It may be the most wonderful time of the year, but when it comes to travel, it’s also the most chaotic time of the year. This year, travelers all over the world will face flight delays, cancellations, missed connections, and baggage loss during the winter holiday.
Traveling as a family can be a challenge even in the off-season, so to help you navigate, we’ve put together some family travel tips and winter vacation ideas perfect for everyone on your list.
Family Friendly Travel Tips for the Holidays
- Give yourself more time. As a general rule, when you’re traveling with a group you should always pad your itinerary with down time. This is especially true if small children are in your group. What’s worse than dealing with airport chaos during the holidays? Dealing with a two-year-old having a complete meltdown over a binki you left at home in the middle of the airport when you are already running late for your flight. So take time to pack and prepare. Arrive early. When it comes to traveling, you’ll want to build in time for delays and setbacks.
- Look for holiday deals & family travel packages. The holidays are a time for families. Everyone knows this, including travel providers. So starting in October, start looking for those holiday vacation deals and bundles. Remember, if you’re seeing the deal, so are hundreds of thousands of other people. Seize the deal, seize the holiday.
- Book an early, direct flight (and book it early). Statistics show that early morning flights have the best chance of leaving and arriving on time. This means less chance of having to sit for hours in the airport with impatient kids.
Additionally, if you book your flight ahead of time, you may get a smaller discount on your flight ticket. If you are looking to get travel insurance, that means it may cost less to cover it.
- Things may not go as planned, but travel insurance can help. You know those people who travel the world over without ever experiencing a flight disruption or baggage loss? Yeah, neither do we. While every parent wants to give their children a magical holiday experience, the spell can sometimes break.
Your holiday trip may have some bumps and snags, but trip insurance can help prevent it from becoming a real nightmare. Your kid gets sick before the trip? A winter storm prevents you from traveling? Luckily, trip insurance can cover those unexpected events. Additionally, trip insurance can also cover everyone under the same household in one policy.
- Make sure your kids know the holiday gameplan. Whether they admit it or not, children want to be told what to expect. So before you leave, sit down with your kids and walk them through the itinerary. This will help them feel more in control and excited about the trip. Better yet, if your kids are old enough, involve them in the itinerary building. They may come up with some cool sights and experiences you never would have imagined.
- Create some holiday magic. If you’re celebrating Christmas with small children, you’ll want to keep the magic of the season alive, no matter where you go. This is a lot easier to do in your own home, but traveling can actually help you create even more holiday magic. It all comes down to packing and preparing ahead of time. If you’re staying at a hotel, for example, dedicate at least one piece of luggage to holiday magic. Pack stockings, decorations, your Elf on a Shelf and, if your kids have one, a special plate and mug just for Santa. Check to see if your destination has any special festivities in the works. Your hotel may even help you line up a few holiday surprises.
Gift Packing Tips for Family Travel
There’s so much to consider when it comes to traveling with holiday gifts, we thought it deserved its own list:
- Avoid flying with gifts if possible. When you fly, there may be a chance that your gifts will be lost, delayed, or damaged.
- If flying with gifts is a must, don’t wrap them. The TSA guidelines are strict and they may rip open all your beautiful bows and painstaking creases.
- Make sure all gifts follow TSA regulations. If there are any liquids involved in the gifts, like for example a snow globe, the TSA may need to confiscate it.
- If traveling internationally, make sure the gifts can legally enter the country. Some countries have strict rules about what can and cannot be brought inside their borders. Usually, this pertains to food, but could apply to other things. Read your country’s entry restrictions carefully before you go.
- Pack and pad them carefully. If your gifts are fragile, wrap them in bubble wrap and surround them with your clothes. Though you might be asked if anything in your checked luggage is fragile, it doesn’t mean they’ll be able to protect it.
- Bring the receipts. If you’re visiting family and bringing gifts, make sure you bring gift receipts along in case your nephew already has that LEGO set or your granddaughter already has that stuffed animal.
- Have a strategy for hiding gifts from your kids. This goes back to creating some holiday magic. For kids who believe in Santa, nothing breaks the spell and spirit of the holidays like finding a trove of Christmas presents in the back of their parents’ closets, or in one of their suitcases.
Family Winter Vacation Ideas for the Holidays
New York, New York. There’s tree lighting in Rockefeller Center, ice skating in Bryant Park, and Holiday Markets in Union Square. Want a blast from the holidays past? Hop on The Nostalgia Train. Every year starting after Thanksgiving, the city’s straphangers can ride in holiday-decked subway cars from the 1940s.
London, England. London will always have a timeless charm to it, but it is extra special for the holiday season. Hyde Park has all sorts of winter events for families, such as ice skating, a circus, and even a Après-ski themed ice bar. London is also very walkable and has a great transportation system, which is perfect for families.
Quebec City, Canada. Quebec City is a place for families who want the cozy winter adventure. Quebec is known for its Winter Carnival, the largest of its kind in North America that is on many family’s bucket lists. You can also enjoy the comforting, warm food in Quebec, including poutine, tourtière (meat pie), and maple syrup treats.
St. Lucia, Eastern Caribbean. Want to rescue your family from sub-zero temperatures and knee-deep snow? St. Lucia might be just the ticket. Here you can find everything from light festivals, holiday feasts, and take part in other local traditions. And the best part is, you can do it all in a tropical paradise.
Aspen, Colorado. Aspen is full of fun for quite literally any person. From children’s snowboarding school to fine-class dining for the parents, Aspen is a festive area for the holidays while giving off a European vibe.
Festive Things To Do with the Family
Disneyfy your holidays. What could be better than celebrating the holidays with your family in the happiest place on earth? Prepare to be dazzled by light displays, and enchanted by the holiday parades. If theme parks aren’t your thing, there’s a holiday-themed Disney cruise waiting for you. Parents may think they’re doing Disney for their kids, but their inner children know better.
Visit a Christmas tree farm. Sure, you can always get your tree from the lot, but why not make an adventure out of it. Take the kids on a road trip to an actual Christmas tree farm. You can enjoy the festive spirit with the other tree hunters, find the tree perfect for your family and take it home. Who knows, it could be the start of a new holiday tradition
Take part in your destination country’s holiday traditions. Every country puts their own unique spin on the holidays. If you’re traveling internationally, read up on your destination country’s special traditions. If you’re in the Philippines for the holidays, you might want to check out the enchanting spectacle of Ligligan Parul (Giant Lantern Festival); In Iceland? Join in on Jolabokaflod (Christmas Book Flood), a Christmas Eve tradition where families exchange and unwrap new books, cozy up and read into the night.
Attend a Dickens festival. Don’t be a Scrooge. Take your kids to one of the many Dickens festivals across the country or around the world. Watch their wonderment as Charles Dickens’ A Christmas Carol takes place all around them.
Walk in a winter wonderland. From guided snowshoe-hikes in one of the country’s national parks, to frozen waterfalls in Quebec, there are many reasons to get out in the snow. So if you want to build a snowman in Croatia or have a family snowball fight in London’s Hyde Park or just enjoy winter wonderland in your own backyard, the holidays are the perfect time.
Do you Need Family Travel Insurance?
Whether they’re traveling domestically or internationally, American travelers have a secret weapon to make their holiday trips safer: trip insurance. If you’re traveling a distance typically greater than 100 miles, this coverage protects your trip investment. Lose your luggage filled with all the kids’ presents? If you insured them with trip insurance, you may be able to recoup that financial loss. Did a delayed flight cause you to miss your connecting flight? Trip insurance can cover related expenses like airport-to-hotel transportation, meals, and in some cases overnight hotel stays.
Trip insurance can cover those potential hiccups before, during, or after your trip while returning home, including the following:
- Trip Cancellation
- Trip Interruption
- Trip Delay
- Missed Flight Connections
- Emergency Medical Evacuation
- Accident and Sickness
- Prepaid/Non-Refundable Cost Insurance
- And More…
You can include everyone in your immediate family on the same policy as long as you and your partner are legally married and your children are under 18. If you’re traveling with extended family, they will most likely need to be on their own policy unless they’re minors and you have legal guardianship over them. However, if someone in your party will be returning home earlier or vacationing longer than the rest of you, they’ll need a separate policy.
Securing Trip Insurance for Your Family is Easy
Don’t let an unexpected situation ruin your holiday travel. If you’re ready to buy trip insurance or just have some questions, our Customer Success Team of licensed trip insurance experts are standing by to make sure your winter holiday travels stay merry.
Frequently Asked Questions (FAQs)
Is one family policy better than buying separate ones for each traveler?
It is much more convenient and cost-effective to put one family under the same policy instead of buying separate trip insurance for each traveler. The average cost of trip insurance can be about $50-$95 a week, which can make your trip cost significantly more if you decide to purchase individual trip insurance policies than what you need to actually spend.
Does it cover trip cancellations that are weather-related even if the storm hasn’t started yet but forecasts are showing a potential storm?
Weather-related cancellations have to be from either the airline or if the place you are traveling to has announced an emergency. If you are worried about a potential storm, it is advisable to purchase Cancel For Any Reason (CFAR) insurance. CFAR allows you to cancel for any reason, including any worries you may have, and recoup up to 50% to 75% of your trip costs. Cancel For Any Reason coverage is typically a time-sensitive add-on that needs to be purchased usually within 14-21 days of your initial trip deposit.
If the airline loses our baggage full of ski gear, can we get reimbursed?
Trip insurance can provide coverage for high-value items such as any ski or snow gear you may have if your baggage is missing. Typically, there are per-item and overall maximum benefit limits. Make sure to read your plan documents to understand the full details of what is covered and to what extent, since every plan is unique. Also, it might be worth it to consider purchasing additional specialty insurance for expensive ski gear.
If one of our kids gets sick right before the trip, can we cancel the trip and get our money back?
Absolutely. Trip cancellation can cover up to 100% of your trip costs if a family member falls ill or gets injured right before your trip, saving you the headache of potentially losing all the money you spent. When you file a claim for a trip cancellation due to an illness, you may typically need to present a doctor’s note confirming your child’s sickness.
If our return flight gets delayed overnight because of snow, will insurance cover the extra hotel night?
Yes, if your flight is significantly delayed because of a weather-related reason, trip insurance may cover your accommodation to stay one more night as well as meals for that time.
Can we insure just part of the trip, such as flights and hotels, but not local activities?
Yes, you can insure any expenses you wish to protect on your policy. All you need to do is enter specifically the amount you want coverage for. For example, if your hotel costs $1,000 and your event ticket is $400, and your primary concern is the cost of your hotel, you can just enter $1,000 in the cost that the quote tool will ask for. From there, the insurance options you will get will be specialized to a $1,000 coverage protection.
However, there are certain plans and companies that require you to disclose the full cost of your trip so it’s good to glance at your policy details or call your insurance company to understand what their requirements are.
Does the policy cover weather problems at home that disrupt our travel?
Yes, if there is a natural disaster such as a snowstorm or hurricane at home that causes you to not travel, trip insurance may cover you if you must cancel your trip.
It is important to note that you have to purchase a policy plan before a natural disaster is declared in order to be covered. Since trip insurance normally covers unexpected events, if you purchase a policy after a declared natural disaster, you may not be covered.
Can trip insurance cover my family if we want to go snowboarding or skiing?
If you plan to participate in a high-risk activity such as snowboarding or skiing, it is generally recommended to make sure that your insurance policy plan has an adventure sports add-on to cover your financial investment and potential risks.




