Family Travel Tips: How to Keep Everyone Happy

Planning a family vacation is exciting—but let’s be honest, it’s not always easy. One person wants adventure, another wants to relax, and someone always forgets their charger. Whether you're traveling with little ones, tweens, or teens, the ultimate goal is the same: making sure everyone feels included, relaxed, and ready for fun.

Family enjoying a beach vacation

If you’re already thinking this sounds familiar, you might also love my Family Vacation Planning Guide—a downloadable resource to help you plan ahead and avoid those last-minute stressors!

As a travel advisor who works with busy families, I design trips that are personalized, well-paced, and thoughtfully planned—so every traveler (yes, even the hard-to-please teen) ends the trip with a smile. If you're dreaming of a summer vacation that's equal parts indulgent and low-stress, here are my favorite tips for keeping everyone happy.

Choose Accommodations That Actually Work for Families

The perfect hotel room with room for the family

Luxury travel doesn’t always mean one giant suite—and it doesn’t have to. Whether it’s a connecting set of rooms in Paris, a beachfront villa in Greece, or a family-friendly resort in Portugal, the right accommodations can give everyone space to rest and recharge.

What I recommend:

  • Villas or suites with kitchens and common areas

  • Resorts with family-specific perks (like kids’ clubs, family pools, and babysitting)

  • Multiple rooms or adjoining spaces with private entrances

I help my clients choose accommodations that match their family’s travel style—not just what looks pretty in photos.

Set the Right Pace—And Plan for Downtime

A hands-on activity during a museum tour

The biggest mistake I see families make? Trying to do too much. While it’s tempting to see all the sights, the best memories often come from unhurried meals, spontaneous moments, and time to breathe.

My tip: Build in a balance of structured activities and free time.

  • Schedule private tours in the morning, and leave afternoons open.

  • Pick hotels with pools or walkable neighborhoods for easy downtime.

  • Let each family member choose one “must-do” experience.

Add Activities That Spark Everyone’s Interests

Adding a bike tour can be a great way to keep active and keep the kids happy!

Every family has a mix of personalities. Your daughter wants history, your son wants animals, your spouse wants wine tastings… and you want peace. The good news is, with the right planning, everyone can have their moment.

What works well:

  • Private cooking classes, biking tours, or market visits

  • Behind-the-scenes museum tours with family-friendly guides

  • Adventures like ziplining, kayaking, or gondola rides

When we work together, I get to know your family and recommend custom activities to match your interests—so no one is left out.

Let Someone Else Handle the Logistics

A family waiting to board a train for their next destination!

Coordinating transportation, hotels, activities, dinner reservations, and downtime… it’s a lot. And if you're the "planner" in the family, you know how quickly that mental load adds up.

Luxury travel means having support, and that’s where I come in.

When we work together, I:

  • Coordinate flights, transfers, rail, and ferries

  • Book hotels and resorts that fit your needs

  • Organize private tours and day trips

  • Provide a detailed, personalized itinerary you can access on the go

  • Offer support before and during your trip if anything unexpected pops up

✨ All you have to do is show up and enjoy.

Give Everyone Something to Look Forward To

A family enjoying a beach day

Kids love a countdown. Teens love independence. Adults love wine tastings and beautiful views. Including moments that feel special for each traveler helps make the trip memorable—and gives you all something to talk about long after you return home.

Whether it’s a sunrise hot air balloon ride, a chocolate workshop in Switzerland, or simply a night off with a private babysitter, the little touches go a long way.

Ready to Plan a Trip Everyone Will Love?

Ready to head on their next adventure!

You don’t need to be the expert. That’s what I’m here for.

As your travel advisor, I’ll help you choose the right destination, take care of all the moving pieces, and design a family vacation that feels effortless, exciting, and 100% personalized.

📅 Click here to schedule your custom vacation consultation

Let’s make this summer your family’s best yet.

Laura Legg

Hello, I’m Laura, the proud owner of Castaway Destinations, a boutique, full-service travel agency. As a busy mom of three, I understand the challenges of planning the perfect vacation. My dedicated team and I specialize in creating bespoke luxury trips across Europe and the Caribbean.

We leverage our extensive travel experience and destination knowledge to provide exceptional, personalized service tailored to your unique needs. Together, we make travel seamless and stress-free. Let’s turn your dream trip into a reality!

Next
Next

Where to Go Instead: Crowd-Free Alternatives to Popular Summer Destinations