What I’ve Learned About Family Travel in a Decade of Planning It

by Tiffany Figueiredo

A colleague of mine — a good one, someone who has been planning travel professionally for years — arrived in South Africa a few months ago to find that three of the restaurants she’d planned around wouldn’t seat her children at dinner. She’d done her research. She’d made reservations. She just hadn’t asked the right question, because nobody told her it was a question worth asking.

That’s how most family trips unravel. Not in the big decisions — the destination, the budget, the hotel — but in the small, unobvious ones that only become visible once you’re already there. After a decade of planning family travel, I’ve come to believe that the difference between a trip that works and one that grinds everyone down comes down to a handful of things most parents never think to ask about in advance.

The Restaurant Problem Nobody Warns You About

Eating out and discovering the local fare is a big part of any vacation. But the restaurant/children problem is more common than people realize, and it goes beyond South Africa. Plenty of excellent restaurants, particularly in Europe, simply don’t accommodate young children — and they don’t always make that clear. Some have no high chairs. Some don’t open until 8 PM. Some will seat you, but make it uncomfortable enough that you’ll wish they’d just refused at the door. If you’re planning independently, the rule is: call, don’t email, and ask specifically. “Do you welcome children?” is too vague. “We have a five-year-old and a seven-year-old. Is your 6:30 seating appropriate, and can we look at the menu in advance?” gets you a real answer.

Trust the Kids. Plan the Logistics

The same principle applies to logistics more broadly. Children don’t struggle with ambitious travel — they adjust to time zones faster than adults, they’re more curious about unfamiliar food than their parents expect, and they’ll remember the trip in ways that surprise you years later. What breaks down is the structural stuff: long unstructured days with no shade and no snacks, airport connections with no stroller-friendly infrastructure, five-star restaurants that expect silence. The trip works when you trust the children and plan the logistics. It fails when you do the reverse.

What the Kids’ Club Photos Don’t Tell You

On the property side, every luxury resort that markets to families leads with the kids’ club: the bright photos, the programming, the certified staff. It’s the easiest thing to photograph and the easiest thing to promise. In my experience, it’s rarely what determines whether the trip actually works.

What matters more is whether the restaurants welcome children at dinner. Whether the staff engage with your kids as people or manage them as an inconvenience. Whether connecting rooms actually connect rather than being separated by a long stretch of hallway. Whether breakfast is available at 7 AM without making you feel like you’re violating the vibe. A property with excellent staff and a mediocre kids’ club will deliver a better family trip than the reverse, and I’ve seen both enough times to be certain of it.

Multigenerational Travel Is Three Vacations Trying to Be One

Multigenerational travel deserves its own mention because it’s the category where I see the most preventable unhappiness. The trap is almost always unintentional: a family books one trip to include grandparents, parents and children, and discovers on arrival that they’ve actually planned three different vacations that now have to coexist. Grandparents want to sleep in and move slowly. Parents want a workout and a real meal and maybe twenty minutes with a book. Children want activity and novelty. These are not compatible rhythms, and pretending they are is how you end up with someone in tears by day three.

The fix is structural. Book a property with enough space that people can actually separate — villas over hotel rooms for groups of six or more, almost always. Build in alternating paces so everyone gets a day that suits them. Plan at least one activity per day that doesn’t require everyone to attend. And build in flexibility around dinner: not every meal needs to be a shared event, and forcing a tasting menu on a four-year-old serves nobody. The families who do multigenerational well treat the logistics as a design problem first. The togetherness tends to follow.

Why Family Travel Doesn’t Reward Spontaneity

The last thing, and perhaps the most useful: family travel does not reward spontaneity the way solo or couples travel can. The relaxed, improvisational approach that works beautifully for two adults falls apart quickly with children in tow. Kids need structure, or at least the illusion of it. The genuinely special experiences — the small restaurants, the private guides, the camps, the boats, the tables worth having — require advance booking in almost every destination worth visiting.

The families who arrive with the right properties locked in, key dinners reserved (with babysitters hired if needed), and marquee activities confirmed consistently have better trips than those who try to sort it out on arrival. That’s been true across every destination I’ve worked in, and it doesn’t get less true as those destinations get more popular.

Most of what goes wrong on family trips is predictable and preventable. The restaurant that won’t seat a five-year-old, the connecting rooms that don’t connect, the multigenerational pace with no room to breathe: none of these are visible from a website. They show up in experience.

If you’re planning a family trip and want to get it right, I’d love to help. Reach me at hello@figtravelco.com or through the website.