Plan a Vacation that’s Fun for the Whole Family

Dan Weisman is dedicated to the pursuit of fun. From street food stalls in Beijing to tents at 12,000 feet in Wyoming, his travels have taken him around the world with family and friends. He believes that the keys to a successful trip are flexibility and communication. You can connect with him and other travelers on the FlipKey Blog.

As Christmas break draws near, family vacations are on many travelers’ minds. Getting together with the family means spending time with loved ones, but also seeing relatives who have varying ideas of fun. Uncle Ed may be perfectly happy hanging out on the couch and watching football all week, but the kids want to go swimming, and Grandma just wants everyone to spend time together. Whatever that means. How can you plan a family vacation where everyone has a great time? Here are a few pointers to get you on the path to a perfect vacation.

Choose an Easy Destination

The trick to choosing a destination for the whole family is finding one that no one can object to. There are a few factors that can make or break a destination: access, accommodations, and cost. These qualities can be balanced among family members in a number of ways to achieve equality. If you all have to travel roughly the same amount, then there should be no hard feelings off the bat. The best option is to pick a place that’s easy to get to, and easy to live in together. Helpful hint: it’s never easy for a family to live together in a single hotel room for more than one night, so find accommodations that fit the occasion.

The truth is, you can’t make everyone’s dream vacation come true in one trip. However, you can pick a place with enough options to make everyone happy. If it’s easy for everyone to reach your destination and relax, then you’re on the path to a great vacation.

Stay Together

In my experience, the best parts of a family vacation are the laid-back moments when everyone just hangs out together. I still remember family dinners I had as a little kid, and my Aunt never fails to remind us of the Scrabble games she won when my cousins and I were still learning to spell. These moments happen in between “activities,” and there’s no way to plan them. Instead, facilitate these times by staying together. Vacation rentals are a great solution to save money and get everyone under one roof. Renting a home is almost always less expensive than staying in a block of hotel rooms, and it gives your family space to spread out and relax together.

Or Split up and Have Fun

If you’re the one responsible for planning the family trip, try not to micromanage everyone’s schedules. Grandma may keep haranguing you to spend more time together as a family, but the truth is that your fun and Uncle Ed’s fun are different. (He’s never going to have fun at a museum, and you’re never going to have fun watching college football… and that’s OK!) Let the kids play in the pool all day, take a break with your spouse for a date night, let Uncle Ed watch football (and the kids). Outings with the whole crew can be great, but don’t feel like you need to be together every second of the trip. My favorite family vacations were the ones where I would wake up early every day to go water skiing, but you better believe that my brother wasn’t getting out of bed until the “early boat” came back and breakfast was winding down.

The best thing about getting the whole family together is having options for fun. Let the group know what the options are each day (or even at dinner the night before), and then split up and enjoy. Take advantage of the many adults who can share child-watching responsibilities, and don’t be afraid to say “no” to an activity that doesn’t fit with your idea of a great vacation. “Fun for the whole family” means there’s something for everyone: Go out and find it.

Rinse, Repeat

Anything can happen on a family vacation. If you do it right, then I can guarantee that at some point during your trip you’ll start planning the next one. Don’t panic! Families love spending time together, and great vacations are the foundation for memories that stay with you forever. When you do start planning the next trip, get the group together and check out this guide to the perfect family vacation. You’ll be on the path to family fun in no time.

For additional vacation ideas, check out FlipKey’s handy map (click to make it larger):

Perfect Family Vacation Map (FlipKey)

Featured Image: Family on a Ski Lift (

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