How To Plan a Winter Trip for the Whole Family

Winter travel is one of those highly anticipated vacations right when you need it most. You can get away after the holidays and catch up with extended family and friends or reconnect with the family unit. All you need is a destination and space that can accommodate your whole family.

Finding the perfect destination may vary by group, location and distance, but, at the end of the day, there are a few ways you can keep the whole clan together for a winter vacation.

Stay Flexible

The more flexible you can be about your family trip, including the destination and accommodations, the better. Cities may be a draw for a big group, what with the fun attractions for all ages by day and adult focus by night, but accommodations may be few and far between for larger groups. If you can, split up into hotels or find an Airbnb on the outskirts of town but with easy access to downtown so you can easily have the best of both worlds. To save on transportation hassle, consider a location within walking distance of local attractions, but in a big enough area that can host the whole family.

If your family stay isn’t really walkable, no problem — take advantage of rideshares, public transportation or rental cars and you can easily stick together or divide and conquer as you see fit.

Consider some rural options, like a scenic location with mild temperatures for nature-filled hikes and peace and quiet, or some off-beat destinations you’ve been meaning to visit, but haven’t had the chance. You can easily enjoy a new destination all together or visit an old favorite in a new way.

Consider the Weather

While narrowing down your destination options, consider the weather. While it’s merely a suggestion and not a guarantee, it will be helpful to know what you’re getting in for in a new destination this time of year. If you plan to drive, camp or spend time outside, make sure you’re prepared for the chance of snow.

One perk of the potentially bad weather, you’ll enjoy a good old-fashioned sleepover with family and friends by staying in — or indulge in all the winter activities you can outside. Either way, as long as you stay safe and smart regarding the weather in your given destination, you can plan ahead and work with the weather. 

Cousins at a family rental house on vacation © Oksix | Dreamstime.com

Be Open to a Quick Trip

With a big group, you have a mix of schedules and budgets. Not everyone is going to be able to take a full week or two or spend a whole paycheck on a trip. No matter how long the trip is, you can always beef it up with tours and activities. Check out local breweries and walking tours you can explore in your area and enjoy your destination like a local.

Consult the Gang

Start a group chat or email chain and see what the group is into. Yes, text groups are tough and a lot of ideas can get lost in translation, but laying out the plan and seeing what everyone is thinking can really narrow down the attendees, timeline and various plans you will need to make in advance of the trip. Be sure to meet at least once in person to discuss the details if the digital communication gets too confusing — not an option? Arrange a Skype call or Face Time with family representatives.  

Think Small

If it’s not a big occasion, don’t go overboard with plans. It doesn’t have to be the end all be all of vacations. It’s just a fun excuse to get your family post-holidays and catch up with those you’ve missed or slow down with the ones you rarely get the chance to.

You don’t have to fly to a destination for it to be a vacation. There are plenty of train routes, road trips and public transportation options that can take you to your destination just as easily as getting to an airport and hopping on a flight. The ride might be a bit longer, but you link up with the family and enjoy the ride together.

Seeking warmth? Head to a warm-weather city boasting fun activities for all ages and interests, including Miami, New Orleans, Austin, Charleston and San Diego. Depending on your home base, these cities are easily accessed by direct flight and come with a slew of all-season activities, enjoyed in small or large doses, depending on how much time you have.