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How to Prepare for Your Winter Family Vacation

Snow-covered cabins, beautiful twinkling lights, and crisp air—the winter family vacation is always an exciting event to look forward to, but sometimes it’s difficult to nail down the details.

From knowing exactly what you need to pack to what you’re going to do, planning it ahead of time will help you make the most of your adventure.

But don’t panic when getting ready for your winter getaway. Whether you’re headed to Toronto or Aspen for your winter family vacation, we have you covered with a guide for how to best prepare.

Planning Your Itinerary 

As with any trip, your itinerary is the most important aspect of having a successful winter vacation. Once you know your destination, begin thoroughly researching things to do, where to eat, and things you can’t miss. Have each family member put together a shortlist of what they’d like to do. Compare the lists and see where they overlap and then take into consideration the most realistic plans for your trip. You want everyone in your family to have fun, so make sure at least one thing from each list makes it into the schedule, even if you have to go a little out of the way to make it happen.

Figuring out an itinerary that makes sense will save you time and money. After all, you don’t want to be trailing back and forth when there’s a logical way to go about your must-see stops. While you don’t have to plan your trip down to the hour, having a rough idea of what you’ll do each day will help you make the most of your time.

Make sure you also have a backup plan in case of inclement weather. Preparing ahead of time by stocking up an extra vacation day or two and knowing what you’ll do if you can’t your flight will save you a lot of headaches.

Packing Your Bag

The other important aspect of your winter family vacation is packing everything you need. Let’s dive into some of the seasonal essentials you need to pack,

Winter Sports Gear

If part of your trip is going to involve any sort of winter sport, you’ll need the right gear. From sledding to shredding, remaining warm and dry should be top of mind. While you might be able to rent, bringing your own will save you the headache of sizing and quality issues.

However, if you’re flying, you’ll likely need to make arrangements to rent a snowboard or skis, boots, and a helmet. You can bring along your own snow sports essentials though, such as:

If style is a priority to you, bringing along the right wardrobe is even more important. Fortunately, you can choose from chic retro ski suits and the latest snowboarding gear to look your best. If the sole purpose of your trip is to hit the slopes you may want to indulge yourself and bring your own gear, snowboard bag, and all, just keep in mind that it could increase the cost of your flight and make getting around more difficult.

Warm Clothing 

The key to staying warm on your winter vacation is layering. So what clothing pieces are necessities and which can you leave at home? Our top wardrobe must-haves include:

  • Long sleeve shirts
  • Short sleeve shirts
  • Sweaters
  • Versatile jacket or coat
  • Several pairs of pants
  • Full-coverage pajamas

These items should be easy to layer so that you can make sure you’re warm, but not too warm as needed. If you’re going to be spending the majority of your time outdoors, you’ll want to prioritize outerwear that’s weatherproof.


Winter weather accessories are a necessary addition to your basic wardrobe in order to stay warm and comfortable. After all, traveling while uncomfortable, is one of the easiest ways to put a damper on your vacation. We suggest the following as a starting point:

  • Scarf
  • Gloves (you may want to bring one knit and one leather pair for different occasions)
  • Several pairs of socks
  • Hats (make sure at least one covers your ears)
  • Shoes (if you can get it down to one pair it’s highly recommended so you don’t have to waste luggage space)

Choosing items that can be dressed up or dressed down will be your best bet for keeping it minimal while maximizing functionality.


Last but not least, you’ll need to pack your toiletries. Above and beyond the basic toothbrush, toothpaste, and other essentials, there are some special recommendations to consider, including:

  • Chapstick (high winds can really dry out your lips)
  • First aid kit (you never know when you might need a band-aid on the road)
  • High-quality sunscreen (even if there won’t be any sunshine, you can still be exposed to UV rays)

If you found this guide helpful, don’t miss out on our tips for summer travel for your next family vacation.