How To Prepare For Your Winter Family Vacation

October 29, 2019

There are so many things to love about the holidays as a family — you get to be together with family, enjoying great food, possibly exchanging gifts. There’s a beautiful backdrop to winter holidays in particular, if you live in or visit snowy locations. However, the winter holidays are somewhat underrated in one regard. While everyone dreams about summer vacations, the concept of the winter family vacation has gone a bit overlooked, and is only more recently growing in popularity. This is in part because everyone is on to the idea of vacationing in the summer — which means that vacation spots are more crowded, and the rates for hotels and attractions are higher. People also are catching on to the fact that a winter family vacation is often easier to organize than a summer family vacation. For one thing, everyone wants to get the family together anyway when the holidays roll around. Why not make a full vacation out of it? Furthermore, while the kids are out of school during the summer, adults are still expected to work — it’s no wonder that 96% of American workers say that vacation time is important to them. It’s often easier to get time off at work during the holiday season, as a lot of workplaces shut down for the winter holidays anyway — you might as well take your vacation time when it’s most convenient.

Nonetheless, getting ready for a winter family vacation can be easier said than done. The last thing you want is to get to your vacation spot and realize that you’ve forgotten something back home, or neglected to take care of an important errand ahead of time. For that matter, the way you prepare for your winter family vacation needs to coordinate around the type of vacation you’re taking. You don’t have to break the bank in order to bring your family together over the holidays. A road trip to a scenic wintery location can help you experience a true, snowy white Christmas. Of course, although there are many advantages to taking a winter family vacation over a summer family vacation, there are certain aspects of traveling in the winter that you need to keep in mind — which just don’t occur during the summer. You should certainly start planning for your vacation well ahead of time. The more you take care of preemptively, the more you’ll be able to truly enjoy your time with your family. With that being said, let’s look into some of the steps you should take to ensure that you have the best possible winter family vacation.

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Make Sure The Family Is Ready To Go

As we previously mentioned, a winter family vacation is a trip that the whole family can enjoy. But at the same time, there is always a certain amount of organization necessary when kids and adults are traveling together. You can request off the necessary dates at work — but it’s easier to coordinate those around your kids’ school schedules than it is to attempt the opposite. This can become a bit trickier, of course, if your kids go to different schools. You should get your hands on everyone’s schedules right at the beginning of the school year — if not earlier. If you take the time to plan earlier, you’ll be better able to make it through any hiccups that might occur along the way. You should also make sure that your kids are on top of their schoolwork — the last thing you would want is for your child to have to worry about making up work during your winter family vacation.

Even more importantly, you need to stay on top of everyone’s health. Accidents happen, and sometimes you can’t prevent people from getting sick. But you should do whatever you can to prevent complications from happening over your vacation time. Furthermore, it’s important to remember that the winter holidays do happen to overlap with cold and flu season. Before you go on your family vacation, you should take your kids to the pediatrician in order to make sure that they have all of their vaccines taken care of. For that matter, you may want to bring a small first aid kit with you on your vacation — especially if you’re taking a road trip. You never know what might happen on the road, and the last thing you want is to have to take a detour for a band aid if your child sustains a minor cut on the road.

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Even if you’re saving money by taking a road trip rather than flying, you’re probably spending a good amount of money on your accommodations and reservations at attractions. If you’re really worried about what might happen if a health incident prevents you from traveling, you may want to look into travel insurance. If your winter family vacation is something you’ve been saving up for over an extended period of time, it may very well be worth it!

Getting Your Wheels Ready

So — how exactly are going to make your winter family vacation happen? If you’re taking a road trip, you may want to consider skipping the hotels and resorts altogether and going on an RV trip. If you don’t already own an RV, you might want to consider renting one. But if you’ve acquired an RV and are taking your first RV road trip, be prepared to make a lot of memories! RVs are perfect for those who want to go on a classic road trip. In a sense, it streamlines your vacation — rather than hopping from place to place, you can stay on the move and stop wherever you want. With that being said, there is a certain level of commitment required when undertaking an RV vacation. You have to expect the unexpected. Just as travel insurance may be a good idea if you’re worried about losing money on your accommodations, you should also consider RV insurance.

This is especially true when you’re traveling over the winter. There are two different philosophies when it comes to a winter family vacation — you’ll either be heading from a warmer climate to your perfect, classic wintery locale, or you’ll be running away to escape the cold in a balmier destination. Whether you’re heading towards the winter or away from it, you may very well encounter some snow and ice along the way. Therefore, you need to prepare your vehicle. Make sure that you not only have tires that are prepared to take on slick or snowy road — but spare tires besides. If you’re not taking an RV, some prefer to drive a truck rather than a car during the winter due to their durability and ability to weather storms. But the trade off there is space, making them less than ideal for bigger families. As over-cautious as it may seem, you should have your vehicle serviced and topped off when necessary before going on your winter family vacation. Have the battery checked as well, and if there are any concerns in mind you need to have them looked at. The last thing you want is for your vehicle to break down during your road trip. It’s even more concerning when this happens during the winter, when you may very well have to deal with extreme weather. You need to drive defensively, and perhaps over-cautiously. Expect other drivers to be less careful than you. Keep an eye out for road signs, and be aware of your surroundings; if you’re running somewhat low on gas, you’ll want to stop far before you get to the point where you’re desperate.

Remember — if you’re going on a road trip, comfort is also a concern. You’ll be in your car for a long time! Have your kids earn their vacation allowance by cleaning out the car before you drive. Of course, if the vehicle has accumulated a lot of damage over the years, you may be better off having a professional upholstery cleaning done before you go. Then again — depending on how well-behaved your family is you may be better off having that done after you go on vacation! All that being said, you should definitely set some behavioral ground rules before you hit the road.

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Take Care Of Your To-Do List

The last thing you want is to have an amazing time on your winter family vacation, then come home to a disgusting house. Make sure that you have your trash all cleaned out and picked up before your vacation — depending on how your trash pickup works and how long your vacation is going to be, you may also want to let your trash pickup service know as well. The same goes for most delivery services and subscriptions. You don’t want anything to be delivered to your front step and left outside, where it could be stolen or damaged by the elements. If you can’t have your mail held at the post office, ask a neighbor or friend to take care of it for you. If you’re gone for a good amount of time, it may be a good idea to pay someone to house sit for you. This may be especially important if you live in a colder area — it’s all too easy for your pipes to freeze during a cold snap, and that could wreak havoc on your home’s plumbing. You would be surprised by what could happen when your house is left on its own; though you may not want to pay someone to check in on your house, you’re definitely better safe than sorry.

You’ll have even more to worry about if you have a pet, of course. If you don’t know anyone personally who can watch your pets for you, it can be nerve-wracking to decide what to do. Should you board or work with a pet sitter? While it may be tempting to board your pet, in recent years many boarding kennels have come under scrutiny. A lot can happen if you drop your pet off at a kennel. With that being said, there are plenty of kennels that are reputable and caring — you just want to seek recommendations from your veterinarian. However, it may be easier to have a pet sitter visit your house, especially if your pet is prone to anxiety. Having a pet stay at a kennel can be a highly stressful experience; at least with a pet sitter they get to stay in their familiar surroundings! Of course, if you do decide to go down the pet sitter route, you’re entrusting them not only with your pet, but access to your home (unless the pet sitter is keeping your pet at their home). Therefore, you’ll want to get to know them well before you go on your vacation. The great thing about a pet sitter is that they will probably offer a personal touch that a kennel often can’t; but again, this can be up to personal preference.

No matter what you decide to do for your family winter vacation — whether you decide to go on a road trip or simply fly out to visit your relatives — preparation is key. Most of us only get to go on one or two vacations each year. You’ll want to make the most of your vacation time, so that you can kick up your feet, relax, and enjoy your time with family. Remember — that’s what it’s really all about!


Caroline is a freelance content creator and creative writer. VCUArts alum with a focus on the arts, travel, and culture.



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