Winter Vacation Ideas for 2020

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Winter is fast approaching, and excitement is building for cold-weather vacations! If you and your family are planning a trip this winter, these ideas are sure to inspire you and get you ready for traveling, spending time together and adventure!



Take a Ski Trip 

If you and your family have never been skiing before, this winter is the perfect time to start! Zooming down slopes with your loved ones is an experience like no other. You’ll get a truly unique adrenaline rush as you take in cold, fresh air and pick up speed. There’s nothing quite like it!


Staying at a ski resort with your family is an unforgettable experience as well. If comfort is a priority, staying at a resort will make your trip perfect. Many resorts are all-inclusive, meaning you and your family just have to bring the essentials, and the hotel covers the rest! If staying at an all-inclusive ski resort is within your budget this year, go for it. It’s well worth it and will provide a relaxing and recharging vacation for the whole family. 


When getting ready to take a ski trip, especially for the first time, it’s important to do your homework. Watch skiing-related videos and read articles in preparation for your adventure. There’s no shame in being a beginner – everyone has to start somewhere! And taking a vacation is the perfect opportunity to try something new as a family. 


If you’re a seasoned skier with years of experience, you’re already good to go for a ski trip this winter. The biggest task for you is planning your trip – it’s always great to go into a vacation with an itinerary. Even if you prefer to be spontaneous and play it by ear, everyone needs a little bit of a plan! 


Sit down with your family and discuss what everyone would love to do most while on your trip. With this info, you can build the perfect ski trip itinerary. Keep each member of your family in mind when planning, remembering that the vacation is for everybody to enjoy!


Head for Warmer Weather 

What if you’re not a big fan of the cold? Have you been dreading the approach of winter? Don’t worry, there’s a vacation out there for you, too. If you and your family are fans of warmer weather, pick a vacation destination somewhere untouched by the cold. 


If you are living in a colder part of the world, the winter can get a little stale. It’s only natural to want to bask in the sun on a beach somewhere when things get chilly. Even if you have to hop a plane to get to that warm, sunny spot, it’s well worth it. 


If you and your family love road trips and want to hit the road and go somewhere warmer, enjoy the journey! Time spent in the car with family is always a gift. There’s ample opportunity for conversation, games, or just sitting and enjoying each other’s company. Sometimes, the ride to your destination is the best part of the trip! 


Have a Staycation!

Sometimes, the best times in winter are spent with family gathered around a fireplace, sipping hot cocoa and playing games together. Vacations are for resting and recharging, and you don’t need to go anywhere to have a great time. Spend time with your family at home, doing whatever you and your loved ones love to do together. Watch movies, make art, and just chill out.


You can still be intentional and go all-out when planning a staycation, just like you would for a regular vacation. Make an itinerary with your family and enjoy different activities every day. You’ll be amazed by how much fun you can have at home!


When it’s cold, in-home activities may look a bit different, so take advantage of what you can only do in the winter. If you live in a snowy area, head outside with your winter wear on and have some fun! Build snowmen, have a snowball fight, sled, or just walk and enjoy the cold, fresh air. 


Visit Family for the Holidays 

The holiday season falls in early winter, and it’s the perfect time to see loved ones who are farther away. Pack up the car or hop on a plane with your family to spend the holidays with your relatives. The weather may be cold, but everyone’s hearts will be warm from long-awaited time together.



If you have family far away, head their way for the holiday season. You can even plan an extended vacation if time allows. Spending time with relatives makes for the perfect vacation because you make unforgettable memories with people you love – people you probably don’t see often enough! 


Even though the distance may be far, traveling to see loved ones is a worthwhile investment of time. The holiday season only comes once a year, and it’s even more special when you spend it with faraway family. 


Stay in a Mountain House 

If you’ve never stayed in an Airbnb, this winter is the time to do it! Through Airbnb, you can stay in someone’s home with your family while on vacation. This way, you save money that would otherwise be spent on a more expensive hotel. In addition, you can find an Airbnb in a unique location – like the top of a snow-covered mountain! 


Stunning handmade oil artwork of a landscape


Taking your family up to the mountains for a winter vacation is the perfect way to enjoy the snow and crisp, cold weather. You can look online for an Airbnb to stay at, book it a long time ahead, and then start planning adventures with your family in the surrounding area.

When you’re looking for a destination for your mountain house vacation, don’t be afraid to travel a bit! You can factor a road trip into this winter vacation idea as well. Driving up into the mountains in the winter never fails to provide beautiful views.


Tour a New City

When you’re looking for a new vacation destination, the winter weather often puts a damper on your plans. However, visiting a new city in the winter is always a great option! The cold weather may be a little nippy but walking through a new place with a light snow falling makes for a memorable winter vacation.


Heading on a winter vacation to the city requires some research. Get to know your city of choice before you get there, looking for the best restaurants, museums, and other attractions in the area. There are always great places to visit in every city – you just have to know where to look. 


Online, you’ll find helpful trip guides for whatever city you choose. Read restaurant reviews from locals and check out the websites for notable attractions around the city. This gives you a feel for what the place you’re visiting is like from the inside!


photos to art oil painting of elder white couple


Whatever you choose as your winter vacation destination, you’re bound to have a great time enjoying the cold (or warm) weather with your family. Take your time planning your trip and look through all the destination options at your disposal – there’s plenty of places to go! Talk things over with your family and get a feel for what everyone wants out of the winter vacation. This way everyone’s happy when you take off for your trip, And, of course, that’s what vacations are all about – sharing happiness with your family.