Monday, March 2, 2026

The Best Family Vacations Begin Around the Table


Why listening matters more than the itinerary

“I need a vacation from our vacation!”

“We spent all this money, and you’re acting like this?”

“This is so boring, why do I have to do this?”

“I just want to talk to my friends, and check Tik-Tok!”

I think we’ve all been there. Hearing those words, spoken by you or your child, while on a family vacation can bring stress and anxiety to the surface, especially when you’re away from home.

Family vacations are meant to be a break from everyday life, yet they often come with big expectations, strong emotions, and plenty of moving parts. Travel has the power to impact each family member individually, connect generations, and create lasting memories, and only when everyone feels connected and supported along the way.

The good news? It all starts before you even leave the house.

Asking thoughtful questions, practicing active listening, and building in flexibility and compromise are key to planning your next great family vacation. These simple habits can help transform the planning process, and the trip itself, into something everyone feels good about.

As a certified family travel coach and former educator, I help families slow down, talk things through, and design vacations that reflect who they are and what they need. When families understand why they’re traveling, and how they want to feel along the way, they’re far more likely to create experiences everyone enjoys and feels ownership of.

And it all begins with one simple step: asking the right questions.



Asking Questions

Before getting into the thick of planning a family vacation, it’s important to dream about it first. Give each family member the opportunity to share their hopes for the trip. Include all voices, and really listen to what each person is saying.

It begins with intentional communication as a family and bringing all travelers (yes, including kids) to the table to “dream” about the upcoming vacation. Some questions you might ask each person, even young children (I’ve done this with eight-year-olds, and it works!) include:

  • Why do you want to go on this vacation?

  • What is one thing you hope to do on this trip?

  • How do you want to feel when you get home? What do you hope to tell your friends about this vacation?

  • If you could go anywhere on vacation, where would you want to go?

Prior to getting into the thick of planning a family vacation, it’s important to dream about it. Let each family member share their hopes and dreams about this vacation. Include all voices and listen to what each person is saying.


When every family member is invited to dream, the vacation begins with connection, long before the bags are packed.

Active Listening

As each adult or child shares their responses, it’s important to practice active listening without judgment. Encourage everyone not to interrupt the speaker and to focus fully on what is being said. When you actively listen, you validate the person speaking, and they feel that their thoughts and ideas matter.

Through sharing and listening, families can begin to create a shared vision of the vacation before it even begins.


Compromise and Flexibility

Now that everyone has shared their hopes and dreams for the upcoming vacation, it’s time to begin designing it together. A family vacation is an opportunity to come together, and when all family members are invited to give input, each person gains a sense of ownership in the experience.

Asking each family member what they want to do allows everyone to hear,  and understand the desires of each traveler. It also introduces the idea of compromise before you ever leave the house.

Understanding that the vacation will include “what you want," and  “what your brother wants,” opens the door to meaningful conversations about flexibility and compromise, helping ensure that everyone has something on the trip they’re genuinely excited about.

The most successful family vacations leave room for flexibility, compromise, and something everyone can look forward to.


At the heart of my coaching philosophy is the importance of connection. Whether it’s a family trip or a solo adventure, travel creates bonds that last a lifetime. Traveling with someone you love can redefine family connections, and bring that feeling of home to wherever you are.

Travel has the power to transform lives, foster connections, and create cherished memories. My approach as a family travel coach highlights the importance of understanding the motivations behind travel. As families navigate new stages in life, embracing the adventure of travel can lead to personal growth and lasting bonds. 


Whether you’re planning a family vacation or a solo journey, remember that every trip is an opportunity to explore not just new places, but also develop new connections with  parts of yourself and your family.  It all starts at the table, before even leaving the house.