Make Your Next Trip Extraordinary

Travel Experts Share their Top 6 Tips for Successful Family Travel

by | February 14, 2024

The best family trips are fun and deeply rewarding. Successful family travel is about minimizing stress, smoothing out logistics, and keeping everyone in the family happy, from the grandparents to the teens and toddlers. A group of people with different ages, experiences, needs, and desires all traveling together makes for challenges, but when those challenges are overcome, it creates bonding moments and lifelong memories.

Family trips are more popular now than ever before. In 2019, the average number of travelers on a trip planned via The WOW List was three. Today, our groups average seven people. So during our 2024 WOW Week, Wendy, Brook, and Hannah (all moms themselves) had a live conversation and Q&A with several WOW Listers who are experienced family-travel planners as well as parents. Also joining us, to provide the grandparent’s perspective, was Brook’s mom, Susan Crandell. Watch the video below, and scroll down for the top takeaways from our conversation.

Shape global citizens

Wendy has been traveling with her two sons for 21 years, and they’ve been to 60 countries and counting. “Traveling gives your kids a confidence that will serve them well in life,” she said. Meeting people from completely different cultures and finding out you have a lot in common is deeply impactful. It’s how we create global citizens.

“When you model that being a traveler is part of your identity, your kids will pick up on that,” Brook said. In her family’s house, they have a hallway devoted to photographs that Zeke has taken on their trips; every time he walks to his room, he sees Egypt and Iceland and Vietnam and Norway and is reminded of the memories he made in each place. “He also has two world maps on the wall in his room, with pins for all the places he’s visited, the place he’s going next, and his dream destination,” said Brook.

Make friends

When Wendy’s sons were younger, they always brought a soccer ball on their trips. It’s a great connector, as tons of kids around the world love to play—and then you can leave it behind with the kids you meet. My own kids are still quite little, so I love making parent friends in playgrounds wherever we travel. It’s an ideal way to spend time with locals in the fresh air and get intel about more fun things to do with kids.

Wendy’s younger son, Doug, plays public pianos wherever he finds them—train stations, hotel lobbies, on the street, in music stores. It’s a fantastic ice breaker and conversation starter.

Assign jobs to kids

“Get buy-in from everybody, even if you’re the one paying the bill,” Susan suggested. In Iceland, she got her family to go horseback riding with her, something they wouldn’t have necessarily chosen—and then she went out of her comfort zone to ride an ATV, at her grandson’s request. It ended up being more fun than she expected. There’s always going to be compromise when traveling with a group, so it’s vital that everyone gets a say in the itinerary.

Zach Rabinor, on The WOW List for Mexico, took an eight-month road trip to 13 countries from Tierra del Fuego to Mexico with his family: his wife and two sons who were then 10 and 13, and at times joined by his in-laws and his mom, who was 78. His advice is to “involve everyone in the planning process, not just to avoid missteps but to get everyone engaged and excited.” Assigning responsibility to his kids helped them feel invested in the trip. One of his sons loves maps and took charge of directions. His other son, an avid reader, gave historical background and figured out the right tipping protocol in different places.

Seek out hands-on activities

Think beyond museums and landmarks. Brook and her family have “explored caves built by a pre-Viking civilization in Iceland, clambered through a Vietcong hideout in Saigon, and made cheese with a farmer in Norway—that last one wasn’t just hands-on, we were literally up to our elbows in whey!” These are the sorts of adventures that stick with all of us long after we’ve returned home, and the sort of experiences our WOW List fixers are experts at creating.

Jim Berkeley, on The WOW List for Egypt, gave his then-five-year-old son his camera in Luxor and let him follow his own inspiration. WOW List travel experts can also help steer you to guides who are excellent with children, or who even have their own children who might come along and play. “Let kids’ imaginations fly,” Jim says. “That’s what travel is all about—the world is their classroom.”

Schedule smartly

Jennifer Virgilio, one of our Trusted Travel Experts for France, England, Italy, and Switzerland, said that it’s going to be an incredibly busy summer in Europe. The Paris Olympics, Taylor Swift concerts, Wimbledon, the French Open, the Champions League, and the Formula 1 races are just the beginning of events taking over European cities. “It changes the whole landscape as a destination,” Jennifer explained. “If you are going to Paris for the first time, it’s best to wait.” If your heart is set on France and you can travel only in summertime, there are many lesser-known locales outside Paris that won’t be affected by the Olympics.

But even if, like many families, you’re forced to work around school breaks, there are alternatives to going in summer. For example, Thanksgiving is not a holiday outside the U.S., so it’s a smart time to head to Europe. If you must travel in summer, think about unexpected places such as Canada’s Maritime Provinces, including Newfoundland, to escape summertime heat, or Mexico’s Riviera Maya, to swim with whale sharks. Our WOW List experts can help you around crowds and maximize value wherever you go.

Keep it simple

Meg Austin, our expert for Caribbean beach vacations and ski vacations in the U.S. Rockies, highly recommends choosing direct flights whenever possible. Anything you can do to reduce hassle and smooth out logistics is worth the expense. “Don’t overschedule,” she urged. Make sure to build downtime into your itinerary.

All-inclusives are raising the bar on quality food—some even hiring Michelin-starred chefs, Meg reported. Ski resorts are great options for families, and ski resorts in the summer offer fantastic value, with plenty to do.

Pace your itinerary properly as well. “You don’t know how jet lag is going to affect your family,” said Jennifer. Try to stay awake the day you arrive and get to sleep at the time where you are.” Skip ambitious activities for the first morning, to give your group time to decompress after a long journey. Or skip jet lag all-together by traveling to the Caribbean, Mexico, or Central or South America.

Some final words of wisdom from Meg: “Always pack your sense of humor and your patience.”


We’ve published many stories about how to make the most of family travel over the years. Here are some of our favorites—and most helpful:

Traveling with Grandkids: Tips for a Successful Three-Generation Trip

This Is One Way My Family Gets to Know Locals When We Travel

How to Make Friends With Local People When Traveling

Colombia Is for Families: It’s Close, Safe, and Fascinating

Wendy’s Family Trip to Belize: Photos from the Beach and Sea

European Cities that are Surprisingly Kid-Friendly

We’re Just Back: Brook’s Family Trip to Egypt

Do’s and Don’ts for Your Trip to London

5 Ways To Get Your Child to Try New Foods When Traveling: A 12-Year-Old’s Advice

How to Make Sophisticated Travel Destinations Fun for the Whole Family

We Had the Best Family Trip in Whistler and We Never Put on Skis

Wendy’s Trip Photos from Morocco: An Unusual Spring Break Idea

My Family’s Best Christmas Abroad

How to Find the Perfect Vacation Rental: Tips for Your First Time, or any Time

Summer Vacation at a Ski Resort? Yes, and Here’s Why

Adventurous, Exotic Travel with Young Kids: It Is Possible

Italy Vacation Ideas for Every Age

Great Inspiration for Graduation Trips

We’re Just Back: Brook’s Family Trip to Southeast Asia

This Is What Makes Namibia So Cool

How to Have a Kid-Friendly River Cruise: Advice From a 12-Year-Old

Things to Know Before Booking Your Family Cruise: Tips From a 12-Year-Old

Why My Most Relaxing Vacation Was a Disney Cruise


Be a smarter traveler: Sign up for Wendy’s weekly newsletter to stay in the know. Read real travelers’ reviews, then use the black CONTACT buttons on Wendy’s WOW List to reach out to the right local fixer for your trip.

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