5 Ways to Make a Family Trip the Best Trip Ever


Who wants to go through the time and expense of planning a trip that no one enjoys? I suspect all of us can recall a moment on vacation when we thought, “This is not why I am here.” Time is our most precious resource. We use vacation for quality time with family, and as a way to recuperate from daily stress and create highlights that provide distinction from year to year. Vacations are important. Here are five ways to make them the best experiences possible for each family member.

Erynn Montgomery


Preparing yourself and your children before a holiday helps ensure a successful trip. Although it’s difficult to find time, there are several ways to make travel preparation fun, or even lucrative. Am I suggesting you bribe your kids? In a way, yes. Let me explain.

When my father-in-law’s children were young, he worked in Japan. Thanks to his efforts, connections and a few military perks, he was able to take the whole family on a series of trips to nearby countries and islands. Before these adventures, he would challenge the kids to learn as much as they could about their destinations. Then, he paid them for their knowledge! Everything they earned could be spent on local handicrafts, special treats or experiences during the trip. This incentive motivated his kids to write reports, learn foreign phrases and study maps. As a result, the kids felt invested in the trip and retained more from the experience.


Children love to feel like their opinions matter. Allow them to recommend destinations, ask them about the things that interest them most and then include an activity chosen by each family member. It’s a lot easier for an older child to support the desire of a younger sibling when they know they get a turn as well.

Erynn Montgomery


Turn everything you can into a game.

  • Taking a road trip? Put the names or initials of your children on one of the tires. When you stop for gas, the name closest to the pavement gets to pick a snack from the convenience store. Even older kids and parents love this game.
  • Order local cuisine and then vote on the best dish at every restaurant.
  • Find local games, like the Colombia Edition of Monopoly, for instance, or learn games like Pass the Pigs, Mexican Train or Bananagrams in Spanish.
  • Have a child snap an abstract photo and then divide into teams and try to find the place it was taken. This is especially helpful when passing time at an airport or waiting for food to arrive.
  • Collect something from each vacation, like a magnet, hotel keys, pressed flowers or (in our case) random rocks. I thought it was strange when my husband brought home a small rock from our Banff honeymoon. I now know this is a genetic predisposition; every one of our daughters likes to fill her pockets with rocks. They choose one small rock and bring it home. When we take time to admire the collection, they still remember the special places of their mementos. In a few cases, they’ve wanted to collect something rare or protected. Denying those requests has opened the door for deeper conversations about wilderness, culture and conservation.

Related: 5 Tips for Traveling With Children

Showing kindness

Above all others, kindness is the trait I hope to instill in my daughters. Travel has a way of condensing life lessons. I do not want them to be naïve or docile, or even sweet. No. Sweet people, especially women, can be taken advantage of. What I want is true compassion — for them to be mindful of others and to understand a wide range of life circumstances. I want them to barter fiercely for something, but leave a little more behind than what was agreed upon. I want them to see the beauty in different ways of life, compare it to the life they have and then create something new based on their own ideals. I want them to reach out to others and make a difference, and then allow people to reciprocate. The best way to learn kindness is by example. And when we are kind to ourselves, our traveling companions and strangers, the trip is better.

Preserving memories

Traveling with children provides a unique opportunity to shape the way they recall their childhood. They are more likely to remember things that occur away from the day-to-day of life. Time spent on vacation has a way of expanding in retrospect. Each day at the beach, on a hike or exploring a city can be recalled with special detail. We remember fun family meals from trips five year ago, but I often struggle to remember what we ate last week. These powerful, family-bonding memories can be brought even more vividly to mind through associated objects, tastes or images.

  • Age-appropriate journals: Verbal recall is difficult for young children; however, they can more easily draw pictures in their travel journals about how they perceive the world around them. Through art, they can capture memories and emotion. Drawings are powerful tools for older children and adults too. Allowing a few minutes of quiet reflection each day is a great way for everyone to appreciate and capture the day’s adventures. Here’s an example, created by Clement, the son of Tea Collection co-founder, Emily Meyer after their trip to Jaipur, India.
Elephant from Clement's Journal
Jaipur from Clement's Journal
Airplane from Clement's Journal
Play from Clement's Journal
  • Take photographs and video while traveling. If your destination is a place where your kids will interact with local children, pack a travel-size Polaroid. Depending on the location, some children may not have a photo of themselves. Seeing their expressions as the photos develop is priceless.
  • Children are most likely to remember a trip as being good or bad from beginning to end. Make a special effort to end with a highlight.
  • Talk about what you liked about each day. This will give children the opportunity to consider other perspectives and help them think more about what was important to them.
  • Buy one special souvenir from every trip or make necklaces out of international coins by drilling a very small hole near the top.
  • Upon return, tell your travel stories to others. Encourage them to make their own travel memories.
  • Throughout the year, look up the weather or news to see what’s happening in the places you loved.
  • Bring home a favorite recipe, and add it to your repertoire.
  • Keep contact with some of the people you met.
  • Print photos from the trip.
  • Keep working on those journals. Some of your most precious stories as parents will come from travel reflection.

Share your stories in the comments below or visit Tropic of Candycorn to help inspire others.

By Erynn Montgomery Guest Contributor Erynn Montgomery is the ringleader behindTropic of Candycorn, a website that encourages and inspires family travel. Before children, Erynn served as president and CEO of a humanitarian organization helping impoverished South American communities. As she and her husband awaited the arrival of their first child, they swore they would continue to travel—and that’s exactly what they’ve done, now with four daughters in tow.