(Away From) Home For the Holidays: How to Plan a Multi-Gen Holiday Getaway Without the Stress
The holidays are meant to bring families together, whether you celebrate Christmas, Hanukkah, Kwanzaa, or simply the end of the year. But let’s be honest: sometimes the magic of the season gets overshadowed by the chaos of hosting, the tension of clashing personalities, and the overwhelm of trying to make everyone happy.
That’s why a holiday vacation might be the best gift you give your family this year. Here’s how to plan a multi-generational holiday getaway that brings more connection and less stress—no burnt casseroles or crowded guest rooms required.
Step 1: Set the Scene — Sun or Snow?
Before you start stressing about flights, gifts, and packing lists, take a deep breath and ask yourself one simple question: Sun or snow? Do you dream of swapping your sweaters for swimsuits and heading to a tropical escape, or would your family rather cozy up in a winter wonderland surrounded by twinkling lights?
This first choice sets the tone for your entire holiday trip. Some of my favorite multi-generational picks include sunny getaways like Mexico, Caribbean cruises, or Hawaii. If you’re still dreaming of a snowy escape for the holidays, Colorado, Quebec City, Northern Italy, or the Alps make for a perfect winter retreat.
Step 2: Find Your Family’s Perfect Space
Once you’ve chosen your destination, it’s time to think about where—and how—your family will stay. Holiday travel can be stressful, so be honest about what helps everyone travel happily together. Think: does your crew thrive under one roof in a spacious villa, or do certain family members need their own space (and a little quiet)?
Maybe you’ve got early risers, light sleepers, or teens who value privacy. Choosing separate wings of a resort or connecting rooms can make all the difference. The good news? Many resorts now offer family suites and adjoining options that give you both togetherness and plenty of breathing room.
Step 3: Let Everyone Pick Their Must-Do
If you’ve ever tried to please everyone on a family trip, you know it’s the fastest way to lose your holiday spirit. Instead of juggling a million opinions, try this simple trick: let each person (or each family group) choose one priority for the trip. Maybe Grandpa wants a round of golf, Aunt Sarah’s dreaming of a spa day, the kids can’t wait to build a snowman or meet Santa, and you’re craving one relaxed, picture-perfect family dinner.
Once everyone’s had their say, build your itinerary around those pillars. It keeps things fair, focused, and fun so no one feels left out, and you can finally skip the “but I wanted to do this!” drama.
Step 4: Embrace a Little Space
It’s easy to feel like every single minute of a family vacation should be spent together, but sometimes, the best memories come from a little breathing room.
Give yourself (and everyone else) permission to do things separately. Maybe Grandma wants to take a nap while others explore, or your teens would rather hang back while you take the little ones to a local attraction. That’s okay! Building in “free blocks” of unstructured time lets everyone relax and recharge. The result? Fewer meltdowns, more laughter, and a happier, more relaxed version of the family time that you’ve been dreaming about.
Step 5: Bring Your Holiday Traditions With You
Leaving home doesn’t mean you need to leave behind your holiday spirit! In fact, bringing a few of your favorite traditions along can make your trip even more meaningful. Bake cookies in your villa’s kitchen, light the menorah together, read a holiday story on Christmas Eve, or sip cocoa in matching pajamas while you watch your go-to holiday movie (I prefer [Kate—put Christina’s favorite holiday movie here if you know it; if not, I’ll ask!], myself). If you’re feeling even more adventurous, holiday travel is the perfect excuse to get creative with the space around you: start a snowball fight, decorate your space with handmade holiday decor, or exchange gifts on the balcony instead of under the tree!
With a little intention, those familiar moments blend beautifully with your new surroundings, creating traditions that grow right alongside your family.
Step 6: Call in Reinforcements — Use a Travel Advisor
Planning a trip for multiple generations can feel like herding reindeer: adorable, but chaotic. Between different budgets, personalities, and priorities, it’s easy to feel like planning the perfect getaway is more of a headache than a holiday.
That’s where a travel advisor comes in. We act as your built-in peacekeeper, presenting options that balance everyone’s needs, handling group logistics like flights and dining, and keeping strong opinions from derailing your holiday cheer.
Best of all, we genuinely love doing it! Crafting a trip that makes every member of your family happy—from Grandpa to the littles—is our favorite kind of magic.
Step 7: Keep the Joy in the Journey
A little preparation goes a long way toward keeping your holiday trip joyful instead of stressful. Book early, especially if you’re eyeing villas or larger suites, since they disappear fast. Set expectations before you go: Will there be gifts? How will you handle splitting costs or early excursions? Create a group chat to share updates (and maybe a few funny memes when planning gets intense).
And most importantly: stay flexible! Weather, moods, and travel delays happen—but if you keep your focus on connection instead of perfection, your holiday getaway will be everything it’s meant to be: time well-spent, together.
Planning holiday travel with grandparents, kids, cousins, and everyone in between isn’t easy, but it can be incredibly meaningful. You may just discover that the best way to be together this season… is to get away.
And we’d love to help you make it happen.
Who is Christina?
Meet Christina Vieira, a Traveler, a Planner, and a Mom. She is also the owner of Showcase the World Travel, a modern travel agency that helps busy Moms take the vacation they deserve without adding “planning it all” to their to-do lists. After all, Mom should get to enjoy their vacation too.
She specializes in Disney, the Caribbean, Europe, and has helped dozens of families have magical vacations that they will always remember. She loves traveling with her four-year-old, Annabelle. Her favorite destinations include Walt Disney World, Wyoming, and Prague.
