A Family of 18 in Cape Town: Lessons from Traveling as a Large Group

There is something both thrilling and intimidating about traveling as a large group. Eighteen people. Different ages, different rhythms, different expectations. On paper, it sounds like chaos. In reality, it became one of the most memorable trips we have ever taken.

We prepared carefully. Or at least, we thought we did.

From hotels and safari bookings to restaurant reservations and long-distance transport, everything was organised weeks in advance. We even created a contribution system to manage group expenses. It felt efficient, controlled, almost effortless.

And yet, travel has a way of revealing the details you didn’t think about.

The Illusion of Being Fully Prepared

We booked three mini vans for our larger excursions. Safari, wine estates, coastal drives. Those were seamless.

What we forgot were the small movements.

The short rides from hotel to restaurant.The transfer from the waterfront back to our accommodation.Even simple supermarket runs.

We assumed Uber XL would be easily available in Cape Town. It wasn’t.

Instead of one vehicle, we often had to book four separate Ubers. Coordinating arrivals, waiting in different corners, texting locations, calculating costs. Four cars became the norm. Even for groceries.

The lesson was simple and humbling: when traveling in a large group, it’s not the long journeys that challenge you. It’s the small distances repeated daily.

• Micro logistics matter as much as major bookings.

• Managing Money Without Managing Tension

• Group travel and money can be delicate.

Before departure, each family contributed monthly to a shared fund. We used one dedicated credit card for restaurant expenses and group activities. It worked beautifully at the beginning. No awkward bill splitting. No counting who ordered what. No tension.

But through the trip, the fund was exhausted.

Instead of continuing with one card and organising constant transfers back to the person paying, we adapted. From that point on, each family paid for themselves at restaurants.

It was simpler. Cleaner. Emotionally lighter.

The experience taught us that structure is important, but flexibility is essential. A system can work perfectly at first and still need adjusting later. And that’s okay.

Staying Together Without Feeling Restricted

One of the fears of large group travel is fragmentation. People drifting apart. Separate plans. Different interests.

What surprised us most was how united we remained.

Safari mornings.

Boat trips.

Seal Island excursions.

Wine tastings.

Coastal walks.

Restaurant evenings.

Almost everyone participated in almost everything.

Of course, there were exceptions. Table Mountain wasn’t for everyone. My grandmother chose to stay at the hotel that day. But the spirit of togetherness defined the trip.

Even supermarket visits became shared adventures. Yes, it meant four Ubers. But it also meant laughter, collective decisions, and shared memories.

Large group travel does not automatically divide people. Sometimes, it strengthens bonds in ways smaller trips never could.

What We Would Do Differently

If we were to organise another trip for 18 people, we would:

• Arrange daily local transport in advance, not only long-distance transfers

• Allocate a flexible contingency budget for unexpected micro costs

• Clarify expense systems for the entire duration of the trip

• Designate meeting points to simplify coordination

Because even the most organised trip will surprise you.

Final Thoughts: Planning Is Essential, Flexibility Is Everything

Traveling as a large group taught us that preparation creates comfort, but adaptability creates harmony.

You can plan hotels, activities, restaurants, and transport. You should. It makes everything smoother.

But the beauty of group travel lies in the unexpected adjustments. The four Ubers instead of one. The change of payment system. The spontaneous moments at the supermarket.

With eighteen people, nothing is ever simple. But nothing is ever dull either.

And perhaps that is the real gift of traveling together.

Not perfection.

But shared imperfection.