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How to Plan a Family-friendly Vacation this Winter

How to Plan a Family-friendly Vacation this Winter

When people think of vacationing in the winter, they usually think of luxurious tropical islands with majestic blue waters and palm trees. Some, on the other hand, would rather sip hot chocolate as they rest after skiing in the Alps.

Family-friendly can be anything from a relaxing spa resort to a luxury hotel with a suite and a kitchenette. For many families, staying at an all-inclusive resort with kids is ideal because it means that they have one less thing to worry about while on vacation!

Table of Contents

  1. What’s the best family vacation planning tip?
  2. What activities does your family enjoy?
  3. What are some family travel destinations to consider?
  4. How can you keep everyone happy?
  5. What to bring with you on a family vacation?
  6. What should be on your family vacation checklist?
  7. What are the best apps to use for travel?
  8. Should I get travel insurance?
  9. Conclusion

So, what makes a family-friendly vacation, and how do you plan for one?

When coming up with a list, try to think about features that would make a vacation family-friendly. Having activities that are easy to access, affordable, and close by all counts!

The best way to plan for a family winter vacation is to start by doing some research. Check out and to see what's available in your price range and what cities/destinations are most family-friendly.

Family Vacation Planning Tips

As the winter months approach, so does the cold weather.

For some families, this is a perfect time to head out and go on a family-friendly vacation. Family vacations can be daunting when it comes to planning because you want to make sure that everyone in your group (humans and pets) is happy and satisfied with their experience.

Family Vacation Planning Tips

To help you plan for your upcoming winter break getaway, here's what to consider when planning a family-oriented vacation; some ideas of places to consider visiting; and how to keep everyone in your family or group happy while traveling. 

Here are some questions to ask as you plan for your trip:

1. What Activities Does Your Family Enjoy?

Before booking anything, take about an hour–or even better, a weekend–to sit down and jot down a variety of activities for family fun. Some questions you may want to ask yourself include:

activities that your family enjoys

  • Do we enjoy hiking? Or, would they like a bike ride more?
  • Would my children enjoy traveling through a historic city?
  • Would my spouse love an outdoor adventure? 

This doesn't have to be an intense exercise–in fact, majoring in minutiae can miss the larger picture–but jotting down some of your family members' favorite activities might help you get more specific once you start researching destinations. 

And don't forget about pets! If your dog would enjoy dozing on the beach for two weeks, then Hawaii is calling your name–it's one of six places that are designated as "dog friendly."

2. Family Travel Destinations

Family Travel Destinations

If you're considering staying in the US then perhaps some of these ideas will give you some inspiration:

  • Consider heading to Florida for a winter break--it's warm, on the water, and has plenty of outdoor activities for children. Plus, Disney World is only about three hours away!

  • Family cruises are always an option–you don't have to fly or rent a car so it can save some money, plus kids love the idea of living on a boat for several days (and who doesn't love sleeping in late while taking in some sun?) Keep your eyes out for bargains during this off-season, too!

  • Family-friendly activities abound in Florida: Disney World is just one of many options (and yes, it's always open). If your family enjoys theme parks, you can consider Universal Studios or Busch Gardens while staying within driving distance.

However, it’s important to remember that when spending time under the sun, you should always wear sun protection. Whether it’s sunscreen, sun hat, and a combination of both, you should always have it handy! 

For sun hats for the whole family, you can visit the GearTOP shop for high-performing sun hats that has a wide brim and feature the highest level of sun protection from fabric - UPF 50+

  • If you prefer skiing or snowboarding, try heading to the Poconos, Vermont, or even the Catskills. Family resorts abound in these parts, and there's no better time than winter to go! 

New Jersey claims that they have "the largest ski area [in] the state," so this might be an excellent option for you if you want to stay relatively close to home and explore a new place. 

Staying protected for winter weather adventures is just as important! For affordable gear that doesn’t compromise quality, GearTOP’s got you covered during the cold weather

3. How Can You Keep Everyone Happy?

Now keep in mind that everyone has different interests. Your idea of the perfect family vacation might be different from your husband’s or your parents.

Keep Everyone Happy

Consider these ideas as you plan:

  • Family-friendly dinners (buffets, casual) 
  • Family activities (especially those not involving screens or electronics!)
  • Family board games and other fun diversions
  • Family friends who live in the area (bring them along too if they'd enjoy a mini-vacation!)

4. What to Bring With You on a Family Vacation?

Some essentials to consider packing include:

Sunscreen, hats and sunglasses, comfortable traveling clothes/shoes/accessories, water bottles to refill, snacks for everyone including pets! If there are items that you use frequently so consider packing them (and double-check that they were not left in the last hotel room you stayed in).

Vacation essentials

Depending on where you’re headed, whether it’s a sunny outdoor location to get away from the cold, or an icy wonderland to enjoy it, you should have the right gear with you to ensure that you’re fully protected from the elements.

If you’re looking for affordable yet high-quality gear for both sunny and icy spots, you can check out GearTOP’s shop for their complete collection. Visit their shop today by clicking the link below!

5. What should be on your Family Vacation Checklist?

Family Vacation Checklist

Even if you're just going away for a weekend or even for an entire week, it's always smart to have an itinerary in mind. Your family vacation checklist should include:

  • Family passports, visas, and other travel information
  • Family cell phones/chargers with international adapters or SIM cards if needed! It will be more convenient to be able to text each other about restaurant recommendations without paying expensive fees.
  • Family boarding passes luggage tags, cash/credit cards/ATM cards/travel checks

Make Use of Family Travel Insurance and Family Travel Apps

To make planning and logistics easy, you can turn to technology. With a swipe of your smartphone, you can look up awesome restaurant recommendations in an instant, get a ride, and book a hotel at the last minute!

 Family Travel Insurance and Family Travel Apps

A few apps we love include:

  • Trip It. This app makes it easy to keep all your travel plans organized in one place, so you don't have to worry about forgetting anything once you get on the road or lose that scrap of paper that had your flight info on it!

This app makes it easy to keep all your travel plans organized in one place, so you don't have to worry about forgetting anything once you get on the road or lose that scrap of paper that had your flight info on it! 

  • Uber & Lyft. These apps make it easy to get around your destination without having to rely on public transportation, plus they're often more affordable than a traditional taxi service!

  • Hotel Tonight. This app allows you to book last-minute hotel rooms for up to 50% off the standard rate. It is perfect if your family trip plans change or you just want a vacation getaway at the spur of the moment!

Should I get family travel insurance?

Family travel insurance is something we highly recommend thinking about before booking any vacations with your kids. You never know when an accident might happen! So, it's worth protecting yourself and your family in advance!

family travel insurance

Family travel insurance is a great idea if you're going to be flying, taking a cruise, or participating in any activities that require physical exertion. 

Don't forget the all-important trip cancellation and trip delay protection, too! No one wants their vacation ruined by an unexpected storm. So, it's worth getting coverage for this kind of thing before checking out!


Whether you are planning a vacation to escape the winter or stay local, your family must have an enjoyable time. 

But, no matter how much fun you and your family is having, outdoor protection should never be put in the backburner. No matter where you’re spending your winter vacation you should always have the right gear. This is where GearTOP can help you out! 

Have your pick between affordable yet high-quality outdoor gear for any season! Whether you are off to a winter wonderland with the whole clan or to a sunny paradise, have top-notch protection from the elements. 

With products ranging fromversatile balaclavas,sweat-wicking beanies,gloves for cold wear, andwide brim sun hats and visors for more summery destinations, you can trust GearTOP to deliver reliable protection no matter where you're heading. Visit the GearTOP shop today! 

We hope this blog post has given you some ideas on how to plan your winter vacation. 

Do you have any additional questions about the information in this blog post? Let us know in the comments section below!

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