If you have some flexibility, check Google Flights to see which days are cheapest to travel. Using rewards points or miles you’ve earned can be a great way to get a nearly free flight. But rewards travel during the holidays can be tricky, due to limited availability and blackout dates, which are days on which you cannot use your rewards. So be aware of blackout dates and book as early as possible, or try to use an airline whose rewards have fewer — or no — blackout dates.
 
3. Book a direct flight if possible. A nonstop flight might cost a little more, but it can prevent stress, missed connections, and having to pay for a hotel if you get stranded in a connecting city. Keep in mind that airlines typically don’t pay for lodging when passengers get stuck due to bad weather, which is the top cause of flight delays. In fact, snow, wind, ice, and other types of bad weather cause 69% of all delays. If you do have to connect, try to steer clear of New York, Chicago, and Philadelphia, which are the top three cities for weather delays.
 
4. Decide which car to drive. If you plan to hit the highway instead, should you rent a car or drive your own? There are several good reasons to rent, such as: You want to save wear and tear on your car, your vehicle isn’t right for the weather conditions or terrain at your destination, or you want extra room (or better gas mileage) for the trip. However, consider that it might take time to adjust to a new vehicle, and a rental will cost you more money.
If you do rent, contact your insurance agent to make sure your auto insurance covers your rental car. At The Hartford, our policies will automatically extend protection to your rental vehicle. In other cases, you may consider booking your rental car with a credit card that offers car rental insurance.
 
If you take your own car, make sure you have proper auto insurance coverage in case of an accident, theft or even a hail storm.

Giving Presents as a Holiday Traveler

5. Be savvy about traveling with gifts. If you’re flying with holiday presents, don’t wrap gifts with paper and tape (a gift bag is okay) because security screeners might have to rip off the paper. Also, make sure none of your gifts are prohibited by the U.S. Transportation Security Administration. Not sure? You can check the TSA “What Can I Bring?” page. Some items, such as baseball bats and cast iron pans, are allowed in checked luggage, but not carry-on bags, which is good to know before you pack. Carrying expensive presents like jewelry or a watch? Check to see if your homeowners insurance covers these valuable items or whether you need additional coverage.
 
6. Consider shipping gifts to your destination. Mailing gifts instead can lighten your load and save you money in checked baggage fees or make your carry-on easier to hoist into the overhead bin. One way to get your gifts to your destination at no cost and minimal hassle is to shop online with retailers that offer free shipping. Depending on your plans, you could either mail the gifts to yourself at your destination, then wrap and present them to the recipients in person, or choose the “send as a gift” option at checkout.
 
7. Give gifts that are easy to transport. Think about traveling light when you buy your holiday gifts. Gift cards are the obvious choice, and the good news is the majority of recipients would rather get a gift card than a physical gift. If you want a non-bulky gift that’s more personal than a gift card, consider a subscription based on the recipient’s interests. Ideas include:
 
  • Subscription boxes, featuring items that range from gourmet food products, to clothing, to gifts from around the world
  • Meal delivery plans
  • Magazine subscriptions
  • Coffee-of-the-month club
  • Audiobook, movie, or music service

Protecting What You Leave Behind

8. Secure your home. Whether you’re leaving for a few days, a few weeks, or longer, it’s important to take steps to protect your home and belongings while you’re gone. Most residential burglaries occur when the homeowner is away, so make sure you have the necessary protection with your homeowners insurance and a reliable security system, preferably one you can monitor from your smartphone. Also set up any services, such as snow removal, that will need to be done while you’re away. Piled up snow, or mail, could tip off burglars that no one is home.
 
9. Protect your car. If you’re leaving your car behind, make sure you have adequate car insurance. If you don’t already have it, consider adding comprehensive coverage, which offers covers “non-collision” damage from theft, vandalism, and storms. Before you go, park your vehicle in a garage or carport or use a cover to help keep it safe from hail, snow, and falling branches.
 

Getting Organized for a Holiday Vacation

10. Check on checked bag guidelines. Look at your airline’s checked bag requirements and fees before you pack. You can keep bag size and weight requirements in mind when you pack and avoid surprise fees. Remember that if you use an airline credit card to book your flight, you may get a free checked bag. If you have special items that could count as baggage, such as musical instruments or sports equipment, check with the airline in advance.
 
11. Don’t overpack. Forego bulky sweaters. If you need to attend an “ugly holiday sweater” party at your destination, you can always hit the local thrift store when you arrive. Use easy travel hacks to pack light. For example:
 
  • Pack layers made of merino wool for non-bulky warmth.
  • Choose a color scheme with no more than three colors to create a mix-and-match wardrobe.
  • Wear your bulky jacket and heaviest shoes to the airport.
  • Either buy your toiletries at your destination or take solid bars of shampoo, conditioner, soap, and shaving cream.
12. Keep contacts handy. Make a list of all the contact info you’ll need at your destination, including friends and family and your rental car agency, hotel, and tour operator. Put these numbers into your phone so they’re at your fingertips when you arrive. Also print this information on a sheet of paper to carry in your purse or carry-on bag in case your phone battery dies or your phone gets lost or stolen during travel.
 
13. Charge your devices. A fully charged phone is essential for travel, from presenting your mobile boarding pass at security to texting family and friends when you land. The night before your trip, fully charge your smartphone, tablet, laptop, e-book reader, and any other electronics you need for your trip. Many airports have too few charging stations, and it can be especially hard during peak travel season to find an outlet that’s not in use. For backup, consider traveling with a portable charger.
 
14. Gas up ahead of time. Whether you’re driving to the airport or taking a long holiday vacation road trip, don’t wait until you depart to fill up your tank. It’s no fun to look down and see a big E on your gas gauge when you’re tight on time to make your flight. And gassing up right before a long drive can delay you when you’re trying to hit the road early. So, fill your tank the night before you leave. Check GasBuddy.com to find the best prices on gas near you and to calculate the cost of gas for your trip.
 

Navigating the Airport This Season

15. Expedite your trip through security. If you travel regularly, consider joining a trusted traveler program such as TSA PreCheck® or Global Entry. As a member, you will be able to speed through security, and you won’t have to take off your shoes, belt, or jacket – or remove your laptop or liquid toiletries from your bag.
Tip: Contact your credit card issuer to see if they will reimburse you for the application fee.
16. Check in early. If possible, download the smartphone app for the airline you’re flying. You can use the app to check in 24 hours before your flight, which can save you time and stress. If you don’t have the app, you also can check in for your flight online. At that time, choose or change your seat if necessary.
 
17. Save time by using a mobile boarding pass or curbside check-in. Get your boarding pass on your phone, so you won’t have to wait in line to print it at the airport. Lines at kiosks can be especially long during the holidays, and this way you can skip right to security if you don’t need to check a bag.
 
If you do have to check a bag, you can avoid lines by using curbside check-in or see if your airline has a designated spot for dropping off luggage. To use curbside check-in, look at your airline’s website to see if the service is offered at your departure airport. If so, you’ll go to the curbside check-in desk just outside the airport entrance for your airline. You’ll need to present your photo ID and proof of your electronic reservation. If you owe baggage fees, you’ll have to pay those with a credit card. Curbside check-in is often free (though tipping is encouraged), but some airlines charge a few dollars per bag.
 
18. Fuel your body wisely. Packing healthy meals and snacks will help you avoid getting “hangry” on your holiday trip. Certain food items can go through security, but avoid foods not allowed though airport security, such as creamy dip, jelly, pudding, salsa, or vinegar. Stick with TSA-approved foods such as fruit, vegetables, sandwiches, power bars, chips, pretzels, and cookies. All foods except whole fruit must be packaged or wrapped.
Tip: Save pies for the holiday table, because they could bring extra scrutiny at security.

Taking a Road Trip for the Holidays

19. Brush up on driving safety. Before you go, check your car’s fluids, windshield wipers, and tire pressure. Make sure your navigation system is working. Prepare for bad weather and unexpected car trouble by stocking your car with supplies, including a blanket, flares, a jack, water, and a first aid kit. Review emergency driving techniques, such as what to do when you hydroplane. And be sure to get a good night’s sleep and check the weather forecast before you get behind the wheel.
 
20. Prepare for toll roads. Make sure you have some small bills and plenty of change in your car in case you end up on a toll road. If you live in one of the 16 east coast states that have E-Z Pass, consider getting a transponder for your car. With this payment system, you can sail through the toll booths and skip fiddling with coins in the cold.
 
21. Plan for car trouble. Chances are good that your road trip will go smoothly. But prepare ahead of time, just in case you do end up stuck by the side of the road. Consider Towing and Labor coverage, and add a help phone number to the contacts list in your phone.
The Hartford’s customers can call RESCUE 1-800® to access a network of 40,000 towing services nationwide. RESCUE 1-800® will still provide roadside assistance services to assist our customer even if they do not have towing coverage on the vehicle. In this scenario, the customer pays the provider at the point of service.
22. Map out your route. For safety and peace of mind, plan your driving route ahead of time, along with possible alternate routes, and share this information with a few trusted loved ones.
 

Minimizing Your Holiday Travel Stress

23. Bring tools for calm travel. Are you an anxious flyer? Try downloading an app that will help keep you calm while flying. For example, Valk offers calming exercises to use before and during the flight. Download apps before your trip, just in case you can’t get a Wi-Fi connection at the airport.
 
Learn a few travel breathing exercises to practice while you’re standing in a long line of cranky travelers or sitting in your seat waiting for takeoff. Here are three breathing techniques you can use to stay cool during holiday travel:
 
  • Inhale deeply and slowly through your nose, then exhale in the same manner for one minute.
  • Place one hand on your lower abdomen and the other on your chest. Slowly, gently breathe in through your nose so that your belly expands but your chest does not. Breathe out, feeling your stomach deflate. Repeat until you feel calm.
  • Use your right thumb to block your right nostril and inhale deeply and slowly through your left nostril. Block your left nostril with your right index finger and pause for one second. Lift your thumb and exhale slowly through your right nostril. Reverse the steps, inhaling through your right nostril and exhaling through your left. Repeat 10 times.
Plan ahead and bring diversions to help you pass the time more quickly and enjoyably. For example, you could bring:
 
  • An audiobook
  • An adult coloring book and crayons
  • Your favorite podcast
  • A book of crosswords, games, or logic puzzles
  • A quick-read paperback
  • A journal and a pen
24. Decide whether you need travel insurance. Flying to an exotic locale to celebrate the holidays? You may need travel insurance to protect you in case of trip cancellation or delay, lost luggage (with all your holiday gifts inside), or even a medical emergency abroad. And whether you’re driving or flying, check with your health insurer to make sure you’re covered at your destination and see what you need to know about seeking medical care away from home. Consider travel medical insurance, which may include additional benefits, like emergency transportation. Knowing you have the proper insurance to cover your trip will provide peace of mind.
 
25. Expect the unexpected. While it would be nice if your holiday vacation unfolded exactly as planned, chances are something will go awry. Try to build in extra time to deal with long lines, traffic, and other glitches. Think ahead, set realistic expectations, and mentally build in a Plan B for each scenario. For example, you might have your heart set on hitting the slopes at sunrise for a day of skiing, but the reality is that chronically late Cousin Sally may show up at 9 a.m. and then ask to stop for breakfast. Anticipating setbacks will allow you to take proactive steps to avoid problems or at least to take them in stride when they occur.
 
Of course, even the most diligent holiday vacation planning won’t guarantee you punctual traveling companions, cheerful TSA screeners, and good weather. But using these tips before you go can help you avoid many common holiday travel snafus, so you can relax and enjoy the spirit of the season.

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