The Great Holiday Escape: Why Going Away Works

How to Make Holiday Travel Unforgettable

by Tiffany Figueiredo

Last December, one family came to us ready to trade stress for something entirely different.

Instead of coordinating multiple households and juggling gift exchanges, they spent Christmas on safari in the Sabi Sands and Zimbabwe, then rang in the new year in Cape Town. There were game drives at dawn, evenings under African skies, and carefree beach days along our favorite stretch of sand. It felt less like a break from tradition and more like the start of a new one. It was a perfectly timed escape from their busy lives, and precisely why more families are rethinking their holiday traditions.

What made their experience so transformative? Here’s what we've learned about holiday travel: doing it well requires an entirely different mindset than your typical summer getaway. What separates a holiday you remember fondly from one that leaves you longing for home is knowing what you’re really signing up for.

The Great Holiday Escape: Why Going Away Works

There is something revolutionary about removing your family from the familiar backdrop of holiday expectations. At home, everyone slips into their assigned roles: Mom orchestrates, Dad carves the turkey, teenage cousins disappear into their phones. Place those same people in a Moroccan riad or a Swiss chalet, and suddenly the script gets rewritten.

When the logistics are handled by someone else, families remember what they actually enjoy about being together. The magic is not just in the destination but in the permission to be different. Away from home, no one expects the dining room table to look like a magazine spread or the gift exchange to follow the family protocol established in 1987.

This approach works particularly well for families in transition, such as empty nesters adjusting to smaller gatherings, divorced parents creating new traditions, or multigenerational groups trying to please everyone.

Rewriting the Holiday Script

The hardest part about spending holidays abroad is not the logistics. It’s giving yourself permission to do things differently. We are conditioned to believe that changing traditions somehow diminishes them, that opting out means missing out. In reality, the opposite is often true.

Creating new traditions abroad works best when you blend intentionality with spontaneity. Bring one meaningful tradition with you, such as Christmas Eve pajamas or a special ornament, and allow everything else to evolve naturally around your destination.

Children, surprisingly, adapt to new traditions faster than adults. The key is deciding which elements of home to carry with you and which to leave behind. Trying to recreate your exact holiday traditions abroad often leads to exhaustion when local customs and cuisines don’t align with yours.

For many families, the absence of material gift exchanges becomes unexpectedly liberating.

Without the pressure of finding perfect presents, the focus shifts to experiences and time together.

The Pitfalls That Steal Joy (and How to Avoid Them)

Even the most thoughtfully planned holiday abroad can stir unexpected emotions that no amount of five-star service can completely prevent. Knowing the challenges in advance — jet lag, time zone challenges, unfamiliar cultural traditions — is the difference between a holiday that enriches your family and one that leaves everyone counting down the days until it is over.

The most common trap is the expectation of a perfect “Christmas dinner abroad.” Clients often push to recreate the traditional meal, which places impossible pressure on resort chefs. The solution is to embrace your destination’s culinary strengths instead of fighting them.

Homesickness often strikes around day three. The novelty fades and nostalgia creeps in. This is normal and temporary, but it can catch families off guard. The way through is not to over-schedule, but to acknowledge those feelings and create small touchpoints that connect you to home.

The temptation is always to overplan. When you have invested in a special holiday abroad, it feels natural to want every moment to be meaningful. This almost always backfires. The most treasured memories are usually the unplanned ones.

And then there’s technology: set boundaries so that being away feels like being away.

Handling the Family Pushback

The biggest challenge often isn’t logistics; it’s managing family reactions. The moment you announce holiday travel plans, expect some version of “But we always spend Christmas together.”

Start by framing it as “this year” rather than permanent change, and acknowledge that others might feel disappointed. For grandparents, consider a special celebration before or after your trip. Sometimes, a dedicated January visit, without holiday chaos, becomes more meaningful than the rushed Christmas gathering.

The guilt can be intense, especially when you worry about depriving children of “normal” holidays. But kids are remarkably adaptable, and adventure holidays often become their most vivid memories.

Remember: you’re not obligated to prioritize everyone else’s holiday expectations over your family’s well-being.

The Gift That Keeps Giving

The real gift isn’t the destination itself — it’s the chance to step outside your normal life and rediscover what truly matters. These experiences weave themselves into your family story in unexpected and lasting ways.

The holiday season offers a choice: stress and obligation, or wonder and connection. Families who choose to spend it abroad rarely return to traditional celebrations at home — not because they don't value the past, but because they’ve discovered something better: the joy of creating traditions that reflect who they are now.

Ready to rewrite your holiday script? The best time to start planning is now.

LET'S START A NEW TRADITION