Summer Is Here… Get Ready for Those Family Vacations! How to Depart with Less Drama and More Fun

 

Summer Is Here… Get Ready for Those Family Vacations!

How to Depart with Less Drama and More Fun 

By Laura Rahn, Family Travel Coach

Summer is officially here and family vacations are underway! The excitement is real…and so is the stress that can happen before departure day. As a certified family travel coach with Seldom A Dull Moment, based in Purcellville, I encourage families to remember that the vacation doesn’t start when you arrive at your destination. The vacation starts before you even leave the driveway.

As departure day approaches, the excitement for your family vacation reaches its peak. The lead-up to leaving is just as important as the dreaming and designing stages. Packing suitcases together, double-checking travel documents, and talking through the itinerary helps build anticipation and family unity. It’s also a chance to share expectations, excitement, and even anxieties before the adventure begins.

This pre-departure time sets the tone for the entire vacation and lays the foundation for memorable experiences and meaningful family moments.

Create a Family Countdown

The countdown to a family vacation is often one of the most exciting parts of the experience. Involving the whole family builds anticipation and strengthens togetherness long before the trip begins.

Create a vacation countdown chain or calendar together. Even something simple like “100 Days Until Vacation” can turn an ordinary week into part of the adventure. The shared excitement gives everyone something to look forward to and allows each family member to contribute ideas.

You can also create themed countdown activities:

Start a family playlist on Spotify or Pandora. Let older kids take ownership of building the playlist and encourage everyone to add songs connected to the destination or mood of the trip.

• Design a vacation Bingo card with restaurants, landmarks, activities, or animals you hope to see.
• Watch a movie connected to your destination.
• Cook a meal inspired by where you’re going.

The countdown itself becomes part of the vacation memories.

Make Packing a Family Affair

Packing for a family vacation can either become a stressful last-minute scramble or part of the excitement. Involving everyone in the process creates ownership and builds anticipation.

For younger children, choosing favorite outfits, toys, or travel games helps them feel invested in the trip. Older kids can take more responsibility by pre-packing themselves using a checklist:

• 5 outfits
• Pajamas
• Bathing suits
• One dressy outfit
• Walking shoes
• Toiletries

This gives older kids ownership over what they wear and helps reduce stress on departure day.

Packing cubes are another simple tool that can make a huge difference. They help maximize suitcase space and allow families to organize clothing by destination, activity, or family member.

A few additional packing tips:

• Pack favorite individually wrapped snacks, especially ones that may not be available at your destination.
• Clarify dress codes ahead of time. “Formal dinner” can mean very different things to different family members.
• Discuss footwear needs in advance. Will you need hiking shoes, beach sandals, or comfortable walking shoes?
• Encourage everyone to pack one fun item that makes them smile.

Ultimately, packing becomes more than preparing luggage. It becomes a tangible reminder that the family adventure is almost here.

Reflect on Your WHY

As you get closer to departure day, take time to revisit your family’s “why.”

Why are you taking this vacation in the first place?

In the rush of reservations, packing lists, and logistics, families sometimes forget the deeper purpose behind travel. Gathering together before the trip to revisit your intentions can help everyone feel more connected and emotionally prepared.

Consider asking:

• What are you most excited about?

• How do you hope to feel during this trip?

• What do you hope happens as a family?

• What personal experience are you hoping to have?

These conversations create opportunities for active listening and help family members feel heard before the vacation even begins. They also create space for anxieties or concerns to surface in a safe and supportive way.

Sometimes the most meaningful vacation planning conversation has nothing to do with the itinerary.

Set Expectations Before You Leave

One of the best ways to reduce family vacation conflict is to talk through expectations before departure day.

This is especially important when traveling with older kids or multigenerational groups. Creating shared expectations ahead of time gives everyone a sense of ownership and helps prevent misunderstandings during the trip.

Some important topics to discuss:

• What will screen time look like?

• Will there be alone time built into the vacation?

• Will every meal be together?

• Are there activities family members can opt out of?

• What balance of together time versus independent time feels right?

Teenagers and young adults may not want to spend every moment together, and that’s okay. Building flexibility into the itinerary often creates a more relaxed and enjoyable experience for everyone.

When families have these conversations before leaving home, they are much less likely to have heated discussions while away. Everyone understands the expectations and feels like their needs matter.

Bring Home the Memories

Don’t forget the souvenirs!

Bringing home ornaments, magnets, stickers, postcards, or small keepsakes gives families tangible reminders of shared experiences. These items often become conversation starters that allow families to relive favorite memories long after the vacation ends.

These simple items become visual reminders of connection, adventure, and time spent together. Reflecting on the vacation after returning home also strengthens family bonds. Looking through photos, sharing favorite moments, and remembering funny mishaps helps extend the joy of the trip well beyond the final day.

When families work together before departure, vacations begin with excitement instead of exhaustion. The memories start long before you reach your destination..

 Remember, the goal isn’t a perfect vacation.
It’s less drama and more fun.

The Best Family Vacations Begin Around the Table

*This blog post was featured in the March, 2026 issue of Purcellville Living magazine as a featured story and is shared in it's entirety below.

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.

Let’s connect!

• LDRAHN@comcast.net 
• laurarahn_travelcoach
• seldomadullmoment.etsy.com
• www.seldomadullmoment.com
• Purcellville, VA

Resources referenced:

• Talker Research surveyed 2,000 American parents of school-aged children (aged 6–17); the survey was commissioned by Visit Anaheim and administered and conducted online by Talker Research between April 7–15, 2025.
• https://stories.hilton.com/2026-trends