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My Favorite Ways to Have More Fun Together on Vacation.

Sep 5 2026 | By: Jackie Stringham Travels

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Fun has less to do with creating an impressive itinerary and more to do with how we experience it together.

We often plan family vacations around where we’ll go and what we’ll see. But when the trip is over, the moments we remember most aren’t always the famous attractions.

We remember the ridiculous car games. The afternoon everyone jumped into the pool. The dessert we ordered twice. The inside joke that made no sense to anyone outside our family.

Here are my favorite ways to bring more play, laughter, and shared joy to a family vacation.

 

Luxury travel planning support for families who want a smoother, more enjoyable vacation experience.

A thoughtful itinerary can turn a good getaway into a genuinely enjoyable family experience.

 

1. Let Everyone Choose One Adventure

A trip becomes more fun when everyone gets to influence it.

Before you leave, ask each family member to choose one vacation activity. Set any necessary limits—such as budget, distance, or available time—then give each person the chance to contribute.

One child might choose mini golf while another wants to visit an aquarium. An adult may request a scenic hike or a slow breakfast at a local café.

Part of the fun is seeing the destination through someone else’s interests. When it’s your turn to participate in another person’s choice, join in with enthusiasm. The activity might surprise you.

2. Create a Family Vacation Challenge

A friendly challenge can turn an ordinary day into a shared game.

Make a list of things to find, try, or photograph during the trip. Choose challenges that fit your destination, such as:

  • Find the funniest souvenir

  • Try a food you’ve never eaten

  • Spot something in every color of the rainbow

  • Learn three facts about the place you’re visiting

  • Take a photograph that makes everyone laugh

  • Find the best local dessert

  • Count how many different animals you see

Keep the competition lighthearted. You can work as one team, divide into pairs, or let everyone complete the list at their own pace.

The real prize is having a collection of funny moments to talk about afterward.

3. Give Ordinary Moments a Playful Twist

Not every fun memory needs to come from a planned attraction.

Turn the walk back to your hotel into a game of “Would You Rather?” Let the kids rate each day’s dessert. Invent silly awards, such as Best Vacation Hair, Most Unexpected Snack, or Person Most Likely to Fall Asleep in the Car.

Long lines can become opportunities for storytelling games. Road trips can include themed playlists, trivia, or a search for the most unusual roadside sign.

A little imagination can transform the slower parts of travel into some of the best parts.

4. Say Yes to Something Unexpected

Some of the happiest vacation moments begin with an unplanned suggestion.

Stop when someone notices an interesting shop. Dance to the music of a street performer. Take the scenic route. Order the strange-looking pastry. Let the children get wet in the fountain if you have dry clothes nearby.

You don’t have to abandon your plans entirely. Simply leave enough flexibility to follow a little curiosity.

Fun often appears when we stop trying to manage every minute and allow the day to surprise us.

5. Bring One Easy Family Game

Pack something everyone can enjoy without much setup: a deck of cards, travel-sized board game, conversation cards, or a small set of dice.

Games are perfect for rainy afternoons, restaurant waits, airport delays, and quiet evenings. They give everyone a reason to gather without needing to plan another outing.

You can also invent a game specifically for the trip. Ask everyone to predict what will happen that day, hold a family trivia contest, or vote on categories such as Best Meal, Funniest Moment, and Biggest Surprise.

Choose something simple enough that playing never feels like work.

6. Try Something New as a Family

New experiences naturally bring out playfulness. Everyone is learning, making mistakes, and discovering what they can do.

Take a cooking class, try paddleboarding, sing karaoke, learn a local dance, ride public transportation somewhere unfamiliar, or order a dish to share that no one has tried before.

It doesn’t matter whether anyone is especially good at the activity. In fact, being beginners together is often what makes it memorable.

The goal isn’t to perform well. It’s to collect a story your family will enjoy telling.

7. Let the Kids Be the Tour Guides

Give the children an opportunity to lead part of the day.

Depending on their ages, they might navigate to the next stop, choose where to eat, read facts about an attraction, or give everyone a “tour” based on what they’ve learned. Younger children can decide which direction to explore or select the next animal to find at the zoo.

Leadership turns sightseeing into participation. It also gives adults a chance to relax and see what captures the children’s attention.

Their version of a tour may not be entirely accurate, but it will probably be entertaining.

8. Make Time for Unstructured Play

It’s tempting to fill a vacation with experiences you can’t have at home. But children often have the most fun when they are free to play without an agenda.

Leave room for swimming, building in the sand, exploring a park, tossing a ball, or inventing games in the hotel room. Join them sometimes instead of watching from the side.

Get in the pool. Build the sandcastle. Race to the next tree. Agree to be the customer at the pretend restaurant.

Children remember when adults enter their world—and adults often have more fun when we give ourselves permission to play.

9. Use Photos to Make Each Other Laugh

Vacation photos don’t all need to be beautifully posed.

Re-create an old family picture. Take turns inventing dramatic poses. Photograph everyone’s reaction to trying a new food. Let each person direct one silly group photo.

You can also hold a daily photo contest with categories such as Funniest, Most Creative, Best Action Shot, or Picture That Best Captures the Day.

These images may never appear in a frame, but they’ll bring the personality of the trip rushing back.

10. Repeat What Everyone Loves

There’s no rule that says every vacation day has to offer something new.

If everyone loved the taco stand, go back. If the hotel pool was the highlight of the day, make time for it again. If a simple card game had everyone laughing, play another round tomorrow night.

Adults sometimes feel pressure to maximize a trip by constantly moving on to the next experience. But repetition can become a tradition—and traditions are part of what makes family travel special.

11. Protect Everyone’s Energy

It’s difficult to have fun when everyone is hungry, exhausted, or overstimulated.

Pack snacks. Take breaks. Avoid scheduling every hour. Pay attention when enthusiasm starts turning into irritability, and be willing to change the plan.

Rest and fun aren’t opposites. A slow afternoon can give everyone enough energy to enjoy the evening. An early bedtime may make tomorrow’s adventure much happier.

Sometimes the best way to create more fun is to know when everyone has had enough.

12. End Each Day on a Happy Note

Before bed, ask everyone to share the funniest moment of the day. You might also name something another family member did that made the day more enjoyable.

This simple ritual brings everyone back together, even if the day included disagreements or disappointments. It reminds you that a vacation doesn’t have to be perfect to contain something wonderful.

Write the answers in a notebook or save them in your phone. By the end of the trip, you’ll have a collection of memories told in your family’s own words.

Fun Is Something You Create Together

The best family vacation moments rarely depend on everything going according to plan.

They happen when someone makes a terrible joke in the car. When everyone tries something unfamiliar. When the adults put aside their schedules and join the game. When a wrong turn becomes an adventure instead of a problem.

Choose experiences your family can share, but leave room for silliness and surprise. Follow one another’s curiosity. Repeat the things that make everyone happy.

You may discover that the most fun part of your vacation isn’t what you do—it’s the way you enjoy doing it together.

 

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